Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies
In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst t...
Ausführliche Beschreibung
Autor*in: |
Keskin, Selbi [verfasserIn] Doğan, Şengül Dilem [verfasserIn] Gündüz, Miyase Gözde [verfasserIn] Aleksic, Ivana [verfasserIn] Vojnovic, Sandra [verfasserIn] Lazic, Jelena [verfasserIn] Nikodinovic-Runic, Jasmina [verfasserIn] |
---|
Format: |
E-Artikel |
---|---|
Sprache: |
Englisch |
Erschienen: |
2022 |
---|
Schlagwörter: |
---|
Übergeordnetes Werk: |
Enthalten in: Journal of molecular structure - New York, NY [u.a.] : Elsevier, 1967, 1270 |
---|---|
Übergeordnetes Werk: |
volume:1270 |
DOI / URN: |
10.1016/j.molstruc.2022.133936 |
---|
Katalog-ID: |
ELV008613745 |
---|
LEADER | 01000caa a22002652 4500 | ||
---|---|---|---|
001 | ELV008613745 | ||
003 | DE-627 | ||
005 | 20230524155417.0 | ||
007 | cr uuu---uuuuu | ||
008 | 230509s2022 xx |||||o 00| ||eng c | ||
024 | 7 | |a 10.1016/j.molstruc.2022.133936 |2 doi | |
035 | |a (DE-627)ELV008613745 | ||
035 | |a (ELSEVIER)S0022-2860(22)01589-7 | ||
040 | |a DE-627 |b ger |c DE-627 |e rda | ||
041 | |a eng | ||
082 | 0 | 4 | |a 540 |q DE-600 |
084 | |a 35.00 |2 bkl | ||
100 | 1 | |a Keskin, Selbi |e verfasserin |0 (orcid)0000-0003-0664-9903 |4 aut | |
245 | 1 | 0 | |a Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies |
264 | 1 | |c 2022 | |
336 | |a nicht spezifiziert |b zzz |2 rdacontent | ||
337 | |a Computermedien |b c |2 rdamedia | ||
338 | |a Online-Ressource |b cr |2 rdacarrier | ||
520 | |a In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. | ||
650 | 4 | |a Molecular hybridization | |
650 | 4 | |a Anticancer | |
650 | 4 | |a Antiproliferative | |
650 | 4 | |a Docking | |
650 | 4 | |a Drug-likeness | |
700 | 1 | |a Doğan, Şengül Dilem |e verfasserin |4 aut | |
700 | 1 | |a Gündüz, Miyase Gözde |e verfasserin |0 (orcid)0000-0002-2287-9509 |4 aut | |
700 | 1 | |a Aleksic, Ivana |e verfasserin |0 (orcid)0000-0001-5635-0024 |4 aut | |
700 | 1 | |a Vojnovic, Sandra |e verfasserin |4 aut | |
700 | 1 | |a Lazic, Jelena |e verfasserin |0 (orcid)0000-0003-2618-3573 |4 aut | |
700 | 1 | |a Nikodinovic-Runic, Jasmina |e verfasserin |4 aut | |
773 | 0 | 8 | |i Enthalten in |t Journal of molecular structure |d New York, NY [u.a.] : Elsevier, 1967 |g 1270 |h Online-Ressource |w (DE-627)302469745 |w (DE-600)1491504-2 |w (DE-576)255266626 |x 0022-2860 |7 nnns |
773 | 1 | 8 | |g volume:1270 |
912 | |a GBV_USEFLAG_U | ||
912 | |a SYSFLAG_U | ||
912 | |a GBV_ELV | ||
912 | |a SSG-OLC-PHA | ||
912 | |a GBV_ILN_20 | ||
912 | |a GBV_ILN_22 | ||
912 | |a GBV_ILN_23 | ||
912 | |a GBV_ILN_24 | ||
912 | |a GBV_ILN_31 | ||
912 | |a GBV_ILN_32 | ||
912 | |a GBV_ILN_40 | ||
912 | |a GBV_ILN_60 | ||
912 | |a GBV_ILN_62 | ||
912 | |a GBV_ILN_63 | ||
912 | |a GBV_ILN_65 | ||
912 | |a GBV_ILN_69 | ||
912 | |a GBV_ILN_70 | ||
912 | |a GBV_ILN_73 | ||
912 | |a GBV_ILN_74 | ||
912 | |a GBV_ILN_90 | ||
912 | |a GBV_ILN_95 | ||
912 | |a GBV_ILN_100 | ||
912 | |a GBV_ILN_101 | ||
912 | |a GBV_ILN_105 | ||
912 | |a GBV_ILN_110 | ||
912 | |a GBV_ILN_150 | ||
912 | |a GBV_ILN_151 | ||
912 | |a GBV_ILN_224 | ||
912 | |a GBV_ILN_370 | ||
912 | |a GBV_ILN_602 | ||
912 | |a GBV_ILN_702 | ||
912 | |a GBV_ILN_2003 | ||
912 | |a GBV_ILN_2004 | ||
912 | |a GBV_ILN_2005 | ||
912 | |a GBV_ILN_2011 | ||
912 | |a GBV_ILN_2014 | ||
912 | |a GBV_ILN_2015 | ||
912 | |a GBV_ILN_2020 | ||
912 | |a GBV_ILN_2021 | ||
912 | |a GBV_ILN_2025 | ||
912 | |a GBV_ILN_2027 | ||
912 | |a GBV_ILN_2034 | ||
912 | |a GBV_ILN_2038 | ||
912 | |a GBV_ILN_2044 | ||
912 | |a GBV_ILN_2048 | ||
912 | |a GBV_ILN_2049 | ||
912 | |a GBV_ILN_2050 | ||
912 | |a GBV_ILN_2056 | ||
912 | |a GBV_ILN_2059 | ||
912 | |a GBV_ILN_2061 | ||
912 | |a GBV_ILN_2064 | ||
912 | |a GBV_ILN_2065 | ||
912 | |a GBV_ILN_2068 | ||
912 | |a GBV_ILN_2111 | ||
912 | |a GBV_ILN_2112 | ||
912 | |a GBV_ILN_2113 | ||
912 | |a GBV_ILN_2118 | ||
912 | |a GBV_ILN_2122 | ||
912 | |a GBV_ILN_2129 | ||
912 | |a GBV_ILN_2143 | ||
912 | |a GBV_ILN_2147 | ||
912 | |a GBV_ILN_2148 | ||
912 | |a GBV_ILN_2152 | ||
912 | |a GBV_ILN_2153 | ||
912 | |a GBV_ILN_2190 | ||
912 | |a GBV_ILN_2336 | ||
912 | |a GBV_ILN_2507 | ||
912 | |a GBV_ILN_2522 | ||
912 | |a GBV_ILN_4035 | ||
912 | |a GBV_ILN_4037 | ||
912 | |a GBV_ILN_4112 | ||
912 | |a GBV_ILN_4125 | ||
912 | |a GBV_ILN_4126 | ||
912 | |a GBV_ILN_4242 | ||
912 | |a GBV_ILN_4251 | ||
912 | |a GBV_ILN_4305 | ||
912 | |a GBV_ILN_4313 | ||
912 | |a GBV_ILN_4323 | ||
912 | |a GBV_ILN_4324 | ||
912 | |a GBV_ILN_4326 | ||
912 | |a GBV_ILN_4333 | ||
912 | |a GBV_ILN_4334 | ||
912 | |a GBV_ILN_4335 | ||
912 | |a GBV_ILN_4338 | ||
912 | |a GBV_ILN_4393 | ||
936 | b | k | |a 35.00 |j Chemie: Allgemeines |
951 | |a AR | ||
952 | |d 1270 |
author_variant |
s k sk ş d d şd şdd m g g mg mgg i a ia s v sv j l jl j n r jnr |
---|---|
matchkey_str |
article:00222860:2022----::noeaehdaoeeiaiesnhssyooiiysesetnm |
hierarchy_sort_str |
2022 |
bklnumber |
35.00 |
publishDate |
2022 |
allfields |
10.1016/j.molstruc.2022.133936 doi (DE-627)ELV008613745 (ELSEVIER)S0022-2860(22)01589-7 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Keskin, Selbi verfasserin (orcid)0000-0003-0664-9903 aut Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness Doğan, Şengül Dilem verfasserin aut Gündüz, Miyase Gözde verfasserin (orcid)0000-0002-2287-9509 aut Aleksic, Ivana verfasserin (orcid)0000-0001-5635-0024 aut Vojnovic, Sandra verfasserin aut Lazic, Jelena verfasserin (orcid)0000-0003-2618-3573 aut Nikodinovic-Runic, Jasmina verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1270 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1270 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1270 |
spelling |
10.1016/j.molstruc.2022.133936 doi (DE-627)ELV008613745 (ELSEVIER)S0022-2860(22)01589-7 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Keskin, Selbi verfasserin (orcid)0000-0003-0664-9903 aut Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness Doğan, Şengül Dilem verfasserin aut Gündüz, Miyase Gözde verfasserin (orcid)0000-0002-2287-9509 aut Aleksic, Ivana verfasserin (orcid)0000-0001-5635-0024 aut Vojnovic, Sandra verfasserin aut Lazic, Jelena verfasserin (orcid)0000-0003-2618-3573 aut Nikodinovic-Runic, Jasmina verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1270 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1270 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1270 |
allfields_unstemmed |
10.1016/j.molstruc.2022.133936 doi (DE-627)ELV008613745 (ELSEVIER)S0022-2860(22)01589-7 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Keskin, Selbi verfasserin (orcid)0000-0003-0664-9903 aut Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness Doğan, Şengül Dilem verfasserin aut Gündüz, Miyase Gözde verfasserin (orcid)0000-0002-2287-9509 aut Aleksic, Ivana verfasserin (orcid)0000-0001-5635-0024 aut Vojnovic, Sandra verfasserin aut Lazic, Jelena verfasserin (orcid)0000-0003-2618-3573 aut Nikodinovic-Runic, Jasmina verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1270 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1270 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1270 |
allfieldsGer |
10.1016/j.molstruc.2022.133936 doi (DE-627)ELV008613745 (ELSEVIER)S0022-2860(22)01589-7 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Keskin, Selbi verfasserin (orcid)0000-0003-0664-9903 aut Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness Doğan, Şengül Dilem verfasserin aut Gündüz, Miyase Gözde verfasserin (orcid)0000-0002-2287-9509 aut Aleksic, Ivana verfasserin (orcid)0000-0001-5635-0024 aut Vojnovic, Sandra verfasserin aut Lazic, Jelena verfasserin (orcid)0000-0003-2618-3573 aut Nikodinovic-Runic, Jasmina verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1270 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1270 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1270 |
allfieldsSound |
10.1016/j.molstruc.2022.133936 doi (DE-627)ELV008613745 (ELSEVIER)S0022-2860(22)01589-7 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Keskin, Selbi verfasserin (orcid)0000-0003-0664-9903 aut Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness Doğan, Şengül Dilem verfasserin aut Gündüz, Miyase Gözde verfasserin (orcid)0000-0002-2287-9509 aut Aleksic, Ivana verfasserin (orcid)0000-0001-5635-0024 aut Vojnovic, Sandra verfasserin aut Lazic, Jelena verfasserin (orcid)0000-0003-2618-3573 aut Nikodinovic-Runic, Jasmina verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1270 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1270 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.00 Chemie: Allgemeines AR 1270 |
language |
English |
source |
Enthalten in Journal of molecular structure 1270 volume:1270 |
sourceStr |
Enthalten in Journal of molecular structure 1270 volume:1270 |
format_phy_str_mv |
Article |
bklname |
Chemie: Allgemeines |
institution |
findex.gbv.de |
topic_facet |
Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness |
dewey-raw |
540 |
isfreeaccess_bool |
false |
container_title |
Journal of molecular structure |
authorswithroles_txt_mv |
Keskin, Selbi @@aut@@ Doğan, Şengül Dilem @@aut@@ Gündüz, Miyase Gözde @@aut@@ Aleksic, Ivana @@aut@@ Vojnovic, Sandra @@aut@@ Lazic, Jelena @@aut@@ Nikodinovic-Runic, Jasmina @@aut@@ |
publishDateDaySort_date |
2022-01-01T00:00:00Z |
hierarchy_top_id |
302469745 |
dewey-sort |
3540 |
id |
ELV008613745 |
language_de |
englisch |
fullrecord |
<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">ELV008613745</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230524155417.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">230509s2022 xx |||||o 00| ||eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1016/j.molstruc.2022.133936</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)ELV008613745</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(ELSEVIER)S0022-2860(22)01589-7</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rda</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">540</subfield><subfield code="q">DE-600</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.00</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Keskin, Selbi</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0003-0664-9903</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2022</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Molecular hybridization</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Anticancer</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiproliferative</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Docking</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Drug-likeness</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Doğan, Şengül Dilem</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Gündüz, Miyase Gözde</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0002-2287-9509</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Aleksic, Ivana</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0001-5635-0024</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Vojnovic, Sandra</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Lazic, Jelena</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0003-2618-3573</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Nikodinovic-Runic, Jasmina</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Journal of molecular structure</subfield><subfield code="d">New York, NY [u.a.] : Elsevier, 1967</subfield><subfield code="g">1270</subfield><subfield code="h">Online-Ressource</subfield><subfield code="w">(DE-627)302469745</subfield><subfield code="w">(DE-600)1491504-2</subfield><subfield code="w">(DE-576)255266626</subfield><subfield code="x">0022-2860</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:1270</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_20</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_22</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_23</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_31</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_32</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_40</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_60</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_63</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_65</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_73</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_74</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_90</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_95</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_100</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_101</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_105</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_150</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_151</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_224</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_370</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_602</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_702</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2003</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2004</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2005</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2011</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2014</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2015</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2020</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2021</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2025</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2027</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2034</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2038</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2044</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2048</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2049</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2050</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2056</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2059</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2061</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2064</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2065</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2068</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2111</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2113</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2118</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2122</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2129</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2143</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2147</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2148</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2152</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2153</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2190</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2336</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2507</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2522</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4035</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4125</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4126</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4242</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4251</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4313</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4323</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4324</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4326</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4333</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4334</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4335</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4338</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4393</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.00</subfield><subfield code="j">Chemie: Allgemeines</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">1270</subfield></datafield></record></collection>
|
author |
Keskin, Selbi |
spellingShingle |
Keskin, Selbi ddc 540 bkl 35.00 misc Molecular hybridization misc Anticancer misc Antiproliferative misc Docking misc Drug-likeness Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies |
authorStr |
Keskin, Selbi |
ppnlink_with_tag_str_mv |
@@773@@(DE-627)302469745 |
format |
electronic Article |
dewey-ones |
540 - Chemistry & allied sciences |
delete_txt_mv |
keep |
author_role |
aut aut aut aut aut aut aut |
collection |
elsevier |
remote_str |
true |
illustrated |
Not Illustrated |
issn |
0022-2860 |
topic_title |
540 DE-600 35.00 bkl Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness |
topic |
ddc 540 bkl 35.00 misc Molecular hybridization misc Anticancer misc Antiproliferative misc Docking misc Drug-likeness |
topic_unstemmed |
ddc 540 bkl 35.00 misc Molecular hybridization misc Anticancer misc Antiproliferative misc Docking misc Drug-likeness |
topic_browse |
ddc 540 bkl 35.00 misc Molecular hybridization misc Anticancer misc Antiproliferative misc Docking misc Drug-likeness |
format_facet |
Elektronische Aufsätze Aufsätze Elektronische Ressource |
format_main_str_mv |
Text Zeitschrift/Artikel |
carriertype_str_mv |
cr |
hierarchy_parent_title |
Journal of molecular structure |
hierarchy_parent_id |
302469745 |
dewey-tens |
540 - Chemistry |
hierarchy_top_title |
Journal of molecular structure |
isfreeaccess_txt |
false |
familylinks_str_mv |
(DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 |
title |
Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies |
ctrlnum |
(DE-627)ELV008613745 (ELSEVIER)S0022-2860(22)01589-7 |
title_full |
Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies |
author_sort |
Keskin, Selbi |
journal |
Journal of molecular structure |
journalStr |
Journal of molecular structure |
lang_code |
eng |
isOA_bool |
false |
dewey-hundreds |
500 - Science |
recordtype |
marc |
publishDateSort |
2022 |
contenttype_str_mv |
zzz |
author_browse |
Keskin, Selbi Doğan, Şengül Dilem Gündüz, Miyase Gözde Aleksic, Ivana Vojnovic, Sandra Lazic, Jelena Nikodinovic-Runic, Jasmina |
container_volume |
1270 |
class |
540 DE-600 35.00 bkl |
format_se |
Elektronische Aufsätze |
author-letter |
Keskin, Selbi |
doi_str_mv |
10.1016/j.molstruc.2022.133936 |
normlink |
(ORCID)0000-0003-0664-9903 (ORCID)0000-0002-2287-9509 (ORCID)0000-0001-5635-0024 (ORCID)0000-0003-2618-3573 |
normlink_prefix_str_mv |
(orcid)0000-0003-0664-9903 (orcid)0000-0002-2287-9509 (orcid)0000-0001-5635-0024 (orcid)0000-0003-2618-3573 |
dewey-full |
540 |
author2-role |
verfasserin |
title_sort |
indole-based hydrazone derivatives: synthesis, cytotoxicity assessment, and molecular modeling studies |
title_auth |
Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies |
abstract |
In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. |
abstractGer |
In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. |
abstract_unstemmed |
In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies. |
collection_details |
GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 |
title_short |
Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies |
remote_bool |
true |
author2 |
Doğan, Şengül Dilem Gündüz, Miyase Gözde Aleksic, Ivana Vojnovic, Sandra Lazic, Jelena Nikodinovic-Runic, Jasmina |
author2Str |
Doğan, Şengül Dilem Gündüz, Miyase Gözde Aleksic, Ivana Vojnovic, Sandra Lazic, Jelena Nikodinovic-Runic, Jasmina |
ppnlink |
302469745 |
mediatype_str_mv |
c |
isOA_txt |
false |
hochschulschrift_bool |
false |
doi_str |
10.1016/j.molstruc.2022.133936 |
up_date |
2024-07-06T20:18:26.507Z |
_version_ |
1803862258754781184 |
fullrecord_marcxml |
<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">ELV008613745</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230524155417.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">230509s2022 xx |||||o 00| ||eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1016/j.molstruc.2022.133936</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)ELV008613745</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(ELSEVIER)S0022-2860(22)01589-7</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rda</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">540</subfield><subfield code="q">DE-600</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.00</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Keskin, Selbi</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0003-0664-9903</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2022</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">In the present study, we report the synthesis, cytotoxicity determination and molecular modeling studies of twelve novel indole-based hydrazone derivatives (IH1-IH12). To obtain the target molecules, initially, 1H-indole-2-carboxylic acid and ethanol were heated in the presence of an acid catalyst to yield ethyl 1H-indole-2-carboxylate. Following the hydrazinolyzation of the ester moiety, the resulting compound, 1H-indole-2-carbohydrazide reacted with appropriate benzaldehyde derivatives to obtain IH1-IH12. The proposed chemical structures of all compounds were confirmed by their 1H NMR, 13C NMR, IR, and HRMS data. Additionally, the configuration of C=N bond in IH8 was determined as (E) by applying 2D NMR technique, NOESY. Subsequently, the compounds were tested against both colon cancer (HCT116) and lung cancer (A549), as well as healthy lung fibroblast (MRC-5) cell lines to determine their potential as anticancer agents and their selectivity indexes (SI). Based on the obtained data from the antiproliferative MTT assay, HCT116 cell line was more sensitive to our molecules compared to A549. Furthermore, lipophilic halogens were preferable substituents on the phenyl ring for the selective toxicity against cancer cell lines. Drug-likeness analysis carried out by calculating important physicochemical properties of IH1-IH12 confirmed that they all obey Lipinski's rule of five. Finally, hypoxia inducible factor (HIF)-1α was suggested as the potential biological target of the compounds through molecular docking studies.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Molecular hybridization</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Anticancer</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Antiproliferative</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Docking</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Drug-likeness</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Doğan, Şengül Dilem</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Gündüz, Miyase Gözde</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0002-2287-9509</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Aleksic, Ivana</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0001-5635-0024</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Vojnovic, Sandra</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Lazic, Jelena</subfield><subfield code="e">verfasserin</subfield><subfield code="0">(orcid)0000-0003-2618-3573</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Nikodinovic-Runic, Jasmina</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Journal of molecular structure</subfield><subfield code="d">New York, NY [u.a.] : Elsevier, 1967</subfield><subfield code="g">1270</subfield><subfield code="h">Online-Ressource</subfield><subfield code="w">(DE-627)302469745</subfield><subfield code="w">(DE-600)1491504-2</subfield><subfield code="w">(DE-576)255266626</subfield><subfield code="x">0022-2860</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:1270</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_20</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_22</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_23</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_31</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_32</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_40</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_60</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_63</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_65</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_73</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_74</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_90</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_95</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_100</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_101</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_105</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_150</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_151</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_224</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_370</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_602</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_702</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2003</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2004</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2005</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2011</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2014</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2015</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2020</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2021</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2025</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2027</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2034</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2038</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2044</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2048</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2049</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2050</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2056</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2059</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2061</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2064</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2065</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2068</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2111</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2113</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2118</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2122</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2129</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2143</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2147</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2148</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2152</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2153</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2190</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2336</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2507</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2522</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4035</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4125</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4126</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4242</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4251</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4313</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4323</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4324</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4326</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4333</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4334</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4335</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4338</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4393</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.00</subfield><subfield code="j">Chemie: Allgemeines</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">1270</subfield></datafield></record></collection>
|
score |
7.3979836 |