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...
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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:	Molecular hybridization Anticancer Antiproliferative Docking Drug-likeness

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

Internformat


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245	1	0	\|a Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies
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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
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912			\|a GBV_ILN_65
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912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_74
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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
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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

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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
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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
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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
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title	Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies
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title_full	Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies
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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.
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title_short	Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies
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author2	Doğan, Şengül Dilem Gündüz, Miyase Gözde Aleksic, Ivana Vojnovic, Sandra Lazic, Jelena Nikodinovic-Runic, Jasmina
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Indole-based hydrazone derivatives: Synthesis, cytotoxicity assessment, and molecular modeling studies

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