Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization
A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antip...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Zhang, Ruiqiang [verfasserIn] Mo, Hualong [verfasserIn] Ma, Yan-Yan [verfasserIn] Zhao, Deng-Gao [verfasserIn] Zhang, Kun [verfasserIn] Zhang, Tingwen [verfasserIn] Chen, Xuecheng [verfasserIn] Zheng, Xi [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2021 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Bioorganic & medicinal chemistry letters - Amsterdam [u.a.] : Elsevier Science, 1991, 40 |
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| Übergeordnetes Werk: |
volume:40 |
| DOI / URN: |
10.1016/j.bmcl.2021.127968 |
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| Katalog-ID: |
ELV005918545 |
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| 245 | 1 | 0 | |a Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization |
| 264 | 1 | |c 2021 | |
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| 520 | |a A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. | ||
| 650 | 4 | |a Oxazole | |
| 650 | 4 | |a Tubulin polymerization | |
| 650 | 4 | |a Structure–activity relationships | |
| 650 | 4 | |a Cytotoxicity | |
| 650 | 4 | |a ABT751 | |
| 700 | 1 | |a Mo, Hualong |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Yan-Yan |e verfasserin |0 (orcid)0000-0002-8639-712X |4 aut | |
| 700 | 1 | |a Zhao, Deng-Gao |e verfasserin |0 (orcid)0000-0003-1143-4106 |4 aut | |
| 700 | 1 | |a Zhang, Kun |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Tingwen |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Xuecheng |e verfasserin |4 aut | |
| 700 | 1 | |a Zheng, Xi |e verfasserin |4 aut | |
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10.1016/j.bmcl.2021.127968 doi (DE-627)ELV005918545 (ELSEVIER)S0960-894X(21)00194-3 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Zhang, Ruiqiang verfasserin aut Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. Oxazole Tubulin polymerization Structure–activity relationships Cytotoxicity ABT751 Mo, Hualong verfasserin aut Ma, Yan-Yan verfasserin (orcid)0000-0002-8639-712X aut Zhao, Deng-Gao verfasserin (orcid)0000-0003-1143-4106 aut Zhang, Kun verfasserin aut Zhang, Tingwen verfasserin aut Chen, Xuecheng verfasserin aut Zheng, Xi verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 40 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:40 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-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 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 40 |
| spelling |
10.1016/j.bmcl.2021.127968 doi (DE-627)ELV005918545 (ELSEVIER)S0960-894X(21)00194-3 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Zhang, Ruiqiang verfasserin aut Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. Oxazole Tubulin polymerization Structure–activity relationships Cytotoxicity ABT751 Mo, Hualong verfasserin aut Ma, Yan-Yan verfasserin (orcid)0000-0002-8639-712X aut Zhao, Deng-Gao verfasserin (orcid)0000-0003-1143-4106 aut Zhang, Kun verfasserin aut Zhang, Tingwen verfasserin aut Chen, Xuecheng verfasserin aut Zheng, Xi verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 40 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:40 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-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 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 40 |
| allfields_unstemmed |
10.1016/j.bmcl.2021.127968 doi (DE-627)ELV005918545 (ELSEVIER)S0960-894X(21)00194-3 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Zhang, Ruiqiang verfasserin aut Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. Oxazole Tubulin polymerization Structure–activity relationships Cytotoxicity ABT751 Mo, Hualong verfasserin aut Ma, Yan-Yan verfasserin (orcid)0000-0002-8639-712X aut Zhao, Deng-Gao verfasserin (orcid)0000-0003-1143-4106 aut Zhang, Kun verfasserin aut Zhang, Tingwen verfasserin aut Chen, Xuecheng verfasserin aut Zheng, Xi verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 40 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:40 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-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 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 40 |
| allfieldsGer |
10.1016/j.bmcl.2021.127968 doi (DE-627)ELV005918545 (ELSEVIER)S0960-894X(21)00194-3 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Zhang, Ruiqiang verfasserin aut Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. Oxazole Tubulin polymerization Structure–activity relationships Cytotoxicity ABT751 Mo, Hualong verfasserin aut Ma, Yan-Yan verfasserin (orcid)0000-0002-8639-712X aut Zhao, Deng-Gao verfasserin (orcid)0000-0003-1143-4106 aut Zhang, Kun verfasserin aut Zhang, Tingwen verfasserin aut Chen, Xuecheng verfasserin aut Zheng, Xi verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 40 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:40 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-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 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 40 |
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10.1016/j.bmcl.2021.127968 doi (DE-627)ELV005918545 (ELSEVIER)S0960-894X(21)00194-3 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Zhang, Ruiqiang verfasserin aut Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. Oxazole Tubulin polymerization Structure–activity relationships Cytotoxicity ABT751 Mo, Hualong verfasserin aut Ma, Yan-Yan verfasserin (orcid)0000-0002-8639-712X aut Zhao, Deng-Gao verfasserin (orcid)0000-0003-1143-4106 aut Zhang, Kun verfasserin aut Zhang, Tingwen verfasserin aut Chen, Xuecheng verfasserin aut Zheng, Xi verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 40 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:40 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-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 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 40 |
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Zhang, Ruiqiang @@aut@@ Mo, Hualong @@aut@@ Ma, Yan-Yan @@aut@@ Zhao, Deng-Gao @@aut@@ Zhang, Kun @@aut@@ Zhang, Tingwen @@aut@@ Chen, Xuecheng @@aut@@ Zheng, Xi @@aut@@ |
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| author |
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synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization |
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Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization |
| abstract |
A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. |
| abstractGer |
A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. |
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A series of 5-phenyloxazole-2-carboxylic acid derivatives were synthesized, and their structure–activity relationships (SARs) were studied. N,5-diphenyloxazole-2-carboxamides 6, 7, and 9, which mimicked ABT751, showed improved cytotoxicity compared with ABT751. Compound 9 exhibited the highest antiproliferative activities against Hela A549, and HepG2 cancer cell lines, with IC50 values of 0.78, 1.08, and 1.27 μM, respectively. Furthermore, compound 9 showed selectivity for human cancer cells over normal cells, and this selectivity was greater than those of ABT751 and colchicine. Preliminary mechanism studies suggested that compound 9 inhibited tubulin polymerization and led to cell cycle arrest at G2/M phase. Molecular docking studies indicated that compound 9 bound to the colchicine binding site of tubulin. Our findings provided insights into useful SARs for further structural modification of inhibitors of tubulin polymerization. |
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Synthesis and structure–activity relationships of 5-phenyloxazole-2-carboxylic acid derivatives as novel inhibitors of tubulin polymerization |
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|
| score |
7.401288 |