The synthesis, cytotoxicity, inhibition of tubulin polymerization data and anti-angiogenetic effects of seven 1,5-disubstituted 1,2,3-triazole analogs and two 1,4-disubstituted 1,2,3-triazole analogs of combretastatin A-1 (1) are reported herein. The biological studies revealed that the 1,5-disubstituted 1,2,3-triazoles 3-methoxy-6-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)benzene-1,2-diol (6), 3-methoxy-6-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)benzene-1,2-diamine (8) and 5-(2,3-difluoro-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole (9) were the three most active compounds regarding inhibition of both tubulin polymerization and angiogenesis. Molecular modeling studies revealed that combretastatins 1 and 2 and analogs 5-11 could be successfully docked into the colchicine binding site of α,β-tubulin.

Akselsen, O.W., Odlo, K., Cheng, J.J., Maccari, G., Botta, M., Hansen, T.V. (2012). Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1. BIOORGANIC & MEDICINAL CHEMISTRY, 20, 234-242 [10.1016/j.bmc.2011.11.010].

Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1.

MACCARI, GIORGIO;BOTTA, MAURIZIO;
2012-01-01

Abstract

The synthesis, cytotoxicity, inhibition of tubulin polymerization data and anti-angiogenetic effects of seven 1,5-disubstituted 1,2,3-triazole analogs and two 1,4-disubstituted 1,2,3-triazole analogs of combretastatin A-1 (1) are reported herein. The biological studies revealed that the 1,5-disubstituted 1,2,3-triazoles 3-methoxy-6-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)benzene-1,2-diol (6), 3-methoxy-6-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)benzene-1,2-diamine (8) and 5-(2,3-difluoro-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole (9) were the three most active compounds regarding inhibition of both tubulin polymerization and angiogenesis. Molecular modeling studies revealed that combretastatins 1 and 2 and analogs 5-11 could be successfully docked into the colchicine binding site of α,β-tubulin.
2012
Akselsen, O.W., Odlo, K., Cheng, J.J., Maccari, G., Botta, M., Hansen, T.V. (2012). Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1. BIOORGANIC & MEDICINAL CHEMISTRY, 20, 234-242 [10.1016/j.bmc.2011.11.010].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/20677
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