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1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin.

Abstract：

:A series of cis-restricted 1,5-disubstituted 1,2,3-triazole analogues of combretastatin A-4 (1) have been prepared. The triazole 12f, 2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)aniline, displayed potent cytotoxic activity against several cancer cell lines with IC(50) values in the nanomolar range. The ability of triazoles to inhibit tubulin polymerization has been evaluated, and 12f inhibited tubulin polymerization with IC(50)=4.8microM. Molecular modeling experiments involving 12f and the colchicine binding site of alpha,beta-tubulin showed that the triazole moiety interacts with beta-tubulin via hydrogen bonding with several amino acids.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Odlo K,Hentzen J,dit Chabert JF,Ducki S,Gani OA,Sylte I,Skrede M,Flørenes VA,Hansen TV

doi

10.1016/j.bmc.2008.03.049

subject

Has Abstract

pub_date

2008-05-01 00:00:00

pages

4829-38

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00274-5

journal_volume

16

pub_type

杂志文章

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