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3-Aryl-2-[1H-benzotriazol-1-yl]acrylonitriles: a novel class of potent tubulin inhibitors.

Abstract：

:During a screening for compounds that could act against Mycobacterium tuberculosis, a series of new cellular antiproliferative agents was identified. The most cytotoxic molecules were evaluated against a panel of human cell lines derived from hematological and solid human tumors. In particular, (E)-2-(1H-benzo[d] [1,2,3]triazol-1-yl)-3-(4-methoxyphenyl)acrylonitrile (1) was found to be of a potency comparable to etoposide and greater than 6-mercaptopurine in all cell lines tested. Accordingly, a synthesis of a new series of (E)-2-(5,6-dichloro-1H-benzo[d] [1,2,3]triazol-1-yl)-3-(4-R-phenyl)acrylonitriles was conducted in order to extend the studies of structure-activity relationship (SAR) for this class of molecules. With the aim to evaluate if 3-aryl-2-[1H-benzotriazol-1-yl]acrylonitriles were able to act like tubulin binding agents, the effects on cell cycle distribution of the most active compounds (1, 2a, 3 and 4) were analyzed in K562 cells. A detailed molecular modeling study of the putative binding mode of this series of compounds on tubulin is also reported.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Carta A,Briguglio I,Piras S,Boatto G,La Colla P,Loddo R,Tolomeo M,Grimaudo S,Di Cristina A,Pipitone RM,Laurini E,Paneni MS,Posocco P,Fermeglia M,Pricl S

doi

10.1016/j.ejmech.2011.06.018

subject

Has Abstract

pub_date

2011-09-01 00:00:00

pages

4151-67

issue

9

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00494-6

journal_volume

46

pub_type

杂志文章

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