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

Rosaria Maria Pipitone, Stefania Grimaudo, Paola Posocco, Erik Laurini, Paolo La Colla, Roberta Loddo, Irene Briguglio, Giampiero Boatto, Maria Silvia Paneni, Sandra Piras, Sabrina Pricl, Antonio Carta, Maurizio Fermeglia, Antonietta Di Cristina

Risultato della ricerca: Articlepeer review

39 Citazioni (Scopus)


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.
Lingua originaleEnglish
pagine (da-a)4151-4167
Numero di pagine17
RivistaEuropean Journal of Medicinal Chemistry
Stato di pubblicazionePublished - 2011

All Science Journal Classification (ASJC) codes

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