Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[b]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization
Journal of Medicinal Chemistry2007Vol. 50(9), pp. 2273–2277
Citations Over TimeTop 10% of 2007 papers
Romeo Romagnoli, Pier Giovanni Baraldi, María Dora Carriòn, M Cara, Delia Preti, Francesca Fruttarolo, Maria Giovanna Pavani, Mojgan Aghazadeh Tabrizi, Manlio Tolomeo, Stefania Grimaudo, Antonella Di Cristina, Jan Balzarini, John A. Hadfield, Andrea Brancale, Ernest Hamel
Abstract
Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.
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