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Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization. 2007
Romeo Romagnoli, and
Pier Giovanni Baraldi, and
Maria Dora Carrion, and
Carlota Lopez Cara, and
Delia Preti, and
Francesca Fruttarolo, and
Maria Giovanna Pavani, and
Mojgan Aghazadeh Tabrizi, and
Manlio Tolomeo, and
Stefania Grimaudo, and
Antonella Di Cristina, and
Jan Balzarini, and
John A Hadfield, and
Andrea Brancale, and
Ernest Hamel
Dipartimento di Scienze Farmaceutiche, Università di Ferrara, 44100 Ferrara, Italy.
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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