Title: Design, synthesis and structure-activity relationship of 2-(3',4',5'-trimethoxybenzoyl)-benzo[b]furan derivatives as a novel class of inhibitors of tubulin polymerization
Authors: Romagnoli, Romeo ×
Baraldi, Pier Giovanni
Carrion, Maria Dora
Cara, Carlota Lopez
Cruz-Lopez, Olga
Tolomeo, Manlio
Grimaudo, Stefania
Cristina, Antonietta Di
Pipitone, Maria Rosaria
Balzarini, Jan
Zonta, Nicola
Brancale, Andrea
Hamel, Ernest #
Issue Date: Oct-2009
Publisher: Pergamon
Series Title: Bioorganic & Medicinal Chemistry vol:17 issue:19 pages:6862-6871
Abstract: The biological importance of microtubules in mitosis and cell division makes them an interesting target for the development of anticancer agents. Small molecules such as benzo[b]furans are attractive as inhibitors of tubulin polymerization. Thus, a new class of inhibitors of tubulin polymerization based on the 2-(3',4',5'-trimethoxybenzoyl)-benzo[b]furan molecular skeleton, with electron-donating (Me, OMe or OH) or electron-withdrawing (F, Cl and Br) substituents on the benzene ring, was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization and cell cycle effects. Adding a methyl group at the C-3 position resulted in increased activity. The most promising compound in this series was 2-(3',4',5'-trimethoxybenzoyl)-3-methyl-6-ethoxy-benzo[b]furan, which inhibits cancer cell growth at nanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.
ISSN: 0968-0896
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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