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Synthesis of novel antimitotic agents based on 2-amino-3-aroyl-5-(hetero)arylethynyl thiophene derivatives

Romagnoli, Romeo, Baraldi, Pier Giovanni, Cruz-Lopez, Olga, Tolomeo, Manlio, Di Cristina, Antonietta, Pipitone, Rosaria Maria, Grimaudo, Stefania, Balzarini, Jan, Brancale, Andrea ORCID: and Hamel, Ernest 2011. Synthesis of novel antimitotic agents based on 2-amino-3-aroyl-5-(hetero)arylethynyl thiophene derivatives. Biorganic and Medicinal Chemistry Letters 21 (9) , pp. 2746-2751. 10.1016/j.bmcl.2010.11.083

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Microtubules are dynamic structures that play a crucial role in cellular division and are recognized as an important target for cancer therapy. In search of new compounds with strong antiproliferative activity and simple molecular structure, a new series of 2-amino-3-(3′,4′,5′-trimethoxybenzoyl)-5-(hetero)aryl ethynyl thiophene derivatives was prepared by the Sonogashira coupling reaction of the corresponding 5-bromothiophenes with several (hetero)aryl acetylenes. When these compounds were analyzed in vitro for their inhibition of cell proliferation, the 2- and 3-thiophenyl acetylene derivatives were the most powerful compounds, both of which exerted cytostatic effects at submicromolar concentrations. In contrast, the presence of a more flexible ethyl chain between the (hetero)aryl and the 5-position of the thiophene ring resulted in significant reduction in activity relative to the 5-(hetero)aryl acetylene substituted derivatives. The effects of a selected series of compounds on cell cycle progression correlated well with their strong antiproliferative activity and inhibition of tubulin polymerization. We found that the antiproliferative effects of the most active compounds were associated with increase of the proportion of cells in the G2/M and sub-G1 phases of the cell cycle.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords: Thiophene; Inhibition of tubulin polymerization; Inhibition of tumor cell growth; Antiproliferative agents
Publisher: Elsevier
ISSN: 0960-894X
Last Modified: 17 Oct 2022 10:14

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