Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells.

Org Biomol Chem

Laboratório de Química Farmacêutica, Faculdade de Farmácia da Universidade de Coimbra, Poló das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal.

Published: February 2013

A series of new oleanane imidazole carbamates, N-acylimidazoles or N-alkylimidazoles were synthesized, characterized and evaluated for their antiproliferative activity in AsPC-1 pancreatic cancer cells. Structure-activity relationship analysis revealed that the N-alkylimidazole 27 was the most active compound with apoptosis induction abilities correlated with upregulation of NOXA and downregulation of Bcl-xL. The antiproliferative activity of compound 27 was further tested in more solid tumor cell lines with IC(50) values lower than 1 μM.

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http://dx.doi.org/10.1039/c3ob00011gDOI Listing

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