Issue 10, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Ana S. Leal,abc   Rui Wang,c   Jorge A. R. Salvador*ab  and  Yongkui Jing*c  

* Corresponding authors

a Laboratório de Química Farmacêutica, Faculdade de Farmácia da Universidade de Coimbra, Poló das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal
E-mail: salvador@ci.uc.pt
Fax: +351-239-488-503
Tel: +351-239-488-400

b CNC-Centro de Neurociências e Biologia Celular, Universidade de Coimbra, 3000-517 Coimbra, Portugal

c Division of Hematology/Oncology, The Tisch Cancer Institute, Mount Sinai School of Medicine, New York, 10029 NY, USA
E-mail: yongkui.jing@mssm.edu
Fax: +1-212-996-5787
Tel: +1-212-241-6775

Abstract

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 IC50 values lower than 1 μM.

Graphical abstract: Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells

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Article information

DOI
https://doi.org/10.1039/C3OB00011G
Article type
Paper
Submitted
23 Oct 2012
Accepted
16 Jan 2013
First published
16 Jan 2013

Org. Biomol. Chem., 2013,11, 1726-1738

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

A. S. Leal, R. Wang, J. A. R. Salvador and Y. Jing, Org. Biomol. Chem., 2013, 11, 1726 DOI: 10.1039/C3OB00011G

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