Facile one-pot syntheses of new C-28 esters of oleanolic acid and studies on their antiproliferative effect on T cells

Author:

Ali Muhammad S.1,Ahmed Ghafoor1,Mesaik Muhammad A.23,Shah Muhammad R.1,Lateef Mehreen4,Ali Muhammad I.1

Affiliation:

1. H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences , University of Karachi , Karachi 75270 , Pakistan

2. Panjwani Center for Molecular Medicine and Drug Research, International Centre for Chemical and Biological Sciences , University of Karachi , Karachi 75270 , Pakistan

3. Faculty of Medicine , University of Tabuk , P.O. Box 741 , Tabuk , Saudi Arabia

4. Multi Disciplinary Research Laboratory , Bahria University Medical and Dental College , Karachi , Pakistan

Abstract

Abstract Structure-activity relationship studies on oleanolic acid (1) have resulted in facile syntheses of its new C-28 esters 2–7 by way of one-pot reaction of 1 with a variety of alkylating agents. Oleanolic acid and its new esters were studied for their in vitro antiproliferative effect on healthy human peripheral blood mononuclear cell isolated phytohemagglutinin activated T cells. Results showed that compounds 1, 3, and 5 exhibited significant inhibitory activity on T-cell proliferation. Compound 5 was found to be the most potent, with an IC50 value of 4.249 μg/mL, among all tested compounds, and its activity could be attributed to the presence of bromine atom in the molecule.

Publisher

Walter de Gruyter GmbH

Subject

General Biochemistry, Genetics and Molecular Biology

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