New chalcones and thiopyrimidine analogues derived from mefenamic acid: microwave-assisted synthesis, anti-HIV activity and cytotoxicity as antileukemic agents
Author:
Al-Hazam Hanan A.1, Al-Shamkani Zeki A.1, Al-Masoudi Najim A.1, Saeed Bahjat A.2, Pannecouque Christophe3
Affiliation:
1. Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq 2. Department of Chemistry, College of Education, University of Basrah, Basrah, Iraq 3. Rega Institute for Medical Research, Katholieke Universiteit, Leuven, Leuven, Belgium
Abstract
Abstract
The development of new HIV non-nucleoside reverse transcriptase inhibitors offers the possibility of generating structures of increased potency. To this end, coupling of mefenamic acid (4) with 4-amino-acetophenone (6) in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine (DMAP) reagents afforded 4-(acetyphenyl)-2-((2,3-dimethylphenyl)amino)benzamide (7). Analogously, treatment of mefenamyl chloride (5) prepared from 4 with 6 under microwave irradiation (MWI) afforded 7. A new series of substituted chalconyl-incorporated amide derivatives of mefenamic acid 8–13 were synthesized from condensation of 7 with various substituted benzaldehydes via the Claisen–Schmidt reaction. Treatment of 8 and 11 with thiourea in a basic medium afforded the thiopyrimidine analogues 14 and 15, respectively. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 9 and 11 showed cytotoxicity values of 2.17 and 2.06 μm, respectively, against mock-infected MT-4 cells (C type adult T leukemia cells), which considered to be promising antileukemic agents.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
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