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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 μ m , respectively, against mock-infected MT-4 cells (C type adult T leukemia cells), which considered to be promising antileukemic agents.

zeitschrift für naturforschung b

New chalcones and thiopyrimidine analogues derived from mefenamic acid: microwave-assisted synthesis, anti-HIV activity and cytotoxicity as antileukemic agents