Resumen de Synthesis and evaluation of 5-(6-methoxynaphthalen-2-yl)-1-aryl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one as potential antidiabetic agents

Han Hai Yan, Yan Ju Fang, Xu Jin, YE Fei, Fan Li, Zhou Guang-ming, Yang Da-cheng

• We wish to report a set of seventeen ketones bearing nabumetone and trifluoro- methylaniline(TFMA) moieties. Synthesized via direct Mannich reaction in a solution of ethanol- chloroform catalyzed by concentrated hydrochloric acid, the chemical structures of these compounds were characterized by IR, ¹H NMR, 13C NMR, ESI MS and HR MS. Studies on their antidiabetic activities revealed that all title compounds possessed moderate α-glucosidase inhibitory activities and protein tyrosine phosphatase 1B (PTP 1B) inhibitory activities. Among them, a few compounds also exhibit considerable peroxisome proliferator-activated receptor response element (PPRE) agonist activity, in particular the relative PPRE agonist activity of compounds 1r and 1l reached 54.02% and 57.60%, respectively. These results represent significant examples of new molecular type for antidiabetic agents that merit further evaluation.