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 ^[1] ; YAN JU FANG ^[2] ; XU JIN ^[1] ; YE Fei ^[2] ; FAN LI ^[1] ; ZHOU GUANG-MING ^[1] ; YANG DA-CHENG ^[1]
  1. [1] Southwest University

     Southwest University

     China

     
  2. [2] Drug Screening Center Chengdu Di Ao Pharmaceutical Group
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 56, Nº. 4, 2011, págs. 930-934
• Idioma: inglés
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• Resumen

  • 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.