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Journal of the Chilean Chemical Society

versão On-line ISSN 0717-9707

Resumo

YAN, HAN HAI et al. SYNTHESIS AND EVALUATION OF 5-(6-METHOXYNAPHTHALEN-2-YL)-1-ARYL-1-(4-(TRIFLUOROMETHYL)PHENYLAMINO)PENTAN-3-ONE AS POTENTIAL ANTIDIABETIC AGENTS. J. Chil. Chem. Soc. [online]. 2011, vol.56, n.4, pp.930-934. ISSN 0717-9707.  http://dx.doi.org/10.4067/S0717-97072011000400023.

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.

Palavras-chave : Diabetes Mellitus; PPRE; α-Glucosidase; PTP 1B; ketones; Mannich base.

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