Abstract:

Thirteen new β-amino ketones were designed and synthesized directly through the Mannich reaction of sulfamethoxazole, 4-hydroxyacetophenone and aromatic aldehydes in good yields. The reaction selectively occurred at the α-position of the carbonyl group of 4-hydroxyacetophenone. Their chemical structures were confirmed by means of ¹H NMR, ¹³C NMR and MS. Biological activity tests showed that in the rage of low concentrations, these title compounds displayed a certain inhibitory activity against protein tyrosine phosphatase 1B(PTP1B) and α-glucosidase. Moreover, some could activate the peroxisome proliferatoractivated receptor response element(PPRE) moderately. The PPRE agonist activity of eight compounds was over 40%, among them compound 11 showed the highest activity(72.7%), which deserved further study.

Key words: α-Glucosidase, PTP1B, PPRE, hydroxyacetophenone, sulfamethoxazole, β-amino ketone