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Citation: ZHANG Ying-Xia, YAN Ju-Fang, FAN Li, ZHANG Wei-Yu, SU Xiao-Yan, CHEN Xin, TANG Xue-Mei, ZHOU Zu-Wen, YANG Da-Cheng. Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(3-(4-Hydroxyphenyl)-3-oxo-1-arylpropylamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide[J]. Chinese Journal of Applied Chemistry, ;2010, 27(9): 1026-1031. doi: 10.3724/SP.J.1095.2010.90506 shu

Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(3-(4-Hydroxyphenyl)-3-oxo-1-arylpropylamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide

a. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715;
b. Drug Screening Center, Chengdu Di Ao Pharmaceutical Group Co. Ltd, Chengdu

Received Date: 27 July 2009
Revised Date: 13 March 2010

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.
- α-glucosidase,
- protein tyrosine phosphatase 1B,
- peroxisome proliferator-activated receptor response element,
- hydroxyacetophenone,
- sulfamethoxazole,
- β-amino ketone,
- Mannich reaction
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