Synthesis and Preliminary Study on α-Glucosidase Inhibitory Activity of 4-[3-(4-Bromophenyl)-3-oxo-1-arylpropylamino]-N-(pyrimidin-2-yl)benzenesulfonamide

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (11): 1790-1798. Previous Articles Next Articles

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4-[3-(4-溴苯基)-3-氧代-1-芳基丙氨基]-N-(嘧啶-2-基)苯磺酰胺的合成及其α-葡萄糖苷酶抑制活性初步研究

唐雪梅^a 晏菊芳^b 张映霞^a 张蔚瑜^b 苏小燕^a 陈欣^b 周祖文^a 杨大成^*,a

(a西南大学化学化工学院重庆 400715) (b成都地奥制药集团有限公司药物筛选中心成都 610041)

收稿日期:2009-03-27 修回日期:2009-05-26 发布日期:2009-06-16
通讯作者: 杨大成 E-mail:hxydc@swu.edu.cn

Synthesis and Preliminary Study on α-Glucosidase Inhibitory Activity of 4-[3-(4-Bromophenyl)-3-oxo-1-arylpropylamino]-N-(pyrimidin-2-yl)benzenesulfonamide

Tang, Xuemei^a Yan, Jufang^b Zhang, Yingxia^a Zhang, Weiyu^b Su, Xiaoyan^a Chen, Xin^b Zhou, Zuwen^a Yang, Dacheng^*,a

(^a School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715) (^b Drug Screening Center, Chengdu Di Ao Pharmaceutical Group Limited Company, Chengdu 610041)

Received:2009-03-27 Revised:2009-05-26 Published:2009-06-16

Abstract

To explore novel antidiabetic drugs with high efficacy and low toxicity, sixteen new β-amino ketones containing a sulfadiazine moiety have been synthesized through Mannich reaction of sulfadiazine with p-bromoacetophenone and some aromatic aldehydes in the yields of 10.0%～80.1%. Their chemical structures have been confirmed by IR, 1H NMR, 13C NMR, ESI-MS and HRMS techniques. The preliminary α-glucosidase inhibitory activity bioassay of these compounds indicated that some compounds displayed α-glucosidase inhibitory activity in the low concentration range of 8.1～9.3 nmol•mL－1.

Key words: sulfadiazine, Mannich base, α-glucosidase inhibitor, diabetes mellitus, β-amino ketone

Cite this article

TANG Xue-Mei, YAN Ju-Fang, ZHANG Yang-Xia, ZHANG Wei-Yu, SU Xiao-Yan, CHEN Xin, ZHOU Jie-Wen, YANG Da-Cheng. Synthesis and Preliminary Study on α-Glucosidase Inhibitory Activity of 4-[3-(4-Bromophenyl)-3-oxo-1-arylpropylamino]-N-(pyrimidin-2-yl)benzenesulfonamide[J]. Chin. J. Org. Chem., 2009, 29(11): 1790-1798.

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4-[3-(4-溴苯基)-3-氧代-1-芳基丙氨基]-N-(嘧啶-2-基)苯磺酰胺的合成及其α-葡萄糖苷酶抑制活性初步研究

Synthesis and Preliminary Study on α-Glucosidase Inhibitory Activity of 4-[3-(4-Bromophenyl)-3-oxo-1-arylpropylamino]-N-(pyrimidin-2-yl)benzenesulfonamide

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