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有机化学 ›› 2009, Vol. 29 ›› Issue (11): 1790-1798. 上一篇    下一篇

研究论文

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   

  1. (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, Xuemeia     Yan, Jufangb      Zhang, Yingxiaa        Zhang, Weiyub       Su, Xiaoyana      Chen, Xinb       Zhou, Zuwena       Yang, Dacheng*,a   

  1. (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

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为了寻求新颖的抗糖尿病药物, 我们将芳香醛、对溴苯乙酮和磺胺嘧啶通过一步反应直接合成了16个未见报道的含有磺胺嘧啶结构的β-氨基酮化合物, 制备方法简便、反应条件温和, 收率为10.0%～80.1%. 所制备的化合物通过1H NMR, 13C NMR, MS和HRMS进行结构表征与确证. 对这些化合物进行α-葡萄糖苷酶抑制活性初步检测, 结果表明部分化合物在低浓度范围(8.1～9.3 nmol•mL－1)具有一定的α-葡萄糖苷酶抑制活性.

关键词: 磺胺嘧啶, Mannich碱, α-葡萄糖苷酶抑制剂, 糖尿病, β-氨基酮

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