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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (11): 1420-1426. 上一篇    下一篇

研究论文

N-(溴代-2-吡咯甲酰基)氨基酸甲酯的合成

曾向潮*，徐石海，李毅群，刘珀润，李玉霞   

  1. (暨南大学化学系 广州 510632 )
  • 收稿日期:2004-04-29 修回日期:2005-06-01 发布日期:2005-10-30
  • 通讯作者: 曾向潮

Synthesis of N-(Methoxycarbonylalkyl)bromopyrrole-2-carboamides

ZENG Xiang-Chao*,XU Shi-Hai,LI Yi-Qun,LIU Po-Run,LI Yu-Xia   

  1. (Department of Chemistry, Jinan University, Guangzhou 510632)
  • Received:2004-04-29 Revised:2005-06-01 Published:2005-10-30
  • Contact: ZENG Xiang-Chao

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1525

被引次数

1

在室温条件下, 2-三氯乙酰基吡咯经溴代反应, 再与氨基酸甲酯反应得到一系列N-(溴代-2-吡咯甲酰基)氨基酸甲酯, 收率为64.8%～92.2%. 通过元素分析, 1H NMR, IR和MS对产物结构进行了表征, 培养了N-(1-甲基-4,5-二溴-2-吡咯甲酰基)甘氨酸甲酯的单晶并进行单晶X射线衍射分析. 初步活性试验表明, 目标产物对金黄色葡萄球菌、粪链球菌等五种细菌有一定的抑制作用.

关键词: N-(溴代-2-吡咯甲酰基)氨基酸甲酯, 抑菌活性, 酰基化反应, 溴化反应, 合成

A series of N-(methoxycarbonylalkyl)bromopyrrole-2-carboamides were synthesized by acylation of amino acid methyl esters with bromo-2-trichloroacetylpyrroles at room temperature in 64.8%～92.2% yields. The structures of products were determined on the basis of 1H NMR, IR, MS spectra and elemental analyses. One of these products was analyzed by single crystal X-ray diffraction. Preliminary antibiotic tests showed that some target compounds inhibit the five bacteria such as Staphylococcus aureus and Streptococcus faecalis.

Key words: bromization, synthesis, antibiotic activity, acylation, N-(methoxycarbonylalkyl)bromopyrrole-2-carboamide