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甘草次酸3位氨基酸衍生物的合成及其抑菌活性

王军1*,2,胡小丽2,文伟河2,杨雷雷2,朱玉亮2   

  1. (1.江苏警官学院公安科技系 南京 210012；2.南京工业大学生物与制药工程学院 南京 210009)
  • 收稿日期:2011-08-25 修回日期:2011-11-27 出版日期:2012-08-10 发布日期:2012-08-10
  • 通讯作者: 王军，副教授; Tel/Fax:025-83587330; E-mail:kwangjun@163.com; 研究方向：药物改性

Synthesis and Activity of 3-Amino Acid Derivatives of Glycyrrhetinic Acid

WANG Jun1*，2, HU Xiaoli2, WEN Weihe2, YANG Leilei2, ZHU Yuliang2   

  1. (1.Department of Forensic Science,Jiangsu Police Institute,Nanjing 210012,China;
    2.College of Biotechnology and Pharmaceutical Engineering,Nanjing University of Technology,Nanjing 210009,China)
  • Received:2011-08-25 Revised:2011-11-27 Published:2012-08-10 Online:2012-08-10
  • Contact: wang jun

PDF

926

被引次数

11

摘要： 以甘草次酸(1)为原料，将其11位羰基还原、30位羧基酯化得11-脱氧甘草次酸-30-乙酯(3)。 再以四氢呋喃为溶剂，N,N′-二环己基碳二亚胺(DCC)/4-二甲基氨基吡啶(DMAP)为偶合剂，选用Fmoc保护氨基酸对11-脱氧甘草次酸-30-乙酯的3位羟基进行酯化，得到11-脱氧甘草次酸-30-乙酯-3位氨基酸酯衍生物（4a~4d）。 化合物4a~4d在V(CHCl2)∶V(Et2NH)=1∶1溶液中脱去Fmoc保护基得到最终产物（5a~5d），产率80%~87%。 化合物5a~5d用1H NMR、EI-MS进行了表征。 活性实验结果表明，化合物5a~5d对在高浓度二甲基甲酰胺下生长的枯草芽孢杆菌、大肠杆菌和酵母菌具有保护作用。

关键词: 甘草次酸, Fmoc保护氨基酸, 还原, 酯化, 脱保护

Abstract: In order to obtain more effective glycyrrhetinic derivatives, 3-amino acid derivatives were synthesized from glycyrrhetinic acid via deoxidation of the 11-carbonyl group, ethyl esterification of the 30-carboxylic group and esterification of 3-hydroxyl group using Fmoc-protected amino acids, which include methionine, threonine, valine and phenylalanine, by dicyclohexylcarbodiimide(DCC)/dimethylaminopyridine(DMAP) coupling method in tetrahydrofuran. The final products were obtained by removing Fmoc using V(CH2Cl2)∶V((C2H5)2NH)=1∶1 solvent mixture with 80%~87% yields and characterized by 1H NMR and MS. Preliminary pharmacological research showed that compounds 5a~5d could protect the growth of E col., Bacillus Subtilis and Yeast against high level of N,N-dimethylformamide.

Key words: Glycyrrhetinic, Fmoc protected amino acids, deoxidation, esterrification, deprotect

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