Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 138-144.DOI: 10.6023/cjoc1104084 Previous Articles     Next Articles



王军a,b, 文伟河b, 胡小丽b, 朱玉亮b   

  1. a 江苏警官学院公安科技系 南京 210012;
    b 南京工业大学生物与制药工程学院 南京 210009
  • 收稿日期:2011-04-08 修回日期:2011-08-05 发布日期:2012-01-28
  • 通讯作者: 王军

Synthesis and Activity of 11-Deoxoglycyrrhetinic Acid 3-Monodesmosides

Wang Juna,b, Wen Weiheb, Hu Xiaolib, Zhu Yuliangb   

  1. a Department of Forensic Science, Jiangsu Police Institute, Nanjing 210012;
    b College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009
  • Received:2011-04-08 Revised:2011-08-05 Published:2012-01-28
  • Contact: Wang Jun

Five 11-deoxoglycyrrhetinic acid 3-monodesmosides were synthesized and the bacteriostatic activities were studied. Before the glycosylation, benzoyl glycoyl trichloroacetimidates were synthesized as donors, then, 3-OH of acetyl 11-deoxoglycyrrhetinate was coupled as glycosyl-receptors with the donors through glycosylation method at the promotion of trimethylsilyl trifluoromethanesulphonate (TMSOTf) to afford 5 benzoyl glycosyl derivatives of acetyl 11-deoxoglycyrrhetinate 7a7e. Deprotection of the derivatives afforded acetyl 11-deoxoglycyrrhetinate 3-monodesmoside 8a8e. The structures all compounds were characterized by 1H NMR, MS and Ultimate analysis. The preliminary pharmacological research showed that compound 8a could protect the growth of E. col while 8e could protect the growth of Bacillus subtilis and yeast at high level of N,N-dimethylformamide (DMF).

Key words: acetyl 11-deoxoglycyrrhetinate, glycosylation, synthesis