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Synthesis of kanamycin A derivatives by regioselective masking drug resistant enzymes targeting hydroxyl groups

Ying Chen, Xiang-Bao Meng, Gui-Hui Chen, Pan Pan, Zhong-Jun Li*   

  1. The State Key Laboratory of Natural and Biomimetic drugs;
    Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China
  • Received:2008-01-22 Revised:2008-05-10 Online:2008-06-15 Published:2008-06-15
  • Contact: Zhong-Jun Li*

Abstract:

The 3'-OH, 4'-OH and 2''-OH of kanamycin A were modified in search of new aminoglycosides to overcome resistant enzymes, ANTs and APHs. The key intermediate was a dibenzylidene-protected derivative of kanamycin A. The aimed sites were masked by benzyl, methyl and allyl groups. Multi-step reactions gave the desired aminoglycoside derivatives but showed less antibiotic activity than kanamycin A.

Key words: Aminoglycoisdes, Aminoglycoisdes, Kanamycin A derivatives, Kanamycin A derivatives, Resistant enzyme, Resistant enzyme, Regioselectivity, Regioselectivity, ,

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