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Selective protection of ribostamycin by cyclic carbamates

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

  1. Department of Chemical Biology, School of Pharmaceutical Sciences,
    State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, China
  • Received:2007-05-12 Revised:2007-11-10 Online:2007-12-15 Published:2007-12-15
  • Contact: Zhong-Jun Li*, Jing-Rong Cui*

Abstract:

Aim To develop a novel selective protection strategy for the synthesis of ribostamycin cyclic carbamate derivatives. Methods Ribostamycin protected by carbobenzoxy group was treated with NaH, to give different protected intermediates under respective controllable cyclization reaction conditions. New ribostamycin derivative was obtained after the cleavage of carbobenzoxy groups. Result The novel selective protection of ribostamycin was achieved by the synthesis of protected intermediates. New ribostamycin derivative was obtained, but showed no expected antibacterial activity. Conclusion Several ribostamycin cyclic carbamate derivatives were obtained by novel selective protection strategy, which shows the practicability and convenience of the protection strategy. But these new ribostamycin derivatives containing cyclic carbamates structure may not be an ideal leading compound for antibiotic activity.

Key words: Aminoglycoside, Aminoglycoside, Ribostamycin, Ribostamycin, Cyclic carbamate, Cyclic carbamate, Selectivity, Selectivity, Derivatives, Derivatives

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