Synthesis of a series of guanidine substituted derivatives of aminoglycosides

doi:10.5246/jcps.2011.02.016

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Synthesis of a series of guanidine substituted derivatives of aminoglycosides

Bo Peng, Gui-Hui Chen, Pan Pan, Xiang-Bao Meng, He-Qing Huang^*, Shu-Chun Li, Zhong-Jun Li^*

State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2010-12-13 Revised:2011-01-20 Online:2011-03-15 Published:2011-03-15
Contact: He-Qing Huang*, Zhong-Jun Li*

Abstract

Abstract:

A novel method to prepare guanidine substituted aminoglycoside derivatives was developed. Free guanidine reacted with Cbz-protected aminoglycosides to produce guanidinylcarbonyl substituted derivatives. A methoxycarbonyl-protected intermediate was isolated, and the mechanism of guanidinylcarbonyl modification was proposed. With this method, six per- or part- guanidylcarbonyl substituted aminoglycosides were successfully obtained in good yields. Their in vitro antibacterial activities were essayed.

Key words: Aminoglycoside, Cbz, Substituted, Guanidine, Antibacterial activities

CLC Number:

R916

Supporting:

Bo Peng, Gui-Hui Chen, Pan Pan, Xiang-Bao Meng, He-Qing Huang^*, Shu-Chun Li, Zhong-Jun Li^* . Synthesis of a series of guanidine substituted derivatives of aminoglycosides [J]. , DOI: 10.5246/jcps.2011.02.016.

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Synthesis of a series of guanidine substituted derivatives of aminoglycosides

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