Synthesis and antibacterial activities of acylide derivatives bearing an aryl-tetrazolyl chain

Abstract

Seventeen acylides bearing an aryl-tetrazolyl alkyl-substituted side chain were synthesized, starting from clarithromycin, via several reactions including hydrolysis, acetylating, esterification, carbamylation, and Michael addition. The structures of all new compounds were confirmed by ¹H nuclear magnetic resonance spectroscopy, ¹³C nuclear magnetic resonance spectroscopy, and mass spectrometry. All these synthesized acylides were evaluated for in vitro antimicrobial activities against gram-positive pathogens (Staphylococcus aureus, Staphylococcus epidermidis) and gram-negative pathogens (Pseudomonas aeruginosa, Escherichia coli), using the broth microdilution method. Results showed that compounds 10e, 10f, 10g, 10 h, 10o have good antibacterial activities.

Keywords:

• acylide
• clarithromycin
• synthesis
• antibacterial activity

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No 81072554, 81373285) and by the 111 Project (No B13038).

Disclosure

The authors report no conflicts of interest in this work.