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

Authors Shan LX, Sun PH, Guo BQ, Xu XJ, Li ZQ, Sun JZ, Zhou SF, Chen WM

Received 7 April 2014

Accepted for publication 21 May 2014

Published 24 September 2014 Volume 2014:8 Pages 1515—1525

DOI https://doi.org/10.2147/DDDT.S65673

Checked for plagiarism Yes

Review by Single-blind

Peer reviewer comments 3

Ling-Xing Shan,1 Ping-Hua Sun,1,2 Bao-Qin Guo,1 Xing-Jun Xu,1 Zhi-Qiang Li,1 Jia-Zhi Sun,2 Shu-Feng Zhou,2 Wei-Min Chen1

1Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, People's Republic of China; 2College of Pharmacy, University of South Florida, Tampa, FL, USA

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

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