Synthesis and antibacterial activities of 6-O-methylerythromycin A 9-O-(3-aryl-2-propenyl) oxime ketolide, 2,3-enol ether, and alkylide analogues.
A facile and efficient route was presented to achieve 3-keto-clarithromycin 9-O-(3-aryl-E-2-propenyl) oxime derivatives 8, 2,3-dehydro-3-O-allyl-clarithromycin 9-O-(3-aryl-E-2-propenyl) oxime derivatives 11, and 3-O-allyl-clarithromycin 9-O-(3-aryl-E-2-propenyl) oxime derivatives 12. Among them, compound 8, particularly 8d (Ar = 6-quinolyl), exhibited improved antibacterial activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae, and greatly enhanced activities against the resistant strains encoded by erm and mef genes, as compared to clarithromycin and azithromycin.
Liang
Jian-Hua
JH
School of Life Science, Beijing Institute of Technology, Beijing 100081, China. ljhbit@bit.edu.cn
Dong
Li-Jing
LJ
Wang
He
H
An
Kun
K
Li
Xiao-Li
XL
Yang
Li
L
Yao
Guo-Wei
GW
Xu
Ying-Chun
YC
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D024881:Drug Resistance, Bacterial / Q000187:drug effects / Q000235:genetics; D004987:Ethers / Q000737:chemistry*; D048628:Ketolides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects / Q000235:genetics; D013296:Streptococcus pneumoniae / Q000187:drug effects / Q000235:genetics
D000900:Anti-Bacterial Agents; D004987:Ethers; D048628:Ketolides