Design, synthesis and antibacterial activity of a novel alkylide: 3-O-(3-aryl-propenyl)clarithromycin derivatives.
A series of novel 3-O-(3-aryl-propenyl)clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. Regioselective allylation at 3-OH was efficiently achieved in the presence of 9-oxime ether, compared with 9-keto. Most of the side chains were identified as the 3-O-(3-aryl-Z-prop-1-enyl) group, not the expected 3-O-(3-aryl-E-prop-2-enyl) group. Some derivatives of this series showed improved activities against erythromycin-resistant Staphylococcus aureus and Staphylococcus pneumoniae compared with the reference compound, clarithromycin, but weaker activities against susceptible strains.
Liang
Jian-Hua
JH
School of Life Science, Beijing Institute of Technology, Beijing, China. ljhbit@bit.edu.cn
Wang
Yue-Ying
YY
Zhu
Dan-Yang
DY
Dong
Li-Jing
LJ
An
Mao-Mao
MM
Wang
Rui
R
Yao
Guo-Wei
GW
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D017291:Clarithromycin / Q000031:analogs & derivatives* / Q000494:pharmacology; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D017291:Clarithromycin