title: Synthesis and antibacterial activities of a novel alkylide: 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives.
abstract: A series of novel 3-O-(3-aryl-E-2-propenyl)clarithromycin derivatives 8 and 3-O-(3-aryl-2-propargyl)clarithromycin derivatives 11 were designed, synthesized, and evaluated for their in vitro antibacterial activities. Compared with 8c and 11c (Ar was 5-pyrimidyl), 3-O-(3-(5'-pyrimidyl)-Z-1-propenyl) counterpart 6c displayed 4- to 64-fold more potent activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae. Moreover, the activities of 6c, 8c, and 11c against erythromycin-resistant S. aureus and S. pneumoniae were in general 4-fold higher than those of the reference compound, clarithromycin and azithromycin.
authors.affiliation: School of Life Science, Beijing Institute of Technology, Beijing 100081, China. ljhbit@bit.edu.cn
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Liang
authors.forename: Yue-Ying
authors.initials: YY
authors.lastname: Wang
authors.forename: He
authors.initials: H
authors.lastname: Wang
authors.forename: Xiao-Li
authors.initials: XL
authors.lastname: Li
authors.forename: Kun
authors.initials: K
authors.lastname: An
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Xu
authors.forename: Guo-Wei
authors.initials: GW
authors.lastname: Yao
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017291:Clarithromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects; D013296:Streptococcus pneumoniae / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D017291:Clarithromycin