title: Synthesis and antibacterial activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives.
abstract: An allyl group was attached to 3-keto function of ketolides in the presence of allyl bromide and KOtBu. Consequently, the Heck reaction of the resulting 2, 3-dehydro-3-O-allyl-10, 11-anhydroclarithromycin derivatives, in the presence of palladium (II) acetate and tri(o-tolyl)phosphine, afforded a 3-O-(3-aryl-E-prop-2-enyl) sidechain, not the previously reported 3-O-(3-aryl-Z-prop-1-enyl) sidechain. The results suggested that some steric factors in β-hydrogen elimination might regulate the isomerization. The activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives was low.
authors.affiliation: School of Life Science, Beijing Institute of Technology, Beijing, China. ljhbit@bit.edu.cn
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Liang
authors.forename: Li-Jing
authors.initials: LJ
authors.lastname: Dong
authors.forename: Yue-Ying
authors.initials: YY
authors.lastname: Wang
authors.forename: Guo-Wei
authors.initials: GW
authors.lastname: Yao
authors.forename: Mao-Mao
authors.initials: MM
authors.lastname: An
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D017291:Clarithromycin / Q000031:analogs & derivatives / Q000494:pharmacology*; D024881:Drug Resistance, Bacterial; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D017291:Clarithromycin