title: Synthesis and antibacterial activity of a novel class of 15-membered macrolide antibiotics, "11a-azalides".
abstract: An efficient method for the reconstruction of the 9-dihydroerythromycin A macrolactone skeleton has been established. The key steps are oxidative cleavage at the 11,12-position and reconstruction after insertion of an appropriate functionalized amino alcohol. Novel 15-membered macrolides, we named as "11a-azalides", were synthesized based on the above methodology and evaluated for their antibacterial activity. Among them, (13R)-benzyloxymethyl-11a-azalide showed the most potent Streptococcus pneumoniae activity, with improved activity against a representative erythromycin-resistant strain compared to clarithromycin (CAM).
authors.affiliation: Medicinal Research Laboratories , Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Kita-ku, Saitama-shi, Saitama 331-9530, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Sugimoto
authors.affiliation: Medicinal Research Laboratories , Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Kita-ku, Saitama-shi, Saitama 331-9530, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Tanikawa
keywords: 11a-azalide; Antibiotic; macrolide; novel scaffold; resistant-pathogen