Sordarin Oxazepine Derivatives as Potent Antifungal Agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 12; no. 19; pp. 2757 - 2760
• Main Authors: Serrano-Wu, Michael H., St. Laurent, Denis R., Chen, Yijun, Huang, Stella, Lam, Kin-Ray, Matson, James A., Mazzucco, Charles E., Stickle, Terry M., Tully, Thomas P., Wong, Henry S., Vyas, Dolatrai M., Balasubramanian, Balu N.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 07.10.2002; Elsevier
• Subjects: Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Biological and medical sciences; Candida albicans - drug effects; Candida glabrata - drug effects; Cryptococcus neoformans - drug effects; Fungi - drug effects; Hydrogen Bonding; Indenes; Medical sciences; Microbial Sensitivity Tests; Oxazepines - chemical synthesis; Oxazepines - pharmacology; Pharmacology. Drug treatments; Structure-Activity Relationship; Candida albicans; Terpenoid; Aldehydoacid; Cryptococcus neoformans; Candida glabrata; In vitro; Fungi; Antifungal agent; Structure activity relation; Chlorine Organic compounds; Oxazepine derivatives; Diterpene; Fungi Imperfecti; Chemical synthesis; Thallophyta; Seven membered ring; Oxygen nitrogen heterocycle
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(02)00529-2

The synthesis and biological activity of sordarin oxazepine derivatives are described. The key step features a regioselective oxidation of an unprotected triol followed by double reductive amination to afford the ring-closed products. The spectrum of antifungal activity for these novel derivatives includes coverage of Candida albicans, Candida glabrata, and Cryptococcus neoformans. The synthesis and antifungal activity of sordarin oxazepine derivatives are described.