Synthesis and biological activities of 4"-deoxy-4"-sulfonamido-oleandomycin derivatives

Autor: Bright, G M, English, A R, Nagel, A A, Retsema, J A, Sciavolino, F C
Zdroj: Antimicrobial Agents and Chemotherapy; January 1984, Vol. 25 Issue: 1 p113-117, 5p
Abstrakt: Chemical modification of the macrolide antibiotic oleandomycin (C-1) is described. Reductive amination of 11-acetyl-4"-deoxy-4"-oxo-oleandomycin (C-6) with ammonium acetate provides amino-oleandomycin derivative C-7 in which the 4"-amine is oriented in the axial configuration. The structure-activity relationship of a series of 4"-sulfonamide analogs prepared from amino-oleandomycin derivative C-7 is discussed. Noteworthy is the significant in vitro potency enhancement of the para-chlorobenzenesulfonamide analog C-12 over that of the parent oleandomycin. The absolute configuration of the 4"-amino-oleandomycin derivative C-7 was established through X-ray analysis of the para-iodobenzenesulfonamide analog C-14.
Databáze: Supplemental Index