Synthesis and biological activities of 4"-deoxy-4"-sulfonamido-oleandomycin derivatives.
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.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D051379:Mice; D009827:Oleandomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013203:Staphylococcal Infections / Q000517:prevention & control*; D013329:Structure-Activity Relationship
D009827:Oleandomycin