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. 1984 Jan;25(1):113-7.
doi: 10.1128/AAC.25.1.113.

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

G M Bright, A R English, A A Nagel, J A Retsema, F C Sciavolino

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

G M Bright et al. Antimicrob Agents Chemother. 1984 Jan.

Abstract

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.

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