Document Report Card

ID: ALA1125014

Journal: J Med Chem

Title: Synthesis and structure-activity relationships of new 9-N-alkyl derivatives of 9(S)-erythromycylamine.

Authors: Kirst HA, Wind JA, Leeds JP, Willard KE, Debono M, Bonjouklian R, Greene JM, Sullivan KA, Paschal JW, Deeter JB.

Abstract: A series of new 9-N-alkyl derivatives of 9(S)-erythromycylamine has been synthesized by reductive alkylation of erythromycylamine with aliphatic aldehydes and sodium cyanoborohydride. Alternative syntheses employing hydrogenation methods have also been developed. These new 9-N-alkyl derivatives possess excellent antimicrobial activity in vitro and in vivo, especially when administered orally to treat experimental infections in mice. From structure-activity studies, 9-N-(1-propyl)erythromycylamine (LY281389) was selected as the most efficacious derivative. These methods have also been extended to the synthesis of some 9-N,N-dialkyl derivatives of erythromycylamine.

CiteXplore: 2231610

DOI: 10.1021/jm00173a028