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

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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

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

doi

10.1021/jm00173a028

subject

Has Abstract,Author List Incomplete

pub_date

1990-11-01 00:00:00

pages

3086-94

issue

11

eissn

0022-2623

issn

1520-4804

journal_volume

33

pub_type

杂志文章

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