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Kirst, H.A. et al.

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

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.[1]

References

Synthesis and structure-activity relationships of new 9-N-alkyl derivatives of 9(S)-erythromycylamine. Kirst, H.A., Wind, J.A., Leeds, J.P., Willard, K.E., Debono, M., Bonjouklian, R., Greene, J.M., Sullivan, K.A., Paschal, J.W., Deeter, J.B. J. Med. Chem. (1990) [Pubmed]

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