The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
3-Keto-11, 12-carbazate Derivatives of 6-O-Methylerythromycin A Synthesis and In Vitro Activity
GEORGE GRIESGRABERYAT SUN ORDANIEL T. W. CHUANGELA M. NILIUSPAULINE M. JOHNSONROBERT K. FLAMMRODGER F. HENRYJACOB J. PLATTNER
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1996 Volume 49 Issue 5 Pages 465-477

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Abstract

The 11, 12-cyclic carbazate of 3-keto-6-O-methylerythromycin A (4) was prepared. This compound shows in vitro antibacterial activity comparable to erythromycin A (1) against erythromycin-susceptible organisms and increased activity against some erythromycin-resistant organisms. Using 4 as a lead, a series of analogues was prepared by acylation or alkylation of the carbazate nitrogen. Several of the N-alkylated derivatives showed dramatically improved antibacterial activity against both susceptible and resistant organisms as compared to erythromycin A.

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