Chemical Transformations of Antibiotic X-537A and Their Effect on Antibacterial Activity

John W. Westley; Eugene P. Oliveto; Julius Berger; Ralph H. Evans; Richard Glass; Arthur Stempel; Voldemar Toome; Thomas Williams

doi:10.1021/jm00262a020

Chemical Transformations of Antibiotic X-537A and Their Effect on Antibacterial Activity

John W. Westley, Eugene P. Oliveto, Julius Berger, Ralph H. Evans, Richard Glass, Arthur Stempel, Voldemar Toome, Thomas Williams

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

Abstract

A number of derivatives of the polyether antibiotic X-537A have been tested in vitro vs. Bacillus E and Bacillus TA and the results clearly indicate that all the oxygen functions involved in ligand formation with cations and intramolecular hydrogen bonding (as revealed by X-ray analysis) contribute to the biological activity of the antibiotic. In addition, a number of derivatives at the C-5 position of the aromatic chromo-phore exhibited a qualitative correlation between their partition coefficients (octanol-water) and in vitro activity.

Original language	English (US)
Pages (from-to)	397-403
Number of pages	7
Journal	Journal of Medicinal Chemistry
Volume	16
Issue number	4
DOIs	https://doi.org/10.1021/jm00262a020
State	Published - Apr 1 1973
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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abstract = "A number of derivatives of the polyether antibiotic X-537A have been tested in vitro vs. Bacillus E and Bacillus TA and the results clearly indicate that all the oxygen functions involved in ligand formation with cations and intramolecular hydrogen bonding (as revealed by X-ray analysis) contribute to the biological activity of the antibiotic. In addition, a number of derivatives at the C-5 position of the aromatic chromo-phore exhibited a qualitative correlation between their partition coefficients (octanol-water) and in vitro activity.",

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AU - Westley, John W.

AU - Oliveto, Eugene P.

AU - Berger, Julius

AU - Evans, Ralph H.

AU - Glass, Richard

AU - Stempel, Arthur

AU - Toome, Voldemar

AU - Williams, Thomas

PY - 1973/4/1

Y1 - 1973/4/1

N2 - A number of derivatives of the polyether antibiotic X-537A have been tested in vitro vs. Bacillus E and Bacillus TA and the results clearly indicate that all the oxygen functions involved in ligand formation with cations and intramolecular hydrogen bonding (as revealed by X-ray analysis) contribute to the biological activity of the antibiotic. In addition, a number of derivatives at the C-5 position of the aromatic chromo-phore exhibited a qualitative correlation between their partition coefficients (octanol-water) and in vitro activity.

AB - A number of derivatives of the polyether antibiotic X-537A have been tested in vitro vs. Bacillus E and Bacillus TA and the results clearly indicate that all the oxygen functions involved in ligand formation with cations and intramolecular hydrogen bonding (as revealed by X-ray analysis) contribute to the biological activity of the antibiotic. In addition, a number of derivatives at the C-5 position of the aromatic chromo-phore exhibited a qualitative correlation between their partition coefficients (octanol-water) and in vitro activity.

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Chemical Transformations of Antibiotic X-537A and Their Effect on Antibacterial Activity

Abstract

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