[Design of Novel Carboxamides of Eremomycin and Vancomycin with 4- or 3-Amino Methyl Phenyl Boric Acid and Their Investigation]

Antibiot Khimioter. 2015;60(9-10):7-11.
[Article in Russian]

Abstract

Amidation of the end carboxyl group of eremomycin and vancomycin by pinacolinic 4- or 3-amino methyl phenyl boron acids esters in the presence of the condensing reagent PyBOP resulted in formation of novel carboxamides of the antibiotics (IIIa-VIa). After elimination of the pinacolinic group under mild hydrolysis in weak acid aqueous medium there formed the respective derivatives with a residue of the nonprotected boric acid (III-VI). It was shown that the activity of the 4-substituted derivatives of the borole-containing eremomycin and vancomycin practically was the same as that of the initial antibiotics, while higher than that of the respective 3-substituted derivatives of the borole-containing derivatives against 8 strains of grampositive bacteria.

Publication types

  • English Abstract
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Boronic Acids / chemistry*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Glycopeptides / chemical synthesis*
  • Glycopeptides / chemistry
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Vancomycin / analogs & derivatives*
  • Vancomycin / chemical synthesis*
  • Vancomycin / chemistry

Substances

  • Anti-Bacterial Agents
  • Boronic Acids
  • Glycopeptides
  • eremomycin
  • Vancomycin