Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates

Bioorg Med Chem Lett. 2013 Aug 1;23(15):4315-8. doi: 10.1016/j.bmcl.2013.05.098. Epub 2013 Jun 7.

Abstract

A series of 3α-amino-5α-cholestane and 3α,7α-diamino-5α-cholestane derivatives containing imidazole and pyridine rings were synthesized by simple and effective reductive amination, and their in vitro activities against a range of Gram-positive and Gram-negative strains were evaluated. Most of the compound exhibited enhanced activity against MRSA pathogen. 3α,7α-Di(pyridylmethyl)amino-5α-cholestane 10 showed the highest potency in these series toward the Gram-positive bacteria, Staphylococcus epidermidis 887E, with the lowest MIC value of 1 μg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Cholestanes / chemistry*
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Imidazoles / chemistry*
  • Microbial Sensitivity Tests
  • Pyridines / chemistry*
  • Staphylococcus epidermidis / drug effects

Substances

  • Anti-Infective Agents
  • Cholestanes
  • Imidazoles
  • Pyridines
  • imidazole
  • pyridine