Quaternary Alkylammonium Conjugates of Steroids: Synthesis, Molecular Structure, and Biological Studies

Molecules. 2015 Nov 23;20(11):20887-900. doi: 10.3390/molecules201119735.

Abstract

The methods of synthesis as well as physical, spectroscopic (¹H-NMR, 13C-NMR, and FT-IR, ESI-MS), and biological properties of quaternary and dimeric quaternary alkylammonium conjugates of steroids are presented. The results were contrasted with theoretical calculations (PM5 methods) and potential pharmacological properties (PASS). Alkylammonium sterols exhibit a broad spectrum of antimicrobial activity comparable to squalamine.

Keywords: PM5 calculations; bile acids; conjugates; prediction of activity spectra for substances (PASS); quaternary alkylammonium salt; squalamine; sterols.

Publication types

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

MeSH terms

  • Animals
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / pharmacology
  • Bile Acids and Salts / chemical synthesis
  • Bile Acids and Salts / pharmacology
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Quaternary Ammonium Compounds / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • Steroids / chemical synthesis
  • Steroids / chemistry*
  • Steroids / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • Bile Acids and Salts
  • Quaternary Ammonium Compounds
  • Steroids