Stereoselective synthesis and antimicrobial activity of steroidal C-20 tertiary alcohols with thiazole/pyridine side chain

Bapurao B Shingate; Braja G Hazra; Deepak B Salunke; Vandana S Pore; Fazal Shirazi; Mukund V Deshpande

doi:10.1016/j.ejmech.2011.05.032

Stereoselective synthesis and antimicrobial activity of steroidal C-20 tertiary alcohols with thiazole/pyridine side chain

Eur J Med Chem. 2011 Sep;46(9):3681-9. doi: 10.1016/j.ejmech.2011.05.032. Epub 2011 May 20.

Authors

Bapurao B Shingate¹, Braja G Hazra, Deepak B Salunke, Vandana S Pore, Fazal Shirazi, Mukund V Deshpande

Affiliation

¹ Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India. [email protected]

PMID: 21664730
DOI: 10.1016/j.ejmech.2011.05.032

Abstract

Stereoselective synthesis of novel steroidal C-20 tertiary alcohols with thiazole and pyridine side chain using Grignard reaction of steroidal ketones and thiazole/pyridine magnesium bromide have been realized. These molecules were evaluated in vitro for their antifungal and antibacterial activities. Most of the compounds exhibited significant antifungal and antibacterial activity against all the tested strains.

Publication types

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

MeSH terms

Alcohols / chemical synthesis*
Alcohols / chemistry
Alcohols / pharmacology*
Anti-Infective Agents / chemical synthesis*
Anti-Infective Agents / chemistry
Anti-Infective Agents / pharmacology*
Bacteria / drug effects
Chromatography, Liquid
Fungi / drug effects
Magnetic Resonance Spectroscopy
Mass Spectrometry
Microbial Sensitivity Tests
Pyridines / chemistry*
Stereoisomerism
Thiazoles / chemistry*

Substances

Alcohols
Anti-Infective Agents
Pyridines
Thiazoles
pyridine