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

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.

Graphical abstractStereoselective synthesis and antimicrobial activity 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.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Homologation of 16-dehydropregnenolone acetate by Grignard reaction. ► Exclusive formation of steroidal C-20 tertiary alcohols with 100% stereoselectivity. ► In vitro antimicrobial evaluation of the synthesized alcohols. ► Most of the compounds exhibited significant activity. ► Methodology may be useful for the synthesis of C-20 tert-alcohols with heteryl side chains.