Design and synthesis of bile acid-based amino sterols as antimicrobial agents.
New bile acid-based amino sterols were synthesized in good yields from C-3beta-oxiranes as key intermediates. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. These compounds showed better antibacterial activity as compared to antifungal activity. Compounds 21 and 22 showed comparable antibacterial activity to gentamicin against Staphylococcus aureus with IC50 values of 5.14 and 4.46 microg/mL. This is the first report for the synthesis of C-3beta-oxiranes on the steroids having A/B cis ring junction and these oxiranes have been used for the synthesis of amino sterols 17, 18, 21, and 22.
Aher
Nilkanth G
NG
Organic Chemistry Division, National Chemical Laboratory, Pune 411 008, India.
Pore
Vandana S
VS
Mishra
Nripendra N
NN
Shukla
Praveen K
PK
Gonnade
Rajesh G
RG
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001647:Bile Acids and Salts / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D013261:Sterols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000588:Amines; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D001647:Bile Acids and Salts; D013261:Sterols