Bile acid amides derived from chiral amino alcohols: novel antimicrobials and antifungals.
Cholic and deoxycholic acid amides 10-17 have been synthesised from (1R,2R)-1-phenyl-2-amino-1,3-propanediol 2, (1S,2S)-1-phenyl-2-amino-1,3-propanediol 4, (1R,2R)-1-para-nitrophenyl-2-amino-1,3-propanediol 3, (1S,2S)-1-para-nitrophenyl-2-amino-1,3-propanediol 5. Amide 12 derived from N-succinimidyl ester 9 of deoxycholic acid and (1R,2R)-1-phenyl-2-amino-1,3-propanediol 2, found to be active against Cryptococcus neoformans and the amide 17 obtained from N-succinimidyl ester 9 of deoxycholic acid and (1S,2S)-1-para-nitrophenyl-2-amino-1,3-propanediol 5, is found to be potent against various gram-positive bacteria.
Hazra
BrajaG
B
Organic Chemistry Synthesis Division, National Chemical Laboratory, Pune 411 008, India. hazra@ems.ncl.res.in
Pore
VandanaS
V
Dey
SanjeevKumar
S
Datta
Suchitra
S
Darokar
MahendraP
M
Saikia
Dharmendra
D
Khanuja
S P S
SP
Thakur
AnupP
A
D000577:Amides / Q000138:chemical synthesis / Q000494:pharmacology; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D019826:Cholic Acid / Q000138:chemical synthesis / Q000494:pharmacology; D003455:Cryptococcus neoformans / Q000187:drug effects; D003840:Deoxycholic Acid / Q000138:chemical synthesis / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000577:Amides; D000598:Amino Acids, Cyclic; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003840:Deoxycholic Acid; D019826:Cholic Acid