Bile acid amides derived from chiral amino alcohols: novel antimicrobials and antifungals

Cholic and deoxycholic acid amides 10– 17 have been synthesised from (1 R,2 R)-1-phenyl-2-amino-1,3-propanediol 2, (1 S,2 S)-1-phenyl-2-amino-1,3-propanediol 4, (1 R,2 R)-1- para-nitrophenyl-2-amino-1,3-propanediol 3, (1 S,2 S)-1- para-nitrophenyl-2-amino-1,3-propanediol 5. Amide 12 derived from N-succinimidyl ester 9 of deoxycholic acid and (1 R,2 R)-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 (1 S,2 S)-1- para-nitrophenyl-2-amino-1,3-propanediol 5, is found to be potent against various gram-positive bacteria. Synthesis and biological activity of eight new amides from bile acids and chiral aromatic amino alcohols are described.