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

Bioorg Med Chem Lett. 2004 Feb 9;14(3):773-7. doi: 10.1016/j.bmcl.2003.11.018.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides* / chemical synthesis
  • Amides* / pharmacology
  • Amino Acids, Cyclic* / chemical synthesis
  • Amino Acids, Cyclic* / pharmacology
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology
  • Cholic Acid* / chemical synthesis
  • Cholic Acid* / pharmacology
  • Cryptococcus neoformans / drug effects
  • Deoxycholic Acid* / chemical synthesis
  • Deoxycholic Acid* / pharmacology
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Amides
  • Amino Acids, Cyclic
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Deoxycholic Acid
  • Cholic Acid