Synthesis and antimicrobial activity of cholic acid hydrazone analogues

Synthesis and antimicrobial activity of cholic acid analogues 4a–t are reported. The synthesis of 4a–t was accomplished from ethylcholate 2. The hydrazone moiety was introduced via coupling of the cholic acide hydrazide (3) with appropriately functionalized aldehyde utilizing acetic acid as a catalyst. Quiet of interest in relation to the synthesized hydrazones is the formation of two rotamers s-cis.E and s-trans.E. Most compounds showed stronger antimicrobial activity against Gram-positive bacteria than Cefaclor and Cefixime. Compounds 4d, 4i and 4j indicated 15-fold stronger antimicrobial activities against Enterobacter faecalis compared to Cefaclor and Cefixime. Some of the synthesized compounds (e.g. 4a, 4c, 4d, 4i, and 4l) reflected twofolds less activity against Escherichia coli relative to Cefixime.

Graphical abstractSynthesis and antimicrobial activity of cholic acid analogues are reported. Most compounds showed stronger antimicrobial activity against Gram-positive bacteria than Cefaclor and Cefixime. Some of the synthesized compounds indicated twofolds less activity against Gram-negative bacteria than Cefixime .Figure optionsDownload full-size imageDownload as PowerPoint slide