European Journal of Medicinal Chemistry 2010-06-01

Synthesis and antimicrobial activity of cholic acid hydrazone analogues.

Anas J M Rasras, Taleb H Al-Tel, Amal F Al-Aboudi, Raed A Al-Qawasmeh, Anas J.M. Rasras, Taleb H. Al-Tel, Amal F. Al-Aboudi, Raed A. Al-Qawasmeh

Index: Eur. J. Med. Chem. 45 , 2307, (2010)

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Abstract

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 acid 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 two-folds less activity against Escherichia coli relative to Cefixime.Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.