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 cata...

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Bibliographic Details
Published in:	European journal of medicinal chemistry Vol. 45; no. 6; pp. 2307 - 2313
Main Authors:	Rasras, Anas J.M., Al-Tel, Taleb H., Al-Aboudi, Amal F., Al-Qawasmeh, Raed A.
Format:	Journal Article
Language:	English
Published:	Kidlington Elsevier Masson SAS 01-06-2010 Elsevier
Subjects:	Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antimicrobial activity Bacteria - drug effects Bile acids Biological and medical sciences Cholic acid Cholic Acid - chemistry Cholic acid hydrazones General aspects Hydrazones - chemical synthesis Hydrazones - chemistry Hydrazones - pharmacology Medical sciences MIC values Pharmacology. Drug treatments Rotamers Antimicrobial activity Bile acids Rotamers Cholic acid Cholic acid hydrazones MIC values Organic hydrazide Steroid Cholane derivatives Escherichia coli In vitro Biological activity Antimicrobial agent Bile acid Bacteria Cefixime Chemical synthesis Enterobacteriaceae Halogen Organic compounds
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Summary:	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. Synthesis 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 [Display omitted] .
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0223-5234 1768-3254
DOI:	10.1016/j.ejmech.2010.02.006