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Molecules 2012, 17(1), 1025-1038; doi:10.3390/molecules17011025

Synthesis and Preliminary Antimicrobial Activities of New Arylideneamino-1,3,4-thiadiazole-(thio/dithio)-acetamido Cephalosporanic Acids

Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Bab-Al-muadham P.O. Box 14026, 10047, Baghdad, Iraq
Received: 9 October 2011 / Revised: 27 December 2011 / Accepted: 4 January 2012 / Published: 19 January 2012
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Abstract

New derivatives of 7-aminocephalosporanic acid 18 were synthesized by acylation of the 7-amino group of the cephem nucleus with various arylidinimino-1,3,4-thiadiazole-thio(or dithio)-acetic acid intermediates 3ad and 5ad, respectively, so the acyl side chains of these new cephalosporins contained a sulfide or disulfide bond. This unique combination of a Schiff base with the sulfide or disulfide bonds in the acyl side chain afforded new cephalosporins of reasonable potencies, some of which were found to possess moderate activities against the tested microorganisms. Their chemical structures were characterized by ¹H-NMR, IR spectroscopy and elemental microanalysis. Preliminary in vitro antimicrobial activities of the prepared cephalosporins were investigated using a panel of selected microorganisms. Results indicated that the newly synthesized cephalosporins containing disulfide bonds (compounds 58) exhibited better activities against Staphylococcus aureus and Escherichia coli. The cephalosporins cross-linked by a sulfide bond (compounds 14) showed a slight change in antimicrobial activities when compared with that of the reference cephalosporin (cephalexin).
Keywords: cephalosporins; 1,3,4-thiadiazole; antimicrobial activity; Schiff bases; disulfide bond cephalosporins; 1,3,4-thiadiazole; antimicrobial activity; Schiff bases; disulfide bond
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MDPI and ACS Style

Alwan, S.M. Synthesis and Preliminary Antimicrobial Activities of New Arylideneamino-1,3,4-thiadiazole-(thio/dithio)-acetamido Cephalosporanic Acids. Molecules 2012, 17, 1025-1038.

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