Volume 8, Number 4 (12-2009)                   JRUMS 2009, 8(4): 253-262 | Back to browse issues page


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Moshafi M, Safavi S, Foroumadi A. Synthesis and In vitro Antibacterial Activity of N-[5-(5-nitroaryl)-1,3,4-Thiadiazol-2-yl] Piperazinyl Quinolones. JRUMS. 2009; 8 (4) :253-262
URL: http://journal.rums.ac.ir/article-1-654-en.html

Abstract:   (15790 Views)

  M.H. Moshafi [1] , S.M. Safavi [2] , A. Foroumadi [3]

 

  Received: 23/02/09 Sent for Revision: 25/07/09 Received Revised Manuscript: 08/10/09 Accepted: 26/10/09

 

  Background and Objectives: Because resistance to antimicrobial drugs is widespread, recognition of new antimicrobial and understanding of their mechanisms are vital. The quinolones have a broad antibacterial spectrum of activity against Gram-positive, Gram-negative and mycobacterial pathogens such as anaerobes. In the present study, the synthesis and antibacterial activity of a new series of N-piperazinyl quinolones containing 5-(nitroaryl)-1, 3, 4-thiadiazole-2-yl moiety have been studied.

  Materials and Methods: In this laboratory study, the reaction of 1-cyclopropyl-6 fluoro-8 methoxy-4-oxo-7- (piperazin-1-yl)-1, 4- dihydroquinoline-3- carboxylic acid (compound 3), with 2-chloro-5-(nitroaryl)-1,3,4-thiadiazol (compounds 9a-f), in DMF in the presence of NaHCO3 at 85-90oC, gave final compounds 1- cyclopropyl- 6fluoro-7-[4-[5-(nitroaryl)-1,3, 4-thiadiazol-2yl], piperazin-1-yl] -8- methoxy-4-oxo-quinoline-3- carboxylic acid (8a-f). compounds 8a-f, were tested in vitro by the conventional agar dilution method against a panel of microorganisms including stophylococcus aureus, Escherichia coli, salmonella typhi, shigella flexneri, klebsiella pneumonia, serratia marcescens and pseudomonas aeruginosa.

  Results: Among synthesized compound, nitrofuran analog 8b exhibited more potent inhibitory activity against Gram-positive bacteria including B. subtilis, S. epidermidis, E. feacalis, M. luteus, in respect to other synthesized compounds and reference drug gatifloxacin.

  Conclusion: Introduction of the bulky group of [5-(5-nitroaryl)-1,3,4-thiadiazol-2-yl] could dramatically impact the antibacterial activity of the parent quinolone, and among the nitroaryl groups, 5-nitrofuryl analogue showed the most potent antibacterial activity against the tested microorganisms .

  Key words: Quinolones, Nitroaromatic Compounds, 1,3,4-Thiadiazole, Antibacterial Activity

 

  Funding: This research was funded by Kerman University of Medical Sciences.

  Conflict of Interest : None declared.



 

  [1] - Associate Prof., Dept. of Microbiology, Faculty of Pharmacy, University of Medical Sciences, Kerman, Iran

  [2] - Master Science, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

  [3] - Prof., Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

  ( Corresponding Author) Tel: (021) 66954708, Fax: (021) 66461178, E-mail: aforoumadi@yahoo.com

Full-Text [PDF 604 kb]   (1268 Downloads)    
Type of Study: Applicable | Subject: Microbiology
Received: 2010/01/6

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