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Synthesis, Characterization and Biological Screening of Various S-substituted Derivatives of 5-(3-Nitrophenyl)-1,3,4-Oxadiazole-2-thiol

Author(s): Aziz-ur-Rehman | K. Nafeesa | M. A. Abbasi | H. Kashfa | S. Rasool | I. Ahmad | S. Arshad

Journal: Pakistan Journal of Chemistry
ISSN 2220-2625

Volume: 3;
Issue: 2;
Start page: 56;
Date: 2013;
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Keywords: 3-Nitrobenzoic acid | Oxadiazole | Antibacterial potential | 1H-NMR and EI-MS.

In the presented research work, a series of S-substituted derivatives of 5-(3-nitrophenyl)-1,3,4-Oxadiazole-2-thiol was synthesizedfrom 3-nitrobenzoic acid. The synthesis was carried out by converting 3-nitrobenzoic acid correspondingly into ester, hydrazideand 5-(3-nitrophenyl)-1,3,4-Oxadiazole-2-thiol (4). Finally, the S-substituted derivatives (6a-m) were brought about by reacting 5-(3-nitrophenyl)-1,3,4-Oxadiazole-2-thiol with different electrophiles (5a-m) in the presence of NaH and N,N-dimethylformamide.Structure elucidation for all the synthesized compounds was executed by different spectroscopic analysis like IR, 1H-NMR andEI-MS. All the synthesized derivatives were screened for antibacterial activity. Antibacterial potential was sorted out for four gram-negative bacteria including Shigella sonnei, Escherichia coli, Pseudomonas aeruginosa & Salmonella typhi; and two gram-positive bacteria including Bacillus subtilis & Staphylococcus aureus and found results that most of the compounds exhibitsignificant activity relative to the standard drugs Ciprofloxacin and Gentamycin.
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