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Synthesis of New Thiazolyl Coupled Pyrazoles Bearing 2,4-Thiazolidinedionyl Pharmacophore and Their Anti-Inflammatory and Antibacterial Evaluation

[ Vol. 16 , Issue. 1 ]

Author(s):

Lalit Khillare, Manisha Bhosle, Mahendra Bhalerao, Kiran Kharat and Ramrao Mane   Pages 46 - 57 ( 12 )

Abstract:


Background: 2, 4-Thiazolidinedione (TZD), pyrazole and thiazole heterocyclic rings exhibit a wide range of pharmacological activities. Medicinal chemists use these heterocyclic moieties as scaffolds in drug designing and discovery. The existing medicaments, celecoxib and meloxicam, used for treating inflammation and pain are having, pyrazole and thiazole, respectively as key scaffolds. Pyrazoles coupled with 2, 4-thiazolidinediones may display enhanced anti-inflammatory activity. With this hope the bench work was carried out.

Methods: Heterocyclic aldehydes, 3-(4-methyl-2-substituted thiazol-5-yl)-1-phenyl-1Hpyrazole- 4- carbaldehydes (4a-b) have been allowed to undergo Knoevenagel condensation with N-substituted 2,4-thiazolidinediones (5a-e) in PEG-400 in the presence of L-proline at 110°C and obtained the condensed products (6a-j). COX-2 evaluation of the titled product has been carried out using in vitro COX-2 ELISA Kit. Antibacterial activity of these compounds (6a-j) has also been determined.

Results: On the basis of 1H NMR, 13C NMR and Mass spectral data of the condensed products the structures have been assigned to (Z)-5-((3-(4-methyl-2-substituted thiazol-5-yl)-1- phenyl-1H-pyrazol-4-yl)methylene) 3-substituted thiazolidine-2,4-diones (6a-j). Among the evaluated compounds (6a-j), 6f, 6g, 6h, 6i and 6j have shown notable COX-2 inhibitory activity.

Conclusion: Compounds, 6a, 6b, 6c, 6d, 6e and 6f have inhibited the growth of the Bacillus cereus NCIM 2106, Bacillus subtilis NCIM 2063, Pseudomonas aeruginosa NCIM 2074, Salmonella typhimurium NCIM 2501 and Staphylococcus aureus NCIM 2079. However, compound 6f has emerged as a suitable candidate with dual properties i.e. COX-2 inhibitory and antibacterial in the present study.

Keywords:

2, 4-thiazolidinedione, antibacterial activity, COX-2 Inhibitors, pyrazole, thiazole.

Affiliation:

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad (MS) 431 004, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad (MS) 431 004, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad (MS) 431 004, Department of Biotechnology, Deogiri College, Aurangabad (MS) 431 004, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad (MS) 431 004

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