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
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.