Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors

A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, furt...

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Published inOriental journal of chemistry Vol. 31; no. 4; pp. 1873 - 1885
Main Authors Alam, Jahangir, Alam, Ozair, Ali, Rahmat, Naim, Mohd, Khan, Suroor
Format Journal Article
LanguageEnglish
Published Bhopal Oriental Scientific Publishing Company 2015
Subjects
Acids
Analgesics
Aromatic compounds
Benzene
Chemical synthesis
Conflicts of interest
Enzymes
Ethanol
Hydrocarbons
Imines
Inflammation
Molecular docking
NMR
Nuclear magnetic resonance
Pain
Pharmacology
Pyrazole
Selectivity
Sulfonamides
Thiadiazoles
New York
United States > US
India
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Summary:A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, further evaluated their in-vivo anti-inflammatory, analgesic and in-vitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo anti-inflammatory with 72.33 and 71.17% inhibition along analgesic activity having 67.89% and 71.37 % respectively. Their selectivity against COX-II enzyme with selectivity index 67.81 and 66.38 was established for 6b and 6m, which is compared with Celecoxib. During the gastric ulceration study, selected compounds couldn’t observed any ulcerogenic effect on gastric mucosa.The in-silico pharmacokinetic profile and molecular docking study exposed very good binding affinity towards the cycloxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.
ISSN:0970-020X
2231-5039
DOI:10.13005/ojc/310404