Abstract
A series of novel N-(3-substituted aryl/alkyl-4-oxo-1,3-thiazolidin-2-ylidene)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamides 2a–e were synthesized by the addition of ethyl α-bromoacetate and anhydrous sodium acetate in dry ethanol to N-(substituted aryl/alkylcarbamothioyl)-4-[5-(4-methylphenyl)-3-(trifluoro-methyl)-1H-pyrazol-1-yl]benzene sulfonamides 1a–e, which were synthesized by the reaction of alkyl/aryl isothiocyanates with celecoxib. The structures of the isolated products were determined by spectral methods and their anti-inflammatory, analgesic, antioxidant, anticancer and anti-HCV NS5B RNA-dependent RNA polymerase (RdRp) activities evaluated. The compounds were also tested for gastric toxicity and selected compound 1a was screened for its anticancer activity against 60 human tumor cell lines. These investigations revealed that compound 1a exhibited anti-inflammatory and analgesic activities and further did not cause tissue damage in liver, kidney, colon and brain compared to untreated controls or celecoxib. Compounds 1c and 1d displayed modest inhibition of HCV NS5B RdRp activity. In conclusion, N-(ethylcarbamothioyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (1a) may have the potential to be developed into a therapeutic agent.
Highlights
Arachidonic acid is an unsaturated fatty acid liberated from phospholipids of cell membranes.Phospholipid hydrolyses cause arachidonic acid release
We report the synthesis of celecoxib derivatives bearing sulfonylthiourea and
N-(3-Substituted-4-oxo1,3-thiazolidine-2-ylidene)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide derivatives 2a–e were synthesized by the reaction of ethyl -bromoacetate and anhydrous sodium acetate in dry ethanol with the sulfonylthioureas 1a–e
Summary
Arachidonic acid is an unsaturated fatty acid liberated from phospholipids of cell membranes. The eicosanoids are formed by two different routes; namely via the cyclooxygenase (COX) and lipoxygenase (LOX) pathways. Leukotrienes, derived from the lipoxygenase pathway, are responsible for allergy, inflammation and other pathological situations. Cyclic endoperoxides, derived from cyclooxygenase pathway, are converted to derivatives of prostacyclin, prostaglandin E, prostaglandin F2 , tromboxane A2 under the action of several enzymes. Prostacyclins and prostaglandins (PG) are major mediators of hyperalgesia which means sensitization of central neurons and an increased response to a painful stimulus. Hyperalgesia is induced by non-steroidal anti-inflammatory drugs (NSAIDs) with the inhibition of cyclooxygenases
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