Abstract
A series of 1,5-diarylpyrazoles with a substituted benzenesulfonamide moiety was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Some compounds, for example, (+/-)-2-[4-(5- p-tolyl-3-trifluoromethyl-pyrazole-1-yl)-benzenesulfonylaminooxy]-propionic acid 16 and its disodium salt 21, had a higher in vivo anti-inflammatory activity compared to celecoxib, despite having no in vitro COX-1 or COX-2 inhibitory activity. Their gastrointestinal side effect profile is essentially more favorable than that of celecoxib.
MeSH terms
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Acetic Acid
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Animals
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Carrageenan
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Celecoxib
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Chronic Disease
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Crystallization
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Cyclooxygenase 1 / chemistry
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Cyclooxygenase 1 / metabolism
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Cyclooxygenase 2 / chemistry
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Cyclooxygenase 2 / metabolism
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Cyclooxygenase Inhibitors / chemical synthesis*
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Cyclooxygenase Inhibitors / chemistry
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Cyclooxygenase Inhibitors / pharmacology
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Edema / drug therapy
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Ethanol
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Gastric Mucosa / drug effects
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Gastric Mucosa / pathology
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Hyperalgesia / drug therapy
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Male
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Pyrazoles / chemical synthesis*
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Pyrazoles / chemistry
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Pyrazoles / pharmacology
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Rats
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Rats, Wistar
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Recombinant Proteins / chemistry
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Stereoisomerism
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Stomach Ulcer / chemically induced
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Stomach Ulcer / pathology
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Stomach Ulcer / prevention & control
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Sulfonamides / chemical synthesis*
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Sulfonamides / chemistry
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Sulfonamides / pharmacology
Substances
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Cyclooxygenase Inhibitors
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Pyrazoles
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Recombinant Proteins
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Sulfonamides
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Ethanol
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Carrageenan
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Cyclooxygenase 1
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Cyclooxygenase 2
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Celecoxib
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Acetic Acid