Abstract
Reaction of methyl 4-methoxy-2-dimethylaminomethylene-3-oxobutanoate with arylhydrazines gave methyl 1-aryl-5-(methoxymethyl)-1H-pyrazole-4-carboxylates 1 in high yields. Esters 1 were hydrolyzed to the relative carboxylic acids, which were converted by heating to 1-aryl-5-(methoxymethyl)-1H-pyrazoles 3 in good yields. Reaction of 3 with hydrobromic acid afforded the intermediate 1-aryl-5-(bromomethyl)-1H-pyrazoles, which were converted with potassium cyanide to 1-aryl-1H-pyrazole-5- acetonitriles, whose hydrolysis gave the required 1-aryl-1H-pyrazole-5-acetic acids. Some acids 5 showed a strong antiinflammatory and analgesic activity in rats and mice, respectively, as well as moderate antipyretic and in vito platelet antiaggregating effects.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetates / chemical synthesis*
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Acetates / pharmacology
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Carrageenan
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Collagen / antagonists & inhibitors
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Collagen / pharmacology
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Edema / chemically induced
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Edema / prevention & control
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Fever / chemically induced
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Fever / prevention & control
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Humans
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In Vitro Techniques
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Magnetic Resonance Spectroscopy
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Mice
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Pain Measurement / drug effects
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Platelet Aggregation / drug effects
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Platelet Aggregation Inhibitors / chemical synthesis
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Platelet Aggregation Inhibitors / pharmacology
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Pyrazoles / chemical synthesis*
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Pyrazoles / pharmacology
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Rats
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Spectrophotometry, Infrared
Substances
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Acetates
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Anti-Inflammatory Agents, Non-Steroidal
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Platelet Aggregation Inhibitors
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Pyrazoles
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Carrageenan
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Collagen