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  • Title: [Azoles. 17. Beta-(4-pyrazol)acrylic and propionic acids and their anti-inflammatory activity].
    Author: Bernard M, Hulley E, Molenda H, Stochla K, Wrzeciono U.
    Journal: Pharmazie; 1986 Aug; 41(8):560-2. PubMed ID: 3786374.
    Abstract:
    beta-(4-Pyrazole)acrylic acids 22-28 were prepared by the Knoevenagel reaction of malonic acid and 4-formylpyrazoles 8-14. 4-Pyrazolemethylenemalonic acids 15-21 were isolated as intermediates. The latter compounds were also synthesized by treating the 4-formylpyrazoles 8-14 with diethyl malonate followed by hydrolysis of the obtained diethyl esters 15a-21a. The effect of piperidine and pyridine on the Knoevenagel condensation was investigated. The beta-(4-pyrazole)acrylic acids 22-27, on catalytic reduction, gave the corresponding beta-(4-pyrazole)propionic acids 29-34. Compounds 23, 24, 27, 29-31 and 34 appeared to be less active than phenylbutazone in carrageenin-induced oedema test, but they were less toxic than the reference drug.
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