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Synthesis, analgesic and antipyretic activity of 2-(antipyrin-4-yl)hydrazones of 1,2,3-triketones and their derivatives

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Abstract

1,2,3-Triketone 2-(antipyrin-4-yl)hydrazones were synthesized via the azo-coupling reactions of 1,3-diketones with 2-(antipyrin-4-yl)diazonium chloride. The fluoroalkyl-containing hetarylhydrazone enters into cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to yield 3-tetrafluoroethyl derivatives of pyrazole. It was found that 1,2,3-triketone 2-(antipyrin-4-yl)hydrazones and N-(2-hydroxyethyl)-substituted pyrazole exhibit analgesic activity comparable with that of their structural analog analgin (metamizole sodium), but do not possess antipyretic properties. In contrast, N-phenyl-substituted pyrazole did not exhibit analgesic properties but produced a certain antipyretic effect four hours after pyrogenic administration. Fluoroalkyl-containing compounds are less toxic substances than nonfluorinated 2-(antipyrin-4-yl)hydrazone and analgin.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, Russia

    E. V. Shchegol’kov, O. G. Khudina, Ya. V. Burgart & V. I. Saloutin

  2. Institute of Technical Chemistry, Ural Division, Russian Academy of Sciences, Perm, Russia

    L. V. Anikina

Authors
  1. E. V. Shchegol’kov
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  2. O. G. Khudina
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  3. L. V. Anikina
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  4. Ya. V. Burgart
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  5. V. I. Saloutin
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 7, pp. 27 ‣ 29, July, 2006.

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Shchegol’kov, E.V., Khudina, O.G., Anikina, L.V. et al. Synthesis, analgesic and antipyretic activity of 2-(antipyrin-4-yl)hydrazones of 1,2,3-triketones and their derivatives. Pharm Chem J 40, 373–376 (2006). https://doi.org/10.1007/s11094-006-0130-7

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  • DOI: https://doi.org/10.1007/s11094-006-0130-7

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