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Chemistry of Iminofuran: XVI. Synthesis, Structure, Biological Activity, and Cyclization of 4-Oxo-2-(2-phenylaminobenzoylhydrazono)butanoic Acids

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Abstract

The reaction of (2-phenylaminobenzoyl)hydrazine with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl-4-oxohex-2-enoic acids results in the formation of 4-aryl-2-(2-phenylaminobenzoyl-hydrazono)-4-oxobutanoic and 5,5-dimethyl-2-(2-phenylaminobenzoylhydrazono)-4-oxohexanoic acids. The products in solutions are present as mixtures of a Z,E-hydrazono form and a cyclic pyrazolinic form, and under the action of acetic anhydride they cyclize in 5-aryl- and 5-tert-butyl-3-(2-phenylaminobenzoylhydrazono)-furan-2,3-diones. 4-Aryl-2-(2-phenylaminobenzoylhydrazono)-4-oxobutanoic and 5,5-dimethyl-2-(2-phenyl-aminobenzoylhydrazono)-4-oxohexanoic acids were tested for antinociceptive and anti-inflammatory activity.

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 19-43-590023).

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, ul. Polevaya 2, Perm, 614990, Russia

    I. A. Kizimovaa, N. M. Igidov & S. V. Chaschina

  2. Scientific Research Institute of Chemistry, Lobachevsky State University of Nizhny Novgorod, pr. Gagarina 23, Nizhny Novgorod, 603022, Russia

    I. N. Chernov

  3. Perm State National Research University, ul. Bukireva 15, Perm, 614990, Russia

    A. E. Rubtsov

Authors
  1. I. A. Kizimovaa
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  2. N. M. Igidov
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  3. S. V. Chaschina
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  5. A. E. Rubtsov
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Correspondence to A. E. Rubtsov.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1737–1745.

For communication XV, see [1].

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Kizimovaa, I.A., Igidov, N.M., Chaschina, S.V. et al. Chemistry of Iminofuran: XVI. Synthesis, Structure, Biological Activity, and Cyclization of 4-Oxo-2-(2-phenylaminobenzoylhydrazono)butanoic Acids. Russ J Org Chem 55, 1704–1711 (2019). https://doi.org/10.1134/S1070428019110101

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