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.

About the authors

I. A. Kizimovaa

Perm State Pharmaceutical Academy

Email: rubtsov@psu.ru
Russian Federation, ul. Polevaya 2, Perm, 614990

N. M. Igidov

Perm State Pharmaceutical Academy

Email: rubtsov@psu.ru
Russian Federation, ul. Polevaya 2, Perm, 614990

S. V. Chaschina

Perm State Pharmaceutical Academy

Email: rubtsov@psu.ru
Russian Federation, ul. Polevaya 2, Perm, 614990

I. N. Chernov

Scientific Research Institute of Chemistry

Email: rubtsov@psu.ru
Russian Federation, pr. Gagarina 23, Nizhny Novgorod, 603022

A. E. Rubtsov

Perm State National Research University

Author for correspondence.
Email: rubtsov@psu.ru
Russian Federation, ul. Bukireva 15, Perm, 614990

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