Chemistry of Iminofuran: XVI. Synthesis,Structure, Biological Activity,and Cyclization of 4-Oxo-2-(2-phenylaminobenzoylhydrazono)butanoic Acids |
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Authors: | Kizimovaa I. A. Igidov N. M. Chaschina S. V. Chernov I. N. Rubtsov A. E. |
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Affiliation: | 1.Perm State Pharmaceutical Academy, ul. Polevaya 2, Perm, 614990, Russia ;2.Scientific Research Institute of Chemistry, Lobachevsky State University of Nizhny Novgorod, pr. Gagarina 23, Nizhny Novgorod, 603022, Russia ;3.Perm State National Research University, ul. Bukireva 15, Perm, 614990, Russia ; |
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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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