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Synthesis and Analgesic Activity of N,6-Diaryl-4-hydroxy-4-methyl-2-oxocyclohexane-1-carboxamides and Their Dehydration Products

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Abstract

A series of new N,6-diaryl-4-hydroxy-4-methyl-2-oxocyclohexane-1-carboxamides was obtained through the reaction of N-arylamides of acetoacetic acid with benzalacetone and 4-chlorobenzalacetone under basic conditions (KOH) in methanol at room temperature. Increasing of the amount of potassium hydroxide used in the reaction led to the formation of dehydration products, namely N,6-diaryl-4-methyl-2-oxocyclohex-3-ene-1-carboxamides. The latter were also formed by using unsubstituted acetoacetamide and N-methylacetoacetamide. The synthesized compounds were tested for analgesic activity.

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Funding

This work was supported by the St. Petersburg State University (Application for the development of the material and technical base of St. Petersburg State University no. 33402376) using the equipment of the Resource Centers “Chemical Analysis and Materials Research Center,” “SPbU Computing Center,” “Magnetic Resonance Research Center,” and the Chemistry Educational Center of the Research Park of St. Petersburg State University.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, 614990, Perm, Russia

    N. V. Nosova, A. A. Sokolov, O. N. Gein & V. L. Gein

  2. National Research University ITMO, 197101, St. Petersburg, Russia

    A. N. Yankin

  3. St. Petersburg State University, 199034, St. Petersburg, Russia

    S. E. Danilov

  4. Perm State National Research University, 614990, Perm, Russia

    M. V. Dmitriev

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  1. N. V. Nosova
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  2. A. A. Sokolov
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  3. O. N. Gein
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  4. V. L. Gein
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Correspondence to V. L. Gein.

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Nosova, N.V., Sokolov, A.A., Gein, O.N. et al. Synthesis and Analgesic Activity of N,6-Diaryl-4-hydroxy-4-methyl-2-oxocyclohexane-1-carboxamides and Their Dehydration Products. Russ J Gen Chem 90, 1581–1590 (2020). https://doi.org/10.1134/S1070363220090017

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