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Synthesis and Analgesic Activity of N-(1-Aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides

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Abstract

The Reformatsky reagent, derived from the methyl 1-bromocyclohexanecarboxylate and zinc, reacts with N′-(arylmethylidene)benzohydrazides, to form N-(1-aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides as a result of intramolecular cyclization of the initial addition products. Structure of the prepared benzamides was proved by single crystal X-ray diffraction analysis. In the case of p-tolualdehyde benzoylhydrazone, the adduct of the Reformatsky reagent to the double carbon–nitrogen bond of the substrate, which not underwent cyclization, was predominantly isolated. The resulting spiroazetidin-2-ones exhibit antinociceptive activity.

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Funding

This work was financially supported by the Perm Scientific and Educational Center “Rational Subsoil Use,” 2023.

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Authors and Affiliations

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

    E. A. Nikiforova, R. R. Makhmudov, D. P. Zverev, M. V. Dmitriev, S. N. Shurov & N. F. Kirillov

  2. Federal Scientific Center for Medical and Preventive Health Risk Management Technologies, 614045, Perm, Russia

    R. R. Makhmudov

Authors
  1. E. A. Nikiforova
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  2. R. R. Makhmudov
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  3. D. P. Zverev
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  4. M. V. Dmitriev
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  5. S. N. Shurov
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  6. N. F. Kirillov
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Corresponding author

Correspondence to E. A. Nikiforova.

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The studies were performed in accordance with all applicable international, national and institutional guidelines for the care and use of animals. The authors declare no conflict of interest.

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Nikiforova, E.A., Makhmudov, R.R., Zverev, D.P. et al. Synthesis and Analgesic Activity of N-(1-Aryl-3-oxo-2-azaspiro[3.5]nonan-2-yl)benzamides. Russ J Gen Chem 93, 1941–1950 (2023). https://doi.org/10.1134/S1070363223080029

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  • DOI: https://doi.org/10.1134/S1070363223080029

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