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Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity

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Abstract

A number of new octahydro-2H-chromene acetamide derivatives based on the monoterpenoid (−)-isopulegol were synthesized using a one-pot three-component Prins—Ritter reaction. The structure of the target compounds was determined using 1H and 13C NMR spectroscopy, high resolution mass spectrometry, and X-ray diffraction analysis. Most of the products exhibited high analgesic activity in in vivo tests. The highest analgesic activity was found for spirocyclic compound (4S)-2d, the effect of which is apparently mediated through the dopamine system. It was shown that compound (4S)-2d has a low acute toxicity.

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Acknowledgements

The authors are grateful to the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences, for spectral and analytical measurements.

Funding

This study was performed in the framework of State Assignment for the Laboratory of Pharmacological Research, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (NIOC SB RAS), No.1021051402785-4-1.4.1, and the State Assignment for the Laboratory of Physiologically Active Compounds, NIOC SB RAS, No. 1021051703312-0-1.4.1.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    N. S. Li-Zhulanov, Yu. V. Gatilov, K. P. Volcho, M. V. Khvostov, T. G. Tolstikova & N. F. Salakhutdinov

  2. Novosibirsk State University, 1 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    V. A. Kuznetsova

Authors
  1. N. S. Li-Zhulanov
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  2. V. A. Kuznetsova
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  3. Yu. V. Gatilov
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  4. K. P. Volcho
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  5. M. V. Khvostov
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  6. T. G. Tolstikova
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  7. N. F. Salakhutdinov
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Corresponding author

Correspondence to K. P. Volcho.

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Animal Testing and Ethics

The animals were handled in strict compliance with the legislation of the Russian Federation, provisions of the European Convention for the Protection of Vertebrate Animals used for Experimental or other Scientific Purposes (2010), and the requirements and recommendations of the Guidelines for the Care and Use of Laboratory Animals. The animal experiments were approved by the Ethical Committee of the N. N. Vorozhtsov Federal State Budgetary Institution of Science, Siberian Branch, Russian Academy of Sciences (protocol No. P-04-05.2022-14 of 24.05.2022).

Conflict of Interest

The authors declare no competing interests.

Additional information

Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2430–2438, October, 2023.

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Li-Zhulanov, N.S., Kuznetsova, V.A., Gatilov, Y.V. et al. Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity. Russ Chem Bull 72, 2430–2438 (2023). https://doi.org/10.1007/s11172-023-4044-2

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  • DOI: https://doi.org/10.1007/s11172-023-4044-2

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