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Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2H-Chromen-4,8-Diols Containing Thiophene Substituents

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Chemistry of Natural Compounds Aims and scope

Hexahydro-2H-chromenes with thiophene fragments were synthesized via reactions of a p-menthane monoterpenoid diol with several thiophenecarboxaldehydes. Most of the synthesized compounds with an additional thiophene fragment displayed analgesic activity in vivo tests at a dose of 10 mg/kg. It was found that the activity in either an acetate-writhing test or a hot-plate test depended on the type and location of substituent in the heteroaromatic ring.

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Acknowledgment

We thank the Russian Foundation for Basic Research for financial support (Grant 15-33-20198) and the Khimiya Center for Collective Use, SB, RAS, for spectral and analytical measurements.

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Authors and Affiliations

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

    A. V. Pavlova, E. V. Nazimova, O. S. Mikhal’chenko, I. V. Il’ina, D. V. Korchagina, O. V. Ardashov, E. A. Morozova, T. G. Tolstikova, K. P. Volcho & N. F. Salakhutdinov

  2. Novosibirsk National Research State University, 2 Pirogova St., Novosibirsk, 630090, Russian Federation

    I. V. Il’ina, O. V. Ardashov, K. P. Volcho & N. F. Salakhutdinov

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  1. A. V. Pavlova
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  2. E. V. Nazimova
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  3. O. S. Mikhal’chenko
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  4. I. V. Il’ina
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  5. D. V. Korchagina
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  6. O. V. Ardashov
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  7. E. A. Morozova
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  8. T. G. Tolstikova
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  9. K. P. Volcho
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  10. N. F. Salakhutdinov
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Corresponding author

Correspondence to I. V. Il’ina.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2016, pp. 698–704.

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Pavlova, A.V., Nazimova, E.V., Mikhal’chenko, O.S. et al. Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2H-Chromen-4,8-Diols Containing Thiophene Substituents. Chem Nat Compd 52, 813–820 (2016). https://doi.org/10.1007/s10600-016-1785-2

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  • DOI: https://doi.org/10.1007/s10600-016-1785-2

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