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Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

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Abstract

2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (−)-α-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.

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Acknowledgments

Authors are grateful to the Russian Foundation for Basic Research (Grant No 13-03-00206a) for the financial support.

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev av., 9, Novosibirsk, Russian Federation, 630090

    Alla Pavlova, Oksana Mikhalchenko, Artem Rogachev, Irina Il’ina, Dina Korchagina, Yuriy Gatilov, Tat’yana Tolstikova, Konstantin Volcho & Nariman Salakhutdinov

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

    Artem Rogachev, Irina Il’ina, Yuriy Gatilov, Konstantin Volcho & Nariman Salakhutdinov

Authors
  1. Alla Pavlova
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  2. Oksana Mikhalchenko
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  3. Artem Rogachev
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  4. Irina Il’ina
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  5. Dina Korchagina
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  6. Yuriy Gatilov
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  7. Tat’yana Tolstikova
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  8. Konstantin Volcho
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  9. Nariman Salakhutdinov
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Corresponding author

Correspondence to Konstantin Volcho.

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Pavlova, A., Mikhalchenko, O., Rogachev, A. et al. Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols. Med Chem Res 24, 3821–3830 (2015). https://doi.org/10.1007/s00044-015-1426-5

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  • DOI: https://doi.org/10.1007/s00044-015-1426-5

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