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A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles: Synthesis and Anti-Inflammatory Activity

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Abstract—

In the reaction of coumarin peuruthenicin with α,ω-dibromoalkanes, the corresponding 7-(ω-bromoalkyloxy)coumarins have been synthesized. The interaction of the resulting compounds with sodium azide has yielded 7-(ω-azidoalkyl)-substituted peuruthenicin derivatives, which exhibited high activity in the Cu(I)-catalyzed Huisgen cycloaddition reaction with the propargyl ester of betulonic acid. As a result of the reaction, 28-O-(chromenoalkyl-triazolylmethyl)lupenones have been synthesized. The reaction of betulonic acid propargyl ester with 2-azidooreoselones in the presence of aqueous copper sulfate and sodium ascorbate has led to the corresponding (furochromen-triazolyl)-20(29)-lupen-3-ones. The newly synthesized hybrid compound triterpenoid furocoumarin containing a triazole linker exhibits anti-inflammatory activity in a model of histamine inflammation.

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ACKNOWLEDGMENTS

The authors would like to thank the Chemical Service Center for Collective Use (Siberian Branch, Russian Academy of Sciences) for conducting the spectral and analytical studies.

Funding

The study was supported by the Russian Science Foundation (projects nos. 17-73-10099, 18-13-00361).

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Authors and Affiliations

  1. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    A. V. Lipeeva, M. P. Dolgikh & E. E. Shults

  2. Novosibirsk State University, 630090, Novosibirsk, Russia

    T. G. Tolstikova & E. E. Shults

Authors
  1. A. V. Lipeeva
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  2. M. P. Dolgikh
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  3. T. G. Tolstikova
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  4. E. E. Shults
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Corresponding author

Correspondence to E. E. Shults.

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COMPLIANCE WITH ETHICAL STANDARDS

All experiments were performed in accordance with the European Convention for the Protection of Vertebrate Animals Used for Experimental and Other Scientific Purposes, 1986.

Conflict of Interests

The authors declare that there is no conflict of interest.

Additional information

Translated by S. Sidorova

Abbreviations: AZT, 3-azido-26,3'-deoxythymidine.

For communication 17, see [1].

Corresponding author: phone: +7 (383) 330-85-33; fax: +7 (383) 330-97-52; e-mail: schultz@nioch.nsc.ru.

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Lipeeva, A.V., Dolgikh, M.P., Tolstikova, T.G. et al. A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles: Synthesis and Anti-Inflammatory Activity. Russ J Bioorg Chem 46, 125–132 (2020). https://doi.org/10.1134/S1068162020010161

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  • DOI: https://doi.org/10.1134/S1068162020010161

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