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Mannich Reaction of Solasodine with Acetylenes and Formaldehyde. Cytotoxicity of N-Propargyl-Substituted Alkaloid Derivatives

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The reaction of the steroidal alkaloid solasodine with formaldehyde, terminal arylalkynes, 2-ethynylpyridine, propiolic acid methyl ester, or (trimethylsilyl)acetylene with heating to 100°C in 1,4-dioxane in the presence of CuI synthesized the corresponding N-(prop-2-ynyl)spiro solanes as mixtures of (22R,25R)- and (22S,25R)-diastereomers in 28–81% yields and 1.6–1:1–1.7 ratios of stereoisomers. The cytotoxicities of the new solasodine derivatives against T98G, U-87, MT-4, and MDA-MB-231 human tumor cells were tested in vitro.

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Acknowledgment

The work was supported by a grant from the Russian Science Foundation (Project No. 18-13-00361). We thank staff of the Khimiya Center for Collective Use, SB, RAS, for performing the spectral and analytical studies.

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Authors and Affiliations

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

    A. O. Finke, M. E. Mironov & E. E. Shults

  2. Novosibirsk State University, 1 Pirogova St, Novosibirsk, 630090, Russia

    M. E. Mironov & M. A. Pokrovskii

Authors
  1. A. O. Finke
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  2. M. E. Mironov
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  3. M. A. Pokrovskii
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  4. E. E. Shults
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Corresponding author

Correspondence to E. E. Shults.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2023, pp. 77–82.

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Finke, A.O., Mironov, M.E., Pokrovskii, M.A. et al. Mannich Reaction of Solasodine with Acetylenes and Formaldehyde. Cytotoxicity of N-Propargyl-Substituted Alkaloid Derivatives. Chem Nat Compd 59, 87–93 (2023). https://doi.org/10.1007/s10600-023-03924-w

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  • DOI: https://doi.org/10.1007/s10600-023-03924-w

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