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Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines

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Various N-containing 18-norlabdanoids were synthesized via reactions of 18-nor-4-amino-15,16-epoxy-8(17),13(16),14-labdatriene with methyl iodide, aromatic aldehydes, acetic and trifluoroacetic acid anhydrides, benzoyl chloride, sulfonyl chlorides, bromoacetic acid chloride, and methyl bromoacetate and condensation with azidobenzoic acids. The cytotoxic activity (MTT assay) against MCF7, HepG2, and HeLa tumor cell lines was shown to increase significantly if the lambertianic acid carboxylic group was replaced by an amine. Subsequent modification of the N-containing substituent by addition of an N′-substituted glycylamide moiety altered the cytotoxicity and selectivity. The synthesized compounds had the greatest effect on the viability of MCF7 cell line. The IC50 value for the most active compound was 8 μM.

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Acknowledgment

The work was financially supported by an RFBR grant and the Novosibirsk Region Administration (Project No. 19-43-540003) and in the framework of a State Task (Projects No. 122040400030-8 and 122040400038-4). We thank staff members of the Khimiya Center for Common Use, Siberian Branch, RAS, for 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

    Yu. V. Kharitonov, V. I. Antipova, M. K. Marenina, Yu. V. Meshkova, T. G. Tolstikova & E. E. Shults

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  1. Yu. V. Kharitonov
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  2. V. I. Antipova
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  3. M. K. Marenina
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  4. Yu. V. Meshkova
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  5. T. G. Tolstikova
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  6. E. E. Shults
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Correspondence to E. E. Shults.

Additional information

For No. 43, see the literature [1].

Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2024, pp. 223–233

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Kharitonov, Y.V., Antipova, V.I., Marenina, M.K. et al. Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines. Chem Nat Compd 60, 252–262 (2024). https://doi.org/10.1007/s10600-024-04299-2

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  • DOI: https://doi.org/10.1007/s10600-024-04299-2

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