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Synthetic transformation of higher terpenoids 31. Synthesis of 1,2,3-triazolyl-containing furan labdanoids and studies of their cytotoxic activity

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Abstract

16-(1-R-1,2,3-Triazol-4-ylethyl)-, 16-(1-R-1,2,3-triazol-4-ylmethoxymethyl)-, and 16-{2-(1-R-1,2,3-triazol-4-yl)-1-[(1-R-1,2,3-triazol-4-ylmethoxy)ethyl]}-substituted derivatives of methyl lambertianate were synthesized by 1,3-cycloaddition of labdanoid alkynes with azides. The compounds obtained possess considerable cytotoxicity toward the human tumor cell lines CEM-13, MT-4, and U-937. The most active compound, methyl 16-(2-{2-[(1-benzyl-1H-1,2,3-triazol-4-yl)acetyl]furan-3-yl}ethyl)lambertianate, was found to inhibit the viability of the tumor cells by 50% (CCID50) in the concentration of 7–12 μmol L−1.

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Authors and Affiliations

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

    Yu. V. Kharitonov, E. E. Shul’ts, M. M. Shakirov & G. A. Tolstikov

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

    M. A. Pokrovskii & A. G. Pokrovskii

Authors
  1. Yu. V. Kharitonov
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  2. E. E. Shul’ts
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  3. M. M. Shakirov
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  4. M. A. Pokrovskii
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  5. A. G. Pokrovskii
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  6. G. A. Tolstikov
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Corresponding author

Correspondence to E. E. Shul’ts.

Additional information

For Part 30, see Ref. 1

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2046–2055, September, 2013.

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Kharitonov, Y.V., Shul’ts, E.E., Shakirov, M.M. et al. Synthetic transformation of higher terpenoids 31. Synthesis of 1,2,3-triazolyl-containing furan labdanoids and studies of their cytotoxic activity. Russ Chem Bull 62, 2046–2055 (2013). https://doi.org/10.1007/s11172-013-0297-5

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  • DOI: https://doi.org/10.1007/s11172-013-0297-5

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