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Synthesis and cytotoxicity of triterpene seven-membered cyclic amines

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Abstract

3-Deoxy-3a-homo-3a-aza derivatives of betulin and erythrodiol have been synthesized from betulonic and oleanonic acids. 3-Deoxy-3a-homo-3a-aza-28-hydroxy-12(13)-oleanene showed the highest antineoplastic activity of the broad spectrum in vitro; the results of an extensive examination of the derivative in vitro enable one to recommend it for in vivo tests. The modification of the compound in the position C28 by the introduction of a methoxycinnamoyl fragment led to the loss of the antineoplastic activity. As a whole, 3-deoxy-3a-homo-3a-aza derivatives of betulin [3-(aminopropyl)-, 28-(2-carboxyethyl)carboxy-, and 28-cinamoyloxy-] exhibited a moderate antineoplastic activity toward large intestine cancer, breast cancer, and leukemia cells.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia

    O. B. Kazakova, G. V. Giniyatullina, N. I. Medvedeva, T. V. Lopatina, I. P. Baikova & G. A. Tolstikov

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  1. O. B. Kazakova
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  2. G. V. Giniyatullina
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  3. N. I. Medvedeva
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  4. T. V. Lopatina
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  5. I. P. Baikova
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  6. G. A. Tolstikov
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  7. G. N. Apryshko
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Corresponding author

Correspondence to O. B. Kazakova.

Additional information

Original Russian Text © O.B. Kazakova, G.V. Giniyatullina, N.I. Medvedeva, T.V. Lopatina, I.P. Baikova, G.A. Tolstikov, G.N. Apryshko, 2014, published in Bioorganicheskaya Khimiya, 2014, Vol. 40, No. 2, pp. 217–225.

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Kazakova, O.B., Giniyatullina, G.V., Medvedeva, N.I. et al. Synthesis and cytotoxicity of triterpene seven-membered cyclic amines. Russ J Bioorg Chem 40, 198–205 (2014). https://doi.org/10.1134/S106816201402006X

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  • DOI: https://doi.org/10.1134/S106816201402006X

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