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Synthesis and cytotoxicity of allobetulin derivatives

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Abstract

A variety of oxygen-, nitrogen-, sulfur-, and platinum-containing allobetulin derivatives, including those with different positions of double bonds in rings A and B, the penta- and hexacyclic ring A, and the 21-acetyl-20,28-epoxy-18α,19βH-ursanoisomeric cycle E, have been synthesized, and the screening of their antineoplastic activity in vitro (cytotoxicity) has been carried out. A significant cytotoxic activity was exhibited by (3R,5R)-19β,28-epoxy-4,5-seco-18α-olean-3(5)-ozonide toward MeWo melanoma cells and by 2,3-indolo-21β-acetyl-20β,28-epoxy-18α,19βH-ursane toward SR leukosis cells. The 3S,5S-diastereoisomer of the former compound showed no cytotoxicity.

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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, I. E. Smirnova, E. F. Khusnutdinova, N. I. Medvedeva, E. Yu. Yamansarov & I. P. Baikova

  2. Blokhin Russian Oncological Research Center, Kashirskoe sh. 24, Moscow, 115478, Russia

    O. S. Zhukova, L. V. Fetisova & G. N. Apryshko

  3. Institute of Chemistry, Vietnam Academy of Sciences and Technologies, ul. 18 Hoang Quoc Viet, Cau Giay region, Hanoi, Vietnam

    Thanh Tra Nguyen & H. Do Thi Thu

Authors
  1. O. B. Kazakova
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  2. I. E. Smirnova
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  3. E. F. Khusnutdinova
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  4. O. S. Zhukova
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  5. L. V. Fetisova
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  6. G. N. Apryshko
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  7. N. I. Medvedeva
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  8. E. Yu. Yamansarov
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  9. I. P. Baikova
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  10. Thanh Tra Nguyen
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  11. H. Do Thi Thu
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Correspondence to O. B. Kazakova.

Additional information

Original Russian Text © O.B. Kazakova, I.E. Smirnova, E.F. Khusnutdinova, O.S. Zhukova, L.V. Fetisova, G.N. Apryshko, N.I. Medvedeva, E.Yu. Yamansarov, I.P. Baikova, Thanh Tra Nguyen, H. Do Thi Thu, 2014, published in Bioorganicheskaya Khimiya, 2014, Vol. 40, No. 5, pp. 608–617.

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Kazakova, O.B., Smirnova, I.E., Khusnutdinova, E.F. et al. Synthesis and cytotoxicity of allobetulin derivatives. Russ J Bioorg Chem 40, 558–567 (2014). https://doi.org/10.1134/S1068162014050082

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