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Synthesis and cytotoxicity of allobetulin derivatives

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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Correspondence to O. B. Kazakova.

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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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  • DOI: https://doi.org/10.1134/S1068162014050082

Keywords

  • triterpenoids
  • allobetulin
  • synthesis
  • cytotoxicity