2,3-Secolupane aldehydonitriles with an isopropyl fragment were synthesized via Beckman fragmentation of ring A of triterpene α-hydroxyoximes obtained from dihydrobetulonic acid and its methyl ester. Redox transformation of the aldehydonitriles at C-3 led to the formation of the corresponding 3-hydroxy- and 3-carboxy-derivatives. The MTT assay found that only the triterpene oximes possessed moderate cytotoxic activity against HCT 116, RD TE32, MS, and PC-3 tumor cells (IC50 27.8–61.7 μM) among the synthetic products.
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Acknowledgment
The work was financially supported by RSF Grant No. 21-13-00161. We thank the Materials and Compounds Research Common Use Center, PFRC, UrB, RAS, for making it possible to perform the spectral and analytical studies.
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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2022, pp. 588–592.
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Krainova, G.F., Gagarskikh, O.N. & Grishko, V.V. Synthesis of 2,3-Seco-Derivatives of Dihydrobetulonic Acid and its Methyl Ester. Chem Nat Compd 58, 693–698 (2022). https://doi.org/10.1007/s10600-022-03770-2
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DOI: https://doi.org/10.1007/s10600-022-03770-2