Lupane and 18αH-oleanane α-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)–C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)–C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 μM) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines.
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This work was carried out with the financial support of the Program of Basic Research of the Presidium of the Russian Academy of Sciences "Basic Sciences for Medicine" (grant 12-R-3-1009) and the Russian Foundation for Basic Research (grant 12-03-31060_mol_a).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 72-83, January, 2014.
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Galaiko, N.V., Nazarov, A.V., Tolmacheva, I.A. et al. Synthesis of Triterpene A-Condensed Azoles. Chem Heterocycl Comp 50, 65–75 (2014). https://doi.org/10.1007/s10593-014-1449-8
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DOI: https://doi.org/10.1007/s10593-014-1449-8