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Influence of spatial effects on the oxidation of cardenolides and bufadienolides containing aldehyde groups

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Abstract

The reactivity of a number of aglycones and glycosides with a cardiac action containing a carbonyl group at C10 is considered. The study was based on the use of the oxidation reaction in the presence of diethylamine, the excess of which after the binding of the hydrochloric acid liberated in the reaction was backtitrated with percholoric acid in methanol. The rate constants of 15 compounds have been determined and it has been established that their reactivity depends on their structure: the nature of the linkage of the A/B rings of the steroid skeleton, the position of a double bond in it, the introduction of a sugar or acetyl group in position 3 of the aglycon, and the nature of the sugar.

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Literature cited

  1. N. A. Kazarinov and N. P. Dzyuba, in: Proceedings of the IIIrd All-Union Conference on the Analytical Chemistry of Nonaqueous Solutions and Their Physicochemical Properties. Part 1. The Analytical Chemistry of Nonaqueous Solutions [in Russian], Gor'kii (1974), p. 104.

  2. N. A. Kazarinov, N. F. Komissarenko, L. B. Nel'zeva, and N. S. Solodun, An Investigation of Drugs and Their Provision for the Population. Interdepartmental Collection of Scientific Papers [in Russian], Sverdlovsk (1983), p. 7.

  3. I. P. Kovalev, E. V. Titov, V. T. Chernobai, and N. F. Komissarenko, Ukr. Khim Zh., 513 (1965).

  4. V. T. Chernobai, Khim. Prir. Soedin., 229 (1965).

  5. I. P. Kovalev and V. T. Chernobai, Khim. Prir. Soedin., 179 (1966).

  6. L. Nover, G. Baumgarten, and M. Luckner, J. Chromatogr., 39, 450 (1969).

    Article  CAS  Google Scholar 

  7. N. F. Komissarenko, Khim. Prir. Soedin., 141 (1969).

  8. I. L. Shamovskii, G. M. Barenboim, and A. A. Ovhinnikov, Bioorg. Khim.,11, 113 (1985).

    CAS  PubMed  Google Scholar 

  9. J. F. Stoddart, Stereochemistry of Carbohydrates, Interscience, New York (1971) [Russian translation, Moscow (1975), p. 304].

    Google Scholar 

  10. R. Tschesche, S. Goenechea, and G. Snatzke, Ann. Chem.,674, 176 (1964).

    Article  CAS  Google Scholar 

  11. V. P. Georgievs'kii, M. O. Kazarinov, and E. I. Puchkova, Farmats. Zh.,3, 54 (1971).

    Google Scholar 

  12. K. B. Yatsimirskii, Kinetic Methods of Analysis [in Russian], Moscow (1967), p. 17.

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All-Union Scientific-Research Institute of Drug Chemistry and Technology, Khar'kov. Translated from Khimiya Prirodnykh Soedinenii, Nö. 5, pp. 602–607, September–October, 1986.

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Kazarinov, M.A., Komissarenko, N.F., Nel'zeva, L.B. et al. Influence of spatial effects on the oxidation of cardenolides and bufadienolides containing aldehyde groups. Chem Nat Compd 22, 566–571 (1986). https://doi.org/10.1007/BF00599262

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