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Structure of the cationic forms of pyrimido [4,5-b][1,4]thiazines — A new type of folic acid antagonist

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The protonation of 4-methoxy-, 4-amino-, and 4-dimethylamino-6-aminopyrimido[4,5-b][1,4]thiazines and N-(4-methoxy-5-pyrimidinyl)acetamidine was studied by 1H and 13C NMR spectroscopy. It is shown that the addition of a proton in the first three compounds takes place at the N5 atom of the thiazine ring, whereas in the case of N-(4-methoxy-5-pyrimidinyl) acetamidine primary protonation is observed at the nitrogen atom of the amidine group, and the second proton adds to the N1 atom of the pyrimidine ring.

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Literature cited

  1. N. A. Ryabokon', N. A. Andreeva, M. P. Nemeryuk, A. F. Keremov, V. A. Chernov, and T. S. Safonova, Khim.-farm. Zh., No. 4, 15 (1975).

    Google Scholar 

  2. A. S. Sokolova, N. A. Ryabokon', Yu. A. Ershova, N. A. Andreeva, M. P. Nemeryuk, T. S. Safonova, and V. A. Chernov, Vopr. Onkol., No. 11, 45 (1975).

    Google Scholar 

  3. B. R. Baker, Design of Active Site-Directed Irreversible Enzyme Inhibitors, New York-London (1967).

  4. T. N. Ul'yanova, G. G. Dvoryantseva, Yu. N. Sheinker, A. S. Elina, and I. S. Musatova, Khim. Geterotsikl. Soedin., No. 8, 1115 (1973).

    Google Scholar 

  5. L. M. Alekseeva, G. G. Dvoryantseva, Yu. N. Sheinker, I. A. Mazur, B. V. Kurmaz, and P. M. Kochergin, Khim. Geterotsikl. Soedin., No. 9, 1206 (1974).

    Google Scholar 

  6. R. I. Pugmire, D. M. Grant, M. I. Robins, and R. K. Robins, J. Amer. Chem. Soc., 91, 6381 (1969).

    Google Scholar 

  7. J. A. Lyon, P. D. Ellis, and R. B. Dunlap, Biochemistry, 12, 2425 (1973).

    Google Scholar 

  8. U. Ewers, H. Günter, and L. Jacnicke, Chem. Ber., 107, 3275 (1974).

    Google Scholar 

  9. R. I. Pugmire and D. M. Grant, J. Amer. Chem. Soc., 90, 697 (1968); 93, 1880 (1971).

    Google Scholar 

  10. G. G. Dvoryantseva, T. Ya. Filipenko, I. S. Musatova, A. S. Elina, P. V. Petrovskii, E. V. Arshavskaya, and É. I. Fedin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1060 (1977).

    Google Scholar 

  11. G. G. Dvoryantseva, M. M. Kaganskii, I. S. Musatova, and A. S. Elina, Khim. Geterotsikl. Soedin., No. 11, 1554 (1974).

    Google Scholar 

  12. M. A. Paul and F. A. Long, Chem. Rev., 57, 1 (1957).

    Google Scholar 

  13. E. Högfeldt and J. Bigeleisen, J. Amer. Chem. Soc., 82, 15 (1960).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 49–54, January, 1979.

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Dvoryantseva, G.G., Ul'yanova, T.N., Filipenko, T.Y. et al. Structure of the cationic forms of pyrimido [4,5-b][1,4]thiazines — A new type of folic acid antagonist. Chem Heterocycl Compd 15, 41–46 (1979). https://doi.org/10.1007/BF00471196

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  • DOI: https://doi.org/10.1007/BF00471196

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