Skip to main content
Log in

Synthesis of boron-containing tyrosine derivatives based on the closo-decaborate and closo-dodecaborate anions

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A series of new boron-containing tyrosine derivatives [B n H n−1O(CH2)4O-4-C6H4CH2CH-(NH3)COOH] and [B n H n−1O(CH2CH2)2O-4-C6H4CH2CH(NH3)COOH] (n = 10, 12) were prepared by ring opening of the cyclic oxonium derivatives of the decahydro-closo-decaborate and dodecahydro-closo-dodecaborate anions, respectively, with ethyl N-trifluoroacetyl-L-tyrosinate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D. Schiff, P. D. Brown, C. Giannini, Neurology, 2007, 69, 1366.

    Article  Google Scholar 

  2. A. D. Norden, P. Y. Wen, Neurologist, 2006, 12, 279.

    Article  Google Scholar 

  3. M. F. Hawthorne, Angew. Chem., Int. Ed., 1993, 32, 950.

    Article  Google Scholar 

  4. A. H. Soloway, W. Tjarks, B. A. Barnum, F.-G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson, Chem. Rev., 1998, 98, 1515.

    Article  CAS  Google Scholar 

  5. I. B. Sivaev, V. I. Bregadze, Ross. Khim. Zh., 2004, 48, № 4, 109 [Mendeleev Chem. J. (Engl. Transl.), 2004, 48, No. 4]

    CAS  Google Scholar 

  6. I. B. Sivaev, V. I. Bregadze, Eur. J. Inorg. Chem., 2009, 1433.

  7. R. J. DeBerardinis, A. Mancuso, E. Daikhin, I. Nissim, M. Yudkoff, S. Wehrli, C. B. Thompson, Proc. Natl. Acad. Sci. USA, 2007, 104, 19345.

    Article  CAS  Google Scholar 

  8. J. McConathy, M. M. Goodman, Canc. Metastasis Rev., 2008, 27, 555.

    Article  Google Scholar 

  9. T. Yu. Skvortsova, Z. L. Brodskaya, M. S. Rudas, G. V. Kataeva, A. F. Gurchin, S. V. Medvedev, Med. vizualizatsiya [Med. visualization], 2001, No. 1, 67 (in Russian).

  10. K. J. Langen, K. Hamacher, M. Weckesser, F. Floeth, G. Stoffels, D. Bauer, H. H. Coenen, D. Pauleit, Nucl. Med. Biol., 2006, 33, 287

    Article  CAS  Google Scholar 

  11. G. Properl, C. Goetz, W. Rachinger, F. J. Gildenhaus, J. C. Tonn, K. Tatsch, Eur. J. Nucl. Med. Mol. Imag., 2004, 31, 1464

    Article  Google Scholar 

  12. M. Weckesser, K. J. Langen, C. H. Rickert, S. Kloska, R. Straeter, K. Hamacher, H. Kurlemann, G. Wassmann, H. H. Coenen, O. Schober, Eur. J. Nucl. Med. Mol. Imag., 2005, 32, 422.

    Article  CAS  Google Scholar 

  13. I. A. Lobanova, M. Ya. Berzina, I. B. Sivaev, P. V. Petrovskii, V. I. Bregadze, Izv. Akad. Nauk, Ser. Khim., 2010, 2246 [Russ. Chem. Bull., Int. Ed., 2010, 59, 2302].

    Google Scholar 

  14. I. B. Sivaev, A. V. Prikaznov, D. Naoufal, Collect. Czech. Chem. Commun., 2010, 75, 1149

    Article  CAS  Google Scholar 

  15. K. Yu. Zhizhin, A. P. Zhdanov, N. T. Kuznetsov, Zh. Neorg. Khim., 2010, 55 [Russ. J. Inorg. Chem., 2010, 55,2089].

  16. I. B. Sivaev, V. I. Bregadze, N. T. Kuznetsov, Izv. Akad. Nauk, Ser. Khim., 2002, 1256 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1362]

    Google Scholar 

  17. I. B. Sivaev, V. I. Bregadze, S. Sjöberg, Collect. Czech. Chem. Commun., 2002, 67, 679.

    Article  CAS  Google Scholar 

  18. I. B. Sivaev, A. A. Semioshkin, B. Brellochs, S. Sjöberg, V. I. Bregadze, Polyhedron, 2000, 19, 627.

    Article  CAS  Google Scholar 

  19. A. A. Semioshkin, I. B. Sivaev, V. I. Bregadze, Dalton Trans., 2008, 977

  20. I. B. Sivaev, A. A. Semioshkin, V. I. Bregadze, Appl. Radiat. Isotop., 2009, 67, S91

    Article  CAS  Google Scholar 

  21. I. B. Sivaev, V. I. Bregadze, in Boron Science: New Technologies and Applications, Ed. N. S. Hosmane, CRC Press, 2011, p. 623.

  22. R. Bernard, D. Cornu, M. Perrin, J.-P. Schaff, P. Miele, J. Organomet. Chem., 2004, 689, 2581

    Article  CAS  Google Scholar 

  23. K. Yu. Zhizhin, V. N. Mustyatsa, E. A. Malinina, E. Yu. Matveev, L. V. Goeva, I. N. Polaykova, N. T. Kuznetsov, Zh. Neorg. Khim., 2005, 50, 243 [Russ. J. Inorg. Chem. (Engl. Transl.), 2005, 50, 203].

    CAS  Google Scholar 

  24. A. V. Prikaznov, A. V. Shmal’ko, I. B. Sivaev, P. V. Petrovskii, V. I. Bragin, A. V. Kisin, V. I. Bregadze, Polyhedron, 2011, 30, 1494.

    Article  CAS  Google Scholar 

  25. A. Semioshkin, O. Tsareva, O. Zhidkova, V. Bregadze, D. Wőhrle, J. Porphyrins Phthalocyanines, 2006, 10, 1293

    Article  CAS  Google Scholar 

  26. A. A. Semioshkin, Yu. N. Las’kova, O. B. Zhidkova, V. I. Bregadze, Izv. Akad. Nauk, Ser. Khim., 2008, 1961 [Russ. Chem. Bull., Int. Ed., 2008, 57, 1996].

    Google Scholar 

  27. I. B. Sivaev, S. Sjöberg, V. I. Bregadze, D. Gabel, Tetrahedron Lett., 1999, 40, 3451.

    Article  CAS  Google Scholar 

  28. A. V. Prikaznov, V. I. Bragin, M. N. Davydova, I. B. Sivaev, V. I. Bregadze, Collect. Czech. Chem. Commun., 2007, 72, 1689.

    Article  CAS  Google Scholar 

  29. I. B. Sivaev, N. Yu. Kulikova, E. A. Nizhnik, M. V. Vichuzhanin, Z. A. Starikova, A. A. Semioshkin, V. I. Bregadze, J. Organomet. Chem., 2008, 693, 519.

    Article  CAS  Google Scholar 

  30. K. Yu. Zhizhin, V. N. Mustyatsa, E. A. Malinina, N. A. Votinova, E. Yu. Matveev, L. V. Goeva, I. N. Polyakova, N. T. Kuznetsov, Zh. Neorg. Khim., 2004, 49, 221 [Russ. J. Inorg. Chem. (Engl. Transl.), 2004, 49, 180].

    CAS  Google Scholar 

  31. A. Taurog, S. Abraham, I. L. Chaikoff, J. Am. Chem. Soc., 1953, 75, 3473.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. B. Sivaev.

Additional information

Dedicated to the Academician of the Russian Academy of Sciences R. Z. Sagdeev on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2501–2505, December, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Prikaznov, A.V., Las’kova, Y.N., Semioshkin, A.A. et al. Synthesis of boron-containing tyrosine derivatives based on the closo-decaborate and closo-dodecaborate anions. Russ Chem Bull 60, 2550–2554 (2011). https://doi.org/10.1007/s11172-011-0392-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0392-4

Key words

Navigation