Synthesis of boron-containing tyrosine derivatives based on the closo-decaborate and closo-dodecaborate anions
Full Articles
First Online:
Received:
- 88 Downloads
- 2 Citations
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.
Key words
decahydro-closo-decaborate dodecahydro-closo-dodecaborate cyclic oxonium derivatives amino acids tyrosine boron neutron capture therapy of cancerPreview
Unable to display preview. Download preview PDF.
References
- 1.D. Schiff, P. D. Brown, C. Giannini, Neurology, 2007, 69, 1366.CrossRefGoogle Scholar
- 2.A. D. Norden, P. Y. Wen, Neurologist, 2006, 12, 279.CrossRefGoogle Scholar
- 3.M. F. Hawthorne, Angew. Chem., Int. Ed., 1993, 32, 950.CrossRefGoogle 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.CrossRefGoogle Scholar
- 5. (a)I. B. Sivaev, V. I. Bregadze, Ross. Khim. Zh., 2004, 48, № 4, 109 [Mendeleev Chem. J. (Engl. Transl.), 2004, 48, No. 4]Google Scholar
- 5. (b)I. B. Sivaev, V. I. Bregadze, Eur. J. Inorg. Chem., 2009, 1433.Google Scholar
- 6.R. J. DeBerardinis, A. Mancuso, E. Daikhin, I. Nissim, M. Yudkoff, S. Wehrli, C. B. Thompson, Proc. Natl. Acad. Sci. USA, 2007, 104, 19345.CrossRefGoogle Scholar
- 7.J. McConathy, M. M. Goodman, Canc. Metastasis Rev., 2008, 27, 555.CrossRefGoogle Scholar
- 8.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).Google Scholar
- 9. (a)K. J. Langen, K. Hamacher, M. Weckesser, F. Floeth, G. Stoffels, D. Bauer, H. H. Coenen, D. Pauleit, Nucl. Med. Biol., 2006, 33, 287CrossRefGoogle Scholar
- 9. (b)G. Properl, C. Goetz, W. Rachinger, F. J. Gildenhaus, J. C. Tonn, K. Tatsch, Eur. J. Nucl. Med. Mol. Imag., 2004, 31, 1464CrossRefGoogle Scholar
- 9. (c)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.CrossRefGoogle Scholar
- 10.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
- 11. (a)I. B. Sivaev, A. V. Prikaznov, D. Naoufal, Collect. Czech. Chem. Commun., 2010, 75, 1149CrossRefGoogle Scholar
- 11. (b)K. Yu. Zhizhin, A. P. Zhdanov, N. T. Kuznetsov, Zh. Neorg. Khim., 2010, 55 [Russ. J. Inorg. Chem., 2010, 55,2089].Google Scholar
- 12. (a)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
- 12. (b)I. B. Sivaev, V. I. Bregadze, S. Sjöberg, Collect. Czech. Chem. Commun., 2002, 67, 679.CrossRefGoogle Scholar
- 13.I. B. Sivaev, A. A. Semioshkin, B. Brellochs, S. Sjöberg, V. I. Bregadze, Polyhedron, 2000, 19, 627.CrossRefGoogle Scholar
- 14. (a)A. A. Semioshkin, I. B. Sivaev, V. I. Bregadze, Dalton Trans., 2008, 977Google Scholar
- 14. (b)I. B. Sivaev, A. A. Semioshkin, V. I. Bregadze, Appl. Radiat. Isotop., 2009, 67, S91CrossRefGoogle Scholar
- 14. (c)I. B. Sivaev, V. I. Bregadze, in Boron Science: New Technologies and Applications, Ed. N. S. Hosmane, CRC Press, 2011, p. 623.Google Scholar
- 15. (a)R. Bernard, D. Cornu, M. Perrin, J.-P. Schaff, P. Miele, J. Organomet. Chem., 2004, 689, 2581CrossRefGoogle Scholar
- 15. (b)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].Google Scholar
- 16.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.CrossRefGoogle Scholar
- 17. (a)A. Semioshkin, O. Tsareva, O. Zhidkova, V. Bregadze, D. Wőhrle, J. Porphyrins Phthalocyanines, 2006, 10, 1293CrossRefGoogle Scholar
- 17. (b)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
- 18.I. B. Sivaev, S. Sjöberg, V. I. Bregadze, D. Gabel, Tetrahedron Lett., 1999, 40, 3451.CrossRefGoogle Scholar
- 19.A. V. Prikaznov, V. I. Bragin, M. N. Davydova, I. B. Sivaev, V. I. Bregadze, Collect. Czech. Chem. Commun., 2007, 72, 1689.CrossRefGoogle Scholar
- 20.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.CrossRefGoogle Scholar
- 21.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].Google Scholar
- 22.A. Taurog, S. Abraham, I. L. Chaikoff, J. Am. Chem. Soc., 1953, 75, 3473.CrossRefGoogle Scholar
Copyright information
© Springer Science+Business Media New York 2011