Highly Water-Soluble Carbaborane-Bridged Bis(glycophosphonates)
Sven Stadlbauer
Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany, Fax: +49-341-9739319
Search for more papers by this authorPeter Lönnecke
Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany, Fax: +49-341-9739319
Search for more papers by this authorPeter Welzel
Institut für Organische Chemie, Universität Leipzig, Germany Johannisallee 29, 04103 Leipzig, Germany
Prof. Peter Welzel deceased in July 2008
Search for more papers by this authorEvamarie Hey-Hawkins
Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany, Fax: +49-341-9739319
Search for more papers by this authorSven Stadlbauer
Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany, Fax: +49-341-9739319
Search for more papers by this authorPeter Lönnecke
Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany, Fax: +49-341-9739319
Search for more papers by this authorPeter Welzel
Institut für Organische Chemie, Universität Leipzig, Germany Johannisallee 29, 04103 Leipzig, Germany
Prof. Peter Welzel deceased in July 2008
Search for more papers by this authorEvamarie Hey-Hawkins
Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany, Fax: +49-341-9739319
Search for more papers by this authorGraphical Abstract
The synthesis and properties of highly water-soluble meta- and para-carbaborane-containing bis(galactosyl phosphonates) are presented.
Abstract
A facile synthesis of carbaboranediyl-bis(glycophosphonates) and corresponding phosphonothioates is presented. These compounds show extraordinarily high water solubility and low cytotoxicity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
References
- 1
- 1a M. F. Hawthorne , Angew. Chem. Int. Ed. Engl. 1993 , 32 , 950 –984 .
- 1b 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 –1562 .
- 1c J. F. Valliant , K. J. Guenther , A. S. King , P. Morel , P. Schaffer , O. O. Sogbein , K. A. Stephenson , Coord. Chem. Rev. 2002 , 232 , 173 –230 .
- 2 M. F. Hawthorne , M. W. Lee , J. Neurooncol. 2003 , 62 , 33 –45 .
- 3 R. A. Bechtold , A. Kaczmarczyk , J. Med. Chem. 1975 , 18 , 371 –376 .
- 4 M. W. Lee, K. Shelly, R. R. Kane, M. F. Hawthorne, Advances in Neutron Capture Therapy 2006, Proceedings of ICNCT-12, Chemistry and Pharmacy (Eds.: Y. Nakagawa, T. Kobayashi, H. Fukuda), 2006, p. 234–236.
- 5 W. Tjarks , R. F. Barth , J. H. Rotaru , D. M. Adams , W. Yang , R. G. Kultyshev , J. Forrester , B. A. Barnum , A. H. Soloway , S. G. Shore , Anticancer Res. 2001 , 21 , 841 –846 .
- 6
- 6a M. S. Wadhwa , K. G. Rice , J. Drug Target 1995 , 3 , 111 –127 .
- 6b H. Lis , N. Sharon , Chem. Rev. 1998 , 98 , 637 –674 .
- 6c N. Yamazaki , S. Kojima , N. V. Bovin , S. André , S. Gabius , H.-J. Gabius , Adv. Drug Delivery Rev. 2000 , 43 , 225 –244 .
- 7 B. Dean , H. Oguchi , S. Cai , E. Otsuji , K. Tashiro , S. Hakomori , T. Toyokuni , Carbohydr. Res. 1993 , 245 , 175 –192 .
- 8 S. Stadlbauer , E. Hey-Hawkins , Patent DE 10 2007 038 930.4.
- 9 S. Stadlbauer , P. Welzel , E. Hey-Hawkins , Inorg. Chem. 2009 , 48 , 5005 –5010 .
- 10 G. W. Daub , E. E. van Tamelen , J. Am. Chem. Soc. 1977 , 99 , 3526 –3528 .
- 11
C. E. McKenna
, M. T. Higa
, N. H. Cheung
, M.-C. McKenna
, Tetrahedron Lett.
1977
, 2
, 155
–158
.
10.1016/S0040-4039(01)92575-4 Google Scholar
- 12
- 12a A. Milius , J. Greiner , J. G. Riess , Carbohydr. Res. 1992 , 229 , 323 –336 .
- 12b F. Guillod , J. Greiner , J. G. Riess , Carbohydr. Res. 1994 , 261 , 37 –55 .
- 12c F. Guillod , J. Greiner , J. G. Riess , Chem. Phys. Lipids 1995 , 78 , 149 –162 .
- 13 R. Engel , Chem. Rev. 1977 , 77 , 349 –367 .
- 14 S. J. Kelly , L. G. Butler , Biochem. Biophys. Res. Commun. 1975 , 66 , 316 –321 .
- 15 W. J. Stec , G. Zon , W. Egan , B. Stec , J. Am. Chem. Soc. 1984 , 106 , 6077 –6079 .
- 16
- 16a R. P. Iyer , L. R. Philipps , W. Egan , J. B. Regan , S. L. Beaucage , J. Org. Chem. 1990 , 55 , 4693 –4696 .
- 16b R. P. Iyer , L. R. Philipps , W. Egan , J. B. Regan , S. L. Beaucage , J. Am. Chem. Soc. 1990 , 112 , 1253 –1254 .
- 17 G. B. Giovenzana , L. Lay , D. Monti , G. Palmisano , L. Panza , Tetrahedron 1999 , 55 , 14123 –14136 .
- 18 V. Ya. Komarov , V. I. Zakharov , Yu. V. Belov , B. I. Ionin , Zh. Obshch. Khim. 1980 , 50 , 1262 –1269 .
- 19 S. Berger , S. Braun , 200 and more NMR experiments, Wiley-VCH, 2004 .
- 20 Y. Zhu , J. Zajicek , A. S. Serianni , J. Org. Chem. 2001 , 66 , 6244 –6251 .
- 21 R. P. Alexander , H.-J. Schröder , Inorg. Chem. 1966 , 5 , 493 –495 .
- 22 W. E. Hill , L. M. S. Trivino , Inorg. Chem. 1978 , 17 , 2495 –2498 .
- 23
- 23a S. Stadlbauer , R. Frank , I. Maulana , P. Lönnecke , B. Kirchner , E. Hey-Hawkins , Inorg. Chem. 2009 , 48 , 6072 –6082 .
- 23b V. P. Balema , S. Blaurock , E. Hey-Hawkins , Polyhedron 1999 , 18 , 545 –552 .
- 23c R. Kivekäs , R. Sillanpää , F. Teixidor , C. Vinas , R. Nunez , M. Abad , Acta Crystallogr., Sect. C 1995 , 51 , 1864 –1868 .
- 23d F. Teixidor , C. Vinas , R. Benakki , R. Kivekäs , R. Sillanpää , Inorg. Chem. 1997 , 36 , 1719 –1723 .
- 24 Y. Hayakawa , R. Kawai , A. Hirata , J.-I. Sugimoto , M. Kataoka , A. Sakakura , M. Hirose , R. Noyori , J. Am. Chem. Soc. 2001 , 123 , 8165 –8176 .
- 25 M. Hyodo , Y. Sato , S. Yamashita , A. Hattori , E. Kambe , M. Kataoka , Y. Hayakawa , Tetrahedron 2005 , 61 , 965 –970 .
- 26
- 26a S. Sjöberg , J. Carlsson , H. Ghaneolhosseini , L. Gedda , T. Hartmann , J. Malmquist , C. Naeslund , P. Olsson , W. Tjarks , J. Neuro-Oncol. 1997 , 33 , 41 –52 .
- 26b Z. J. Lesnikowski , J. Shi , R. F. Schinazi , J. Organomet. Chem. 1999 , 581 , 156 –169 .
- 27 Y. Hayakawa , M. Kataoka , R. Noyori , J. Org. Chem. 1996 , 61 , 7996 –7997 .
- 28 CrysAlis Pro, data collection and data reduction software package, Oxford Diffraction Ltd.
- 29 SCALE3 ABSPACK: Empirical absorption correction using spherical harmonics.
- 30 SHELX97 [includes SHELXS97, SHELXL97]: G. M. Sheldrick, 1997. SHELX97, Programs for Crystal Structure Analysis (release 97-2), University of Göttingen, Germany.
- 31 ORTEP3 for Windows: L. J. Farrugia , J. Appl. Crystallogr. 1997 , 30 , 565 .
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