Download PDF
Synlett 2012(1): 120-122  
DOI: 10.1055/s-0031-1289910
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Complex Glycosylated Carboranes for BNCT

Federica Campo, Matteo Mossotti, Luigi Panza*
Università degli Studi del Piemonte Orientale ‘Amedeo Avogadro’, Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, via Bovio 6, 28100 Novara, Italy
Fax: +39(0321)375621; e-Mail: luigi.panza@pharm.unipmn.it;
Further Information

Publication History

Received 22 August
Publication Date:
28 November 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient strategy for the preparation of carboranyl derivatives from a common intermediate containing a sugar moiety functionalized with an azido group is described. Such compounds should allow either the conjugation with peptides or proteins for an improved delivery of the products, or the monitoring of the biodistribution profile.

Key words

BNCT - glycosyl carboranes - labeling - dansyl - nitroxide

    References and Notes

  • 1 Valliant JF. Guenther KJ. King AS. Morel P. Schaffer P. Sogbei OO. Stephenson KA. Coord. Chem. Rev.  2002,  232:  173 
    Search in Google Scholar
  • 2a Tietze LF. Bothe U. Griesbach U. Nakaichi M. Hasegawa T. Nakamura H. Yamamoto Y. Bioorg. Med. Chem.  2001,  9:  1747 
    Search in Google Scholar
  • 2b Ronchi S. Prosperi D. Compostella F. Panza L. Synlett  2004,  1007 
  • 2c Ronchi S. Prosperi D. Thimon C. Morin C. Panza L. Tetrahedron: Asymmetry  2005,  16:  39 
    Search in Google Scholar
  • 3 See, for example: Dean B. Oguchi H. Cai S. Otsuji E. Tashiro K. Hakomori S. Toyokuni T. Carbohydr. Res.  1993,  245:  175 
    Search in Google Scholar
  • 4 Morandi S. Ristori S. Berti D. Panza L. Becciolini A. Martini G. Biochim. Biophys. Acta  2004,  1664:  53 
    Search in Google Scholar
  • 5 Gomez FA. Hawthorne MF. J. Org. Chem.  1992,  57:  1384 
    Search in Google Scholar
  • 6 Sparling BA. Simpson GL. Jamison TF. Tetrahedron  2009,  65:  3270 
    Search in Google Scholar
  • 8 Kane RR. Dreschsel K. Hawthorne MF. J. Am. Chem. Soc.  1993,  115:  8853 
    Search in Google Scholar
  • 9 See, for example: Shao N. Xue J. Guo Z. J. Org. Chem.  2003,  68:  9003 
    Search in Google Scholar
  • 10 Chapuis H. Strazewski P. Tetrahedron  2006,  62:  12108 
    Search in Google Scholar
  • 11 Giovenzana GB. Lay L. Monti D. Palmisano G. Panza L. Tetrahedron  1999,  55:  14123 
    Search in Google Scholar
  • 12 NMR characterization of nitroxide derivatives was performed on the corresponding reduced form to avoid line broadening due to the presence of the free radical (see Supporting Information for details): Lee TD. Keana JFW. J. Org. Chem.  1975,  40:  3145 
    Search in Google Scholar
7

All new compounds gave satisfactory elemental analysis and spectroscopic data (see Supporting Information).