Synthesis of N-Functionalized 3,4-o-Carboranylenepiperidines as Potential Boron Neutron Capture Therapy Agents

 

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Abstract

A convenient method for o-carborane-substituted piperidines is described. Product compounds 5a, 5b, 5d, and 5e were found accumulate in B-16 melanoma cells with a significantly high level, although with low cytotoxicity.

References

• 1a Locher GL. Am. J. Roentgenol.  1936,  36:  1 
  CrossrefPubMedGoogle Scholar
• 1b Soloway AH. Tjarks W. Barnum BA. Rong F.-G. Barth RF. Codogni IM. Wilson JG. Chem. Rev.  1998,  98:  1515 
  CrossrefPubMedGoogle Scholar
• 2a Hawthorne MF. Angew. Chem., Int. Ed. Engl.  1993,  32:  950 
  Google Scholar
• 2b Morin C. Tetrahedron  1994,  50:  12521 
  Google Scholar
• 2c Yamamoto Y. Pure. Appl. Chem.  1991,  63:  423 
  Google Scholar
• 2d Barth RF. Soloway AH. Fairchild RG. Cancer Res.  1990,  50:  1061 
  Google Scholar
• 3a Valliant JF. Guenther KJ. King AS. Morel P. Schaffer P. Sogbein OO. Stephenson KA. Coord. Chem. Rev.  2002,  232:  173 
  CrossrefGoogle Scholar
• 3b Morin C. Tetrahedron  1994,  50:  12521 
  CrossrefGoogle Scholar
• 4a Lee C.-H. Lim H.-G. Lee J.-D. Lee Y.-J. Ko J. Nakamura H. Kang SO. Appl. Organometal. Chem.  2003,  17:  539 
  CrossrefGoogle Scholar
• 4b Lee J.-D. Lee C.-H. Nakamura H. Ko J. Kang SO. Tetrahedron Lett.  2002,  43:  5483 
  CrossrefGoogle Scholar
• 5 Lee J.-D. Lee Y.-J. Jeong H.-J. Lee JS. Lee C.-H. Ko J. Kang SO. Organometallics  2003,  22:  445 
  CrossrefGoogle Scholar
• 6 Haushalter RC. Butler WM. Rudolph RW. J. Am. Chem. Soc.  1981,  103:  2620 
  CrossrefGoogle Scholar
• 7a Baker SR. Parsons AF. Wilson M. Tetrahedron Lett.  1998,  39:  331 
  CrossrefGoogle Scholar
• 7b Satoh Y. Marcopulos N. Tetrahedron Lett.  1995,  36:  1759 
  CrossrefGoogle Scholar
• 7c Studer M. Blaser H.-U. J. Mol. Catal. A: Chem.  1996,  112:  437 
  CrossrefGoogle Scholar
• 8 Katritzky AR. Lan X. Yang JZ. Denisko OV. Chem. Rev.  1998,  98:  409 
  CrossrefPubMedGoogle Scholar
• 9a Shi D.-F. Bradshaw TD. Chua M.-S. Westwell AD. Stevens MFG. Bioorg. Med. Chem. Lett.  2001,  11:  1093 
  Google Scholar
• 9b Curran WV. Ross AA. Lee VJ. J. Antibiot.  1988,  XLI(10):  1418 
  Google Scholar
• 10a Kannan T. Vinodhkumar S. Varghese B. Loganathan D. Bioorg. Med. Chem. Lett.  2001,  11:  2433 
  CrossrefGoogle Scholar
• 10b Hammerschmidt F. Hanbauer M. J. Org. Chem.  2000,  65:  6121 
  CrossrefGoogle Scholar
• 10c Brands KMJ. Wiedbrauk K. Williams JM. Dolling U.-H. Reider PJ. Tetrahedron Lett.  1998,  39:  9583 
  CrossrefGoogle Scholar
• 11a Lee C.-H. Kohn H. J. Org. Chem.  1990,  55:  6098 
  CrossrefGoogle Scholar
• 11b Lee C.-H. Korp JD. Kohn H. J. Org. Chem.  1989,  54:  3077 
  CrossrefGoogle Scholar
• 12 Tietze LF. Bothe U. Griesbach U. Nakaichi M. Hasegawa T. Nakamura H. Yamamoto Y. ChemBioChem  2001,  2:  326 
  CrossrefGoogle Scholar