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

Chai-Ho Lee; Il Doo Yang; Jong-Dae Lee; Hiroyuki Nakamura; Jaejung Ko; Sang Ook Kang

doi:10.1055/s-2004-829544

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2004(10): 1799-1801
DOI: 10.1055/s-2004-829544

LETTER

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

Chai-Ho Lee*^a, Il Doo Yang^a, Jong-Dae Lee^b, Hiroyuki Nakamura^c, Jaejung Ko*^b, Sang Ook Kang*^b
^a Department of Chemistry and Institute of Basic Natural Science, Wonkwang University, Iksan, Jeonbuk 570-749, South Korea
^b Department of Chemistry, Korea University, 208 Seochang, Chungnam 339-700, South Korea
^c Department of Chemistry, Faculty of Science, Gakushuin University, Toshima, Tokyo 171-8588, Japan
Fax: +82(41)8675396; e-Mail: sangok@korea.ac.kr;

Further Information

Publication History

Received 14 May 2004
Publication Date:
15 July 2004 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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.

Key words

BNCT - o-carborane - boron cage - benzylamine - metal catalyzed hydrogenation

References

1a Locher GL. Am. J. Roentgenol. 1936, 36: 1

Crossref PubMed Search in Google Scholar
1b Soloway AH. Tjarks W. Barnum BA. Rong F.-G. Barth RF. Codogni IM. Wilson JG. Chem. Rev. 1998, 98: 1515

Crossref PubMed Search in Google Scholar
2a Hawthorne MF. Angew. Chem., Int. Ed. Engl. 1993, 32: 950

Search in Google Scholar
2b Morin C. Tetrahedron 1994, 50: 12521

Search in Google Scholar
2c Yamamoto Y. Pure. Appl. Chem. 1991, 63: 423

Search in Google Scholar
2d Barth RF. Soloway AH. Fairchild RG. Cancer Res. 1990, 50: 1061

Search in Google Scholar
3a Valliant JF. Guenther KJ. King AS. Morel P. Schaffer P. Sogbein OO. Stephenson KA. Coord. Chem. Rev. 2002, 232: 173

Crossref Search in Google Scholar
3b Morin C. Tetrahedron 1994, 50: 12521

Crossref Search in Google 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

Crossref Search in Google Scholar
4b Lee J.-D. Lee C.-H. Nakamura H. Ko J. Kang SO. Tetrahedron Lett. 2002, 43: 5483

Crossref Search in Google Scholar
5 Lee J.-D. Lee Y.-J. Jeong H.-J. Lee JS. Lee C.-H. Ko J. Kang SO. Organometallics 2003, 22: 445

Crossref Search in Google Scholar
6 Haushalter RC. Butler WM. Rudolph RW. J. Am. Chem. Soc. 1981, 103: 2620

Crossref Search in Google Scholar
7a Baker SR. Parsons AF. Wilson M. Tetrahedron Lett. 1998, 39: 331

Crossref Search in Google Scholar
7b Satoh Y. Marcopulos N. Tetrahedron Lett. 1995, 36: 1759

Crossref Search in Google Scholar
7c Studer M. Blaser H.-U. J. Mol. Catal. A: Chem. 1996, 112: 437

Crossref Search in Google Scholar
8 Katritzky AR. Lan X. Yang JZ. Denisko OV. Chem. Rev. 1998, 98: 409

Crossref PubMed Search in Google Scholar
9a Shi D.-F. Bradshaw TD. Chua M.-S. Westwell AD. Stevens MFG. Bioorg. Med. Chem. Lett. 2001, 11: 1093

Search in Google Scholar
9b Curran WV. Ross AA. Lee VJ. J. Antibiot. 1988, XLI(10): 1418

Search in Google Scholar
10a Kannan T. Vinodhkumar S. Varghese B. Loganathan D. Bioorg. Med. Chem. Lett. 2001, 11: 2433

Crossref Search in Google Scholar
10b Hammerschmidt F. Hanbauer M. J. Org. Chem. 2000, 65: 6121

Crossref Search in Google Scholar
10c Brands KMJ. Wiedbrauk K. Williams JM. Dolling U.-H. Reider PJ. Tetrahedron Lett. 1998, 39: 9583

Crossref Search in Google Scholar
11a Lee C.-H. Kohn H. J. Org. Chem. 1990, 55: 6098

Crossref Search in Google Scholar
11b Lee C.-H. Korp JD. Kohn H. J. Org. Chem. 1989, 54: 3077

Crossref Search in Google Scholar
12 Tietze LF. Bothe U. Griesbach U. Nakaichi M. Hasegawa T. Nakamura H. Yamamoto Y. ChemBioChem 2001, 2: 326

Crossref Search in Google Scholar