Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.2.357

Preparation of Boronated Heterocyclic Compounds Using Intramolecular Cyclization Reaction  

Lee, Chai-Ho (Department of Chemistry and Institute of Basic Natural Science, Wonkwang University)
Jin, Guofan (Department of Chemistry and Institute of Basic Natural Science, Wonkwang University)
Kim, Hyo-Suk (Department of Chemistry, College of Natural Science, Chosun University)
Nakamura, Hiroyuki (Department of Chemistry, Faculty of Science, Gakushuin University)
Chung, Yong-Seog (Department of Chemistry, CBITRC, Chungbuk National University, Cheongju 361-763, Korea)
Lee, Jongdae (Department of Chemistry, College of Natural Science, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.2, 2008 , pp. 357-362 More about this Journal
Abstract
A method for synthesizing o-carborane substituted tetrahydroisoquinolines containing a polar functional group such as sulfamide, sulfonic, or phosphoric acid on the nitrogen atom of the piperidine ring, starting from arylethylamine, N-(2-arylethyl)sulfamide, N-(2-arylethyl)sulfamic acid or 2-arylethylamidophosphate, is described. In vitro studies showed the desired compounds 10, 15, 19, and 25 synthesized accumulate to high levels in B-16 melanoma cells with low cytotoxicity.
Keywords
Brain cancer therapy; Boronated heterocyclic compounds; Cytotoxicity
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Williams, R. E. Chem. Rev. 1992, 92, 177   DOI
2 Yoon, B. H.; Lyu, H. S.; Hahn, J. H.; Ahn, C. M. Bull. Kor. Chem. Soc. 1992, 13, 290
3 Martinez, A.; Gil, C.; Abasolo, M. I.; Castro, A.; Bruno, A. M.; Perez, C.; Prieto, C.; Otero, J. J. Med. Chem. 2000, 43, 3218   DOI   ScienceOn
4 Lee, C.-H.; Kohn, H. J. Org. Chem. 1990, 55, 6098   DOI
5 Lee, C.-H.; Lee, S. M.; Lee, Y. H.; Chung, B. Y. Bull. Kor. Chem. Soc. 1992, 13, 357
6 Shi, D.-F.; Bradshaw, T. D.; Chua, M.-S.; Westwell, A. D.; Stevens, M. F. Bioorg. Med. Chem. Lett. 2001, 11, 1093   DOI   ScienceOn
7 Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341   DOI   ScienceOn
8 Sotomayor, N.; Dominguez, E.; Lete, E. J. Org. Chem. 1996, 61, 4062   DOI   ScienceOn
9 Yinghuai, Z.; Peng, A. T.; Carpenter, K.; Maguire, J. A.; Hosmane, N. S.; Takagaki, M. J. Am. Chem. Soc. 2005, 127, 9875   DOI   ScienceOn
10 Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607   DOI   ScienceOn
11 Locher, G. L. Am. J. Roentgenol. 1936, 36, 632
12 Wilbur, D. S.; Chyan, M.-K.; Hamlin, D. K.; Vessella, R. L.; Wedge, T. J.; Hawthorne, M. F. Bioconjugate Chem. 2007, 18, 1226   DOI   ScienceOn
13 Sibrian-Vazquez, M.; Hao, E.; Jensen, T. J.; Vicente, G. H. Bioconjugate Chem. 2006, 17, 928   DOI   ScienceOn
14 Vyakaranam, K.; Rana, G.; Ratanasuwan, A.; Hosmane, S. N.; Maguire, J. A.; Hosmane, N. S. Organometallics 2002, 21, 3905   DOI   ScienceOn
15 Li, G.-Y.; Li, B.-G.; Yang, T.; Liu, G.-Y.; Zhang, G.-L. Org. Lett. 2006, 8, 3613   DOI   ScienceOn
16 Narayanasamy, S.; Thirumamagal, B. T. S.; Johnsamuel, J.; Byun, Y.; Al-Madhoun, A. S.; Usova, E.; Cosquer, G. Y.; Yan, J.; Bandyopadhyaya, A. K.; Tiwari, R.; Eriksson, S.; Tjarks, W. Bioorg. Med. Chem. 2006, 14, 6886   DOI   ScienceOn
17 Di Meo, C.; Panza, L.; Capitani, D.; Mannian, L.; Banzato, A.; Rondina, M.; Renier, D.; Rosato, A.; Crescenzi, V. Biomacromolecules 2007, 8, 552   DOI   ScienceOn
18 Tietze, L. F.; Bothe, U.; Griesbach, U.; Nakaichi, M.; Hasegawa, T.; Nakamura, H.; Yamamoto, Y. ChemBioChem 2001, 2, 326   DOI   ScienceOn
19 Luo, S.; Zhao, J.; Zhai, H. J. Org. Chem. 2004, 69, 4548   DOI   ScienceOn
20 Magnus, P.; Matthews, K. S. J. Am. Chem. Soc. 2005, 127, 12476   DOI   ScienceOn
21 Magnus, P.; Matthews, K. S.; Lynch, V. Org. Lett. 2003, 5, 2181   DOI   ScienceOn
22 Haushalter, R. C.; Butler, W. M.; Rudolph, R. W. J. Am. Chem. Soc. 1981, 103, 2620   DOI
23 Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968   DOI   ScienceOn
24 Campiani, G.; Butini, S.; Gemma, S.; Nacci, V.; Fattorusso, C.; Catalanotti, B.; Giorgi, G.; Cagnotto, A.; Goegan, M.; Mennini, T.; Minetti, P.; Di Cesare, M. A.; Mastroianni, D.; Scafetta, N.; Galletti, B.; Stasi, M. A.; Castorina, M.; Pacifici, L.; Ghirardi, O.; Tinti, O.; Carminati, P. J. Med. Chem. 2002, 45, 344   DOI   ScienceOn
25 Campiani, G.; Nacci, V.; Bechelli, S.; Ciani, S. M.; Garofalo, A.; Fiorini, I.; Wikstrom, H.; de Boer, P.; Liao, Y.; Tepper, P. G.; Cagnotto, A.; Mennini, T. J. Med. Chem. 1998, 41, 3763   DOI   ScienceOn
26 Yang, J.-E.; In, J.-K.; Lee,, M.-S.; Kwak, J.-H.; Lee, H.; Lee, S. J.; Kang, H.-Y.; Suh, Y.-G.; Jung, J.-K. Bull. Kor. Chem. Soc. 2007, 28, 1401   DOI   ScienceOn