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A Concise Synthesis of 8-Oxoberberine and Oxychelerythrine, Natural Isoquinoline Alkaloids through Biomimetic Synthetic Way

  • Le, Thanh Nguyen (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Cho, Won-Jea (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
  • Published : 2006.12.20

Abstract

Keywords

References

  1. Mackay, S. P.; Meth-Cohn, O.; Waich, R. D. In Advances in Heterocyclic Chemistry; Academic Press: Orlando, 1997; Vol. 67
  2. Simanek, V. The Alkaloids; Academic Press: Orlando, 1985; Vol. 26
  3. Lee, Y. S.; Kim, W. S.; Kim, K. H.; Yoon, M. J.; Cho, H. J.; Shen, Y.; Ye, J. M.; Lee, C. H.; Oh, W. K.; Kim, C. T.; Hohnen-Behrens, C.; Gosby, A.; Kraegen, E. W.; James, D. E.; Kim, J. B. Diabetes 2006, 55, 2256 https://doi.org/10.2337/db06-0006
  4. Lin, C. C.; Kao, S. T.; Chen, G. W.; Chung, J. G. Anticancer 2005, 25, 4149
  5. Letasiova, S.; Jantova, S.; Cipak, L.; Muckova, M. Cancer Lett. 2006, 239, 254 https://doi.org/10.1016/j.canlet.2005.08.024
  6. Yu, H. H.; Kim, K. J.; Cha, J. D.; Kim, H. K.; Lee, Y. E.; Choi, N. Y.; You, Y. O. J. Med. Food 2005, 8, 454 https://doi.org/10.1089/jmf.2005.8.454
  7. Hwang, J. M.; Kuo, H. C.; Tseng, T. H.; Liu, J. Y.; Chu, C. Y. Arch. Toxicol. 2006, 80, 62 https://doi.org/10.1007/s00204-005-0014-8
  8. Cho, B. J.; Im, E. K.; Kwon, J. H.; Lee, K. H.; Shin, H. J.; Oh, J.; Kang, S. M.; Chung, J. H.; Jang, Y. Mol. Cells 2005, 20, 429
  9. Kong, W.; Wei, J.; Abidi, P.; Lin, M.; Inaba, S.; Li, C.; Wang, Y.; Wang, Z.; Si, S.; Pan, H.; Wang, S.; Wu, J.; Wang, Y.; Li, Z.; Liu, J.; Jiang, J. D. Nat. Med. 2004, 10, 1344 https://doi.org/10.1038/nm1135
  10. Kemeny-Beke, A.; Aradi, J.; Damjanovich, J.; Beck, Z.; Facsko, A.; Berta, A.; Bodnar, A. Cancer Lett. 2006, 237, 67 https://doi.org/10.1016/j.canlet.2005.05.037
  11. Hoffmann, T. K.; Leenen, K.; Hafner, D.; Balz, V.; Gerharz, C. D.; Grund, A.; Ballo, H.; Hauser, U.; Bier, H. Anticancer Drugs 2002, 13, 93 https://doi.org/10.1097/00001813-200201000-00011
  12. Lou, H.; Ookhtens, M.; Stolz, A.; Kaplowitz, N. Am. J. Physiol. Gastrointest Liver Physiol. 2003, 285, G1335 https://doi.org/10.1152/ajpgi.00271.2003
  13. Ishikawa, T.; Ishii, H. Heterocycles 1999, 50, 627 https://doi.org/10.3987/REV-98-SR(H)9
  14. Clement, B.; Weide, M.; Wolschendorf, U.; Kock, I. Angew. Chem. Int. Ed. 2005, 44, 635 https://doi.org/10.1002/anie.200461969
  15. Le, T. N.; Gang, S. G.; Cho, W. J. J. Org. Chem. 2004, 69, 2768 https://doi.org/10.1021/jo035836+
  16. Le, T. N.; Gang, S. G.; Cho, W. J. Tetrahedron Lett. 2004, 45, 2763 https://doi.org/10.1016/j.tetlet.2004.02.031
  17. Takao, N.; Kamigauchi, M.; Okada, M. Helv. Chim. Acta 1983, 66, 473 https://doi.org/10.1002/hlca.19830660208
  18. Cho, W. J.; Kim, E. K.; Park, I. Y.; Jeong, E. Y.; Kim, T. S.; Le, T. N.; Kim, D. D.; Lee, E. S. Bioorg. Med. Chem. 2002, 10, 2953 https://doi.org/10.1016/S0968-0896(02)00137-2
  19. Cho, W. J.; Min, S. Y.; Le, T. N.; Kim, T. S. Bioorg. Med. Chem. Lett. 2003, 13, 4451 https://doi.org/10.1016/j.bmcl.2003.09.001
  20. Cho, W. J.; Park, M. J.; Chung, B. H.; Lee, C. O. Bioorg. Med. Chem. Lett. 1998, 8, 41 https://doi.org/10.1016/S0960-894X(97)10190-1
  21. Poindexter, G. S. J. Org. Chem. 1982, 47, 3787 https://doi.org/10.1021/jo00140a047
  22. Le, T. N.; Cho, W. J. Chem. Pharm. Bull. 2005, 53, 118 https://doi.org/10.1248/cpb.53.118
  23. Hanaoka, M.; Motonishi, T.; Mukai, C. J. Chem. Soc., Perkin Trans. 1 1986, 2253

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