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Synthetic Approaches to Natural Antioxidant Benzastatin E, F and G Analogues

  • Le, Thanh Nguyen (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Yang, Su-Hui (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Khadka, Daulat Bikram (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Cho, Suk-Hee (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Zhao, Chao (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)
  • Received : 2011.09.16
  • Accepted : 2011.10.13
  • Published : 2011.12.20

Abstract

For synthesis of benzastatin E, F and G analogues, the indole-2-carbaldehydes with or without substituents at C-5 position were prepared as key intermediates. Several synthetic attempts to achieve benzastatin E-G analogues were suggested using the indole-2-carbaldehyde intermediates.

Keywords

References

  1. Choi, D. W. J. Neurosci. 1990, 10, 2493.
  2. Kinouchi, H.; Epstein, C. J.; Mizui, T.; Carlson, E.; Chen, S. F.; Chan, P. H. Proc. Natl. Acad. Sci. USA 1991, 88, 11158. https://doi.org/10.1073/pnas.88.24.11158
  3. Jacobsen, E. J.; VanDoornik, F. J.; Ayer, D. E.; Belonga, K. L.; Braughler, J. M.; Hall, E. D.; Houser, D. J. J. Med. Chem. 1992, 35, 4464. https://doi.org/10.1021/jm00101a025
  4. Coyle, J. T.; Puttfarcken, P. Science 1993, 262, 689. https://doi.org/10.1126/science.7901908
  5. Kim, W. G.; Kim, J. P.; Kim, C. J.; Lee, K. H.; Yoo, I. D. J. Antibiot. 1996, 49, 20. https://doi.org/10.7164/antibiotics.49.20
  6. Kim, W. G.; Kim, J. P.; Yoo, I. D. J. Antibiot. 1996, 49, 26. https://doi.org/10.7164/antibiotics.49.26
  7. Kim, W. G.; Kim, J. P.; Koshino, H.; ShinYa, K.; Seto, H.; Yoo, I. D. Tetrahedron 1997, 53, 4309. https://doi.org/10.1016/S0040-4020(97)00157-9
  8. Kim, W. G.; Ryoo, I. J.; Park, J. S.; Yoo, I. D. J. Antibiot. 2001, 54, 513. https://doi.org/10.7164/antibiotics.54.513
  9. Toda, N.; Ori, M.; Takami, K.; Tago, K.; Kogen, H. Org. Lett. 2003, 5, 269. https://doi.org/10.1021/ol027215t
  10. Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Tetrahedron 2005, 61, 2075. https://doi.org/10.1016/j.tet.2004.12.041
  11. Mali, R. S.; Yadav, V. J. Synthesis 1984, 10, 862.
  12. Krahl, M. P.; Jager, A.; Krause, T.; Knolker, H. J. Org. Biomol. Chem. 2006, 4, 3215. https://doi.org/10.1039/b607792g
  13. Hawkins, G. F.; Roe, A. J. Org. Chem. 1949, 14, 328. https://doi.org/10.1021/jo01154a021
  14. Hansford, K. A.; Zanzarova, V.; Dorr, A.; Lubell, W. D. J. Comb. Chem. 2004, 6, 893. https://doi.org/10.1021/cc049904x
  15. Olah, G. A.; Narang, S. C.; Olah, J. A. Proc. Natl. Acad. Sci. USA 1981, 78, 3298. https://doi.org/10.1073/pnas.78.6.3298