Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Semisynthesis of Licochalcone E and Biological Evaluation as Vasorelaxant Agents

  • Yoon, Goo (Korea Institute of Science and Technology, Gangneung Institute) ;
  • Oak, Min-Ho (Research and Development Center, Hanwha Pharma. Co., Ltd.) ;
  • Lee, Jung-Ok (Research and Development Center, Hanwha Pharma. Co., Ltd.) ;
  • Cheon, Seung-Hoon (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
  • Published : 2010.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Furuya, T.; Matsumoto, K.; Hikichi, M. Tetrahedron Lett. 1971,12, 2567. https://doi.org/10.1016/S0040-4039(01)96921-7
  2. Saitoh, T.; Shibata, S. Tetrahedron Lett. 1975, 16, 4461. https://doi.org/10.1016/S0040-4039(00)91092-X
  3. Kajiyama, K.; Demizu, S.; Hiraga, Y.; Kinoshita, K.; Koyama, K.;Takahash, K.; Tamura, Y.; Okada, K.; Kinoshita, T. Phytochemistry1992, 31, 3229. https://doi.org/10.1016/0031-9422(92)83481-D
  4. Yoon, G.; Jung, Y. D.; Cheon, S. H. Chem. Pharm. Bull. 2005, 53,694. https://doi.org/10.1248/cpb.53.694
  5. Park, E. J.; Park, H. R.; Lee, J. S.; Kim, J. W. Planta Med. 1998,64, 464. https://doi.org/10.1055/s-2006-957485
  6. Shibata, S.; Inoue, H.; Iwata, S.; Ma, R.; Yu, L.; Ueyama, H.; Takayasu, J.; Hasegawa, T.; Tokuda, H.; Nishino, A.; Nishino,H.; Iwashima, A. Planta Med. 1991, 57, 221. https://doi.org/10.1055/s-2006-960078
  7. Nomura, T.; Fukai, T.; Hano, Y. In Studies in Natural ProductsChemistry; Atta-ur-Rahman, Ed.; Elsevier Science: London, 2003;Vol. 28, pp 199-256.
  8. Friis-Moller, A.; Chen, M.; Fuursted, K.; Christensen, S. B.; Kharazmi,A. Planta Med. 2002, 68, 416. https://doi.org/10.1055/s-2002-32087
  9. Nielsen, S. F.; Chen, M.; Theander, T. G.; Kharazmi, A.; Christensen,S. B. Bioorg. Med. Chem. Lett. 1995, 5, 449. https://doi.org/10.1016/0960-894X(95)00053-V
  10. Nielsen, S. F.; Christensen, S. B.; Cruciani, G.; Kharazmi, A.;Liljefors, T. J. Med. Chem. 1998, 41, 4819. https://doi.org/10.1021/jm980410m
  11. Haraguchi, H.; Tanimoto, K.; Tamura, Y.; Mizutani, K.; Kinoshita,T. Phytochemistry 1998, 48, 125. https://doi.org/10.1016/S0031-9422(97)01105-9
  12. Haraguchi, H.; Ishikawa, H.; Mizutani, K.; Tamura, Y.; Kinoshita,T. Bioorg. Med. Chem. 1998, 6, 339. https://doi.org/10.1016/S0968-0896(97)10034-7
  13. Yoon, G.; Kang, B. Y.; Cheon, S. H. Arch Pharm. Res. 2007, 30,313. https://doi.org/10.1007/BF02977611
  14. Chang, H. J.; Yoon, G.; Park, J. S.; Kim, M. H.; Baek, M. K.; Kim,N. H.; Shin, B. A.; Ahn, B. W.; Cheon, S. H.; Jung, Y. D. Biol.Pharm. Bull. 2007, 30, 2290. https://doi.org/10.1248/bpb.30.2290
  15. Yoon, G.; Lee, W.; Kim, S. N.; Cheon, S. H. Bioorg. Med. Chem.Lett. 2009, 19, 5155. https://doi.org/10.1016/j.bmcl.2009.07.054
  16. Na, Y.; Cha, J. H.; Yoon, H. G.; Kwon, Y. Chem. Pharm. Bull.2009, 57, 607. https://doi.org/10.1248/cpb.57.607
  17. Yoon, G.; Liu, Z.; Jeong, H. J.; Cheon, S. H. Bull. Korean Chem.Soc. 2009, 30, 2959. https://doi.org/10.5012/bkcs.2009.30.12.2959
  18. Liu, Z.; Yoon, G.; Cheon, S. H. Tetrahedron Submitted.
  19. Roberts, R. M.; Landolt, R. G.; Greene, R. N.; Heyer, E. W. J. Am. Chem. Soc. 1967, 89, 1404. https://doi.org/10.1021/ja00982a023
  20. Conia, J. M.; LePerchec, P. Synthesis 1975, 1-19
  21. Marvell, E. N.; Anderson, D. R.; Ong, J. J. Org. Chem. 1962, 27,1109. https://doi.org/10.1021/jo01050a085
  22. Feletou, M.; Vanhoutte, P. M. Am. J. Physiol. Heart Circ. Physiol.2006, 291, H985. https://doi.org/10.1152/ajpheart.00292.2006
  23. Stoclet, J. C.; Chataigneau, T.; Ndiaye, M.; Oak, M. H.; El Bedoui,J.; Chataigneau, M.; Schini-Kerth, V. B. Eur. J. Pharmacol. 2004,500, 299. https://doi.org/10.1016/j.ejphar.2004.07.034
  24. Frankel, E. N.; Kanner, J.; German, J. B.; Parks, E.; Kinsella, J.E. Lancet 1993, 341, 454. https://doi.org/10.1016/0140-6736(93)90206-V
  25. Fitzpatrick, D. F.; Fleming, R. C.; Bing, B.; Maggi, D. A.; O'Malley,R. M. J. Agric. Food Chem. 2000, 48, 6384. https://doi.org/10.1021/jf0009347
  26. Sarr, M.; Chataigneau, M.; Martins, S.; Schott, C.; El Bedoui, J.;Oak, M. H.; Muller, B.; Chataigneau, T.; Schini-Kerth, V. B.Cardiovasc. Res. 2006, 71, 794. https://doi.org/10.1016/j.cardiores.2006.05.022

Cited by

  1. Molecular Modeling of Licochalcone E as Protein Tyrosine Phosphatase 1B Inhibitor vol.37, pp.12, 2016, https://doi.org/10.1002/bkcs.11032
  2. Highly Efficient Synthesis of Licochalcone E through Water-Accelerated [3,3]-Sigmatropic Rearrangement of Allyl Aryl Ether vol.32, pp.3, 2010, https://doi.org/10.5012/bkcs.2011.32.3.1059
  3. First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement vol.34, pp.1, 2013, https://doi.org/10.5012/bkcs.2013.34.1.54
  4. Synthetic methods and biological applications of retrochalcones isolated from the root of Glycyrrhiza species: A review vol.3, pp.None, 2010, https://doi.org/10.1016/j.rechem.2021.100216