Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Biological Evaluation of Decursin, Prantschimgin and Their Derivatives

  • Xia, Yan (Molecular Cancer Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Min, Kyung-Hoon (College of Pharmacy, Chung-Ang University) ;
  • Lee, Kyeong (Molecular Cancer Research Center, Korea Research Institute of Bioscience and Biotechnology)
  • Published : 2009.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

The synthesis of coumarin-based natural products and their derivatives is described. In vitro MDR reversal activities of the synthesized compounds were evaluated in P-glycoprotein over-expressing human sarcoma cell line MES-SA/DX5. Some of the coumarin derivatives were found to show potent MDR reversal activity. In particular, pyridyl derivative (15e) exhibited more potency than verapamil.

Keywords

References

  1. Fylaktakidou, K. C.; Hadjipavlou.Litina, D. J.; Litinas, K. E.; Nicolaides, D. N. Curr. Pharm. Des. 2004, 10, 3813. https://doi.org/10.2174/1381612043382710
  2. Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Curr. Med. Chem. 2006, 13, 199. https://doi.org/10.1007/BF02977358
  3. Jeong, H. G.; Lee, J. H.; Jung, S. H.; Han, E. H.; Kim, J. H.; Kim, D. H.; Jin, M.; Siripuram, P. K.; Choi, Y.; Song, G. Y. Bull. Korean Chem. Soc. 2007, 28, 1725. https://doi.org/10.1007/BF02976682
  4. Lee, S. U.; Park, J. H.; Kwon, T. H.; Yoo, Y. J.; Lee, J. Y.; Shin, C. G.; Yoo, K. H.; Lee, Y. S. Bull. Korean Chem. Soc. 2007, 28, 1510. https://doi.org/10.1016/j.fitote.2006.09.005
  5. Kang, S. Y.; Kim, Y. C. Arch. Pharm. Res. 2007, 30, 1368 https://doi.org/10.1007/BF02976860
  6. Lee, S.; Lee, Y. S.; Jung, S. H.; Shin, K. H.; Kim, B. K.; Kang, S. S. Arch. Pharm. Res. 2003, 26, 727 https://doi.org/10.1007/BF02976681
  7. Lima, V.; Silva, C. B.; Mafezoli, J.; Bezerra, M. M.; Moraes, M. O.; Mourao, G. S.; Silva, J. N.; Oliveira, M. C. Fitoterapia. 2006, 77, 574 https://doi.org/10.1055/s-2006-957701
  8. Lee, S.; Shin, D. S.; Kim, J. S.; Oh, K. B.; Kang, S. S. Arch. Pharm. Res. 2003, 26, 449 https://doi.org/10.1186/bcr1790
  9. Lee, Y. Y.; Lee, S.; Jin, J. L.; Yun.Choi, H. S. Arch. Pharm. Res. 2003, 26, 723 https://doi.org/10.1016/S0040-4020(03)00861-5
  10. Ahn, K. S.; Sim, W. S.; Lee, I. K.; Seu, Y. B.; Kim, I. H. Planta Med. 1997, 63, 360 https://doi.org/10.1038/nrd1984
  11. Jiang, C.; Guo, J.; Wang, Z.; Xiao, B.; Lee, H. J.; Lee, E. O.; Kim, S. H.; Lu, J. Breast Cancer Res. 2007, 9, R77. https://doi.org/10.1021/ja994209s
  12. Song, G. Y.; Lee, J. H.; Cho, M.; Park, B. S.; Kim, D. E.; Oh, S. Mol. Pharmacol. 2007, 72, 1599. https://doi.org/10.1124/mol.107.040253
  13. Yim, D.; Singh, R. P.; Agarwal, C.; Lee, S.; Chi, H.; Agarwal, R. Cancer Res. 2005, 65, 1035.
  14. Bae, E. A.; Han, M. J.; Kim, N. J.; Kim, D. H. Biol. Pharm. Bull. 1998, 21, 990. https://doi.org/10.1248/bpb.21.990
  15. Tetsuhiro, N.; Takashi, O.; Masakatsu, S. Tetrahedron 2003, 59, 6889 https://doi.org/10.1016/S0040-4020(03)00861-5
  16. Szakacs, G.; Paterson, J. K.; Ludwig, J. A.; Booth.Genthe, C.; Gottesman, M. M. Nat. Rev. Drug Discov. 2006, 5, 219. https://doi.org/10.1038/nrd1984
  17. Modok, S.; Mellor, H. R.; Callaghan, R. Curr. Opin. Pharmacol. 2006, 6, 350. https://doi.org/10.1016/j.coph.2006.01.009
  18. Ozben, T. FEBS Lett. 2006, 580, 2903. https://doi.org/10.1016/j.febslet.2006.02.020
  19. Longley, D. B.; Johnston, P. G. J. Pathol. 2005, 205, 275. https://doi.org/10.1002/path.1706
  20. Ryan, W.; Van, D. W.; Derek, J.; Magdziak, J. N.; Thomas, R.; Pettus, R. J. Am. Chem. Soc. 2000, 122, 6502 https://doi.org/10.1021/ja994209s
  21. Cornwell, M. M.; Pastan, I.; Gottesman, M. M. J. Biol. Chem. 1987, 262, 2166

Cited by

  1. Synthesis and Biological Evaluation of Phenoxy-N-phenylacetamide Derivatives as Novel P-glycoprotein Inhibitors vol.32, pp.10, 2011, https://doi.org/10.5012/bkcs.2011.32.10.3666
  2. ChemInform Abstract: Synthesis and Biological Evaluation of Decursin (IIb), Prantschimgin (Ib) and Their Derivatives. vol.40, pp.28, 2009, https://doi.org/10.1002/chin.200928192
  3. Discovery of Highly Potent Multidrug Resistance (MDR) Reversal Agents: Aminosulfonylaryl Isoxazole Derivatives vol.30, pp.4, 2009, https://doi.org/10.5012/bkcs.2009.30.4.779
  4. Targeting Multidrug Resistance with Small Molecules for Cancer Therapy vol.18, pp.4, 2009, https://doi.org/10.4062/biomolther.2010.18.4.375
  5. Analysis of plant-derived phytochemicals as anti-cancer agents targeting cyclin dependent kinase-2, human topoisomerase IIa and vascular endothelial growth factor receptor-2 vol.41, pp.3, 2009, https://doi.org/10.1080/10799893.2020.1805628