DOI QR코드

DOI QR Code

Facile Synthesis of Mollugin by Kinetic Control and anti-HCV (Hepatitis C Virus) Activity of Its Analogues

  • Choi, Da Hye (Department of Chemistry and Institute of Applied Chemistry, Hallym University) ;
  • Lee, Na Ri (Department of Chemistry and Institute of Applied Chemistry, Hallym University) ;
  • Kim, Cheol Gi (Department of Chemistry and Institute of Applied Chemistry, Hallym University) ;
  • Kim, Jong Woo (Advanced Institutes of Convergence Technology, B&C Biopharm Co. Ltd.) ;
  • Lee, Sang Wook (Advanced Institutes of Convergence Technology, B&C Biopharm Co. Ltd.) ;
  • Jun, Jong-Gab (Department of Chemistry and Institute of Applied Chemistry, Hallym University)
  • Received : 2014.05.08
  • Accepted : 2014.07.15
  • Published : 2014.11.20

Abstract

Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.

Keywords

References

  1. (a) Schildknecht, H.; Straub, F.; Scheidel, V. Liebigs Ann. Chem. 1976, 1295.
  2. (b) Itokawa, H.; Mihara, K.; Takeya, K. Chem. Pharm. Bull. 1983, 31, 2353. https://doi.org/10.1248/cpb.31.2353
  3. (c) Itokawa, H.; Qiao, Y.; Takeya, K. Phytochemistry 1989, 28, 3465. https://doi.org/10.1016/0031-9422(89)80365-6
  4. (d) Ozgen, U.; Kazaz, C.; Secen, H.; Coskun, M. Turk J. Chem. 2006, 30, 15.
  5. Itokawa, H.; Watanabe, K.; Mihara, K.; Takeya, K. Shoyakugaku Zasshi 1982, 36, 145.
  6. Ho, L.-K.; Don, M.-J.; Chen, H.-C.; Yeh, S.-F.; Chen, J.-M. J. Nat. Prod. 1996, 59, 330. https://doi.org/10.1021/np960200h
  7. Murase, T.; Hase, T.; Shibuya, Y.; Nishizawa, Y.; Tokimitsu, I. PCT Int. Appl. 1997, WO 9735557 A1.
  8. Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67, 127. https://doi.org/10.1055/s-2001-11498
  9. Schildknecht, H.; Straub, F. Liebigs Ann. Chem. 1976, 1307.
  10. (a) Heide, L.; Leistner, E. J. Chem. Soc., Chem. Comm. 1981, 334.
  11. (b) Ho, L.-K.; Yu, H.-J.; Ho, C.-T.; Don, M.-J. J. Chin. Chem. Soc. 2001, 48, 77. https://doi.org/10.1002/jccs.200100014
  12. (c) Lumb, J.-P.; Trauner, D. Org. Lett. 2005, 7, 5865. https://doi.org/10.1021/ol052472u
  13. (d) Habonimana, P.; Claessens, S.; De Kimpe, N. Synlett. 2006, 2472.
  14. (e) Claessens, S.; Kesteleyn, B.; Van, T. N.; De Kimpe, N. Tetrahedron 2006, 62, 8419. https://doi.org/10.1016/j.tet.2006.06.014
  15. (f) Lee, Y. R.; Wang, X.; Kim, Y. M.; Shim, J. J.; Kim, B. N.; Han, D. H. Bull. Korean Chem. Soc. 2007, 28, 1735. https://doi.org/10.5012/bkcs.2007.28.10.1735
  16. (g) Jung, H. W.; Oh, J. S.; Lee, S. H.; Liang, J. L.; Kim, D. H.; Motiur Rahman, A. F. M.; Jahng, Y. Bull. Korean Chem. Soc. 2007, 28, 1863. https://doi.org/10.5012/bkcs.2007.28.10.1863
  17. (a) Nicolaou, K. C.; Liu, J. J.; Hwang, C. K.; Dai, W. M.; Guy, R. K. J. Chem. Soc., Chem. Comm. 1992, 1118.
  18. (b) Pettigrew, J. D.; Cadieux, J.-A.; So, S. S. S.; Wilson, P. D. Org. Lett. 2005, 7, 467. https://doi.org/10.1021/ol047578o
  19. (c) Lee, J.-H.; Bang, H. B.; Han, S. Y.; Jun, J.-G. Tetrahedron Lett. 2007, 48, 2889. https://doi.org/10.1016/j.tetlet.2007.02.088
  20. Velmurugan, D.; Malar Selvi, U.; Mythily, U.; Rao, K.; Rajarajeshwari, R.; S. Curr. Bioinform. 2012, 7, 187. https://doi.org/10.2174/157489312800604462
  21. Rosen, H. R. N. Engl. J. Med. 2011, 364, 2429. https://doi.org/10.1056/NEJMcp1006613
  22. Kim, J. W.; Lee, S. W.; Han, J. J.; Park, S. J.; Shin, J. C.; Yang, J. W.; Lee, Y. C.; Park, B. K. PCT/KR2010/000376, WO 2010/085091 A2.
  23. Fattovich, G.; Stroffolini, T.; Zagni, I.; Donato, F. Gastroenterology 2004, 127, S35. https://doi.org/10.1053/j.gastro.2004.09.014
  24. Awad, T.; Thorlund, K.; Hauser, G.; Stimac, D.; Mabrouk, M.; Gluud, C. Hepatology 2010, 51, 1176. https://doi.org/10.1002/hep.23504
  25. Liang, T. J.; Ghany, M. G. N. Engl. J. Med. 2013, 368, 1907. https://doi.org/10.1056/NEJMra1213651
  26. Liu, J.; Manheimer, E.; Tsutani, K.; Gluud, C. Am. J. Gastroenterol. 2003, 98, 538. https://doi.org/10.1111/j.1572-0241.2003.07298.x
  27. (a) Itokawa, H.; Ibraheim, Z. Z.; Qiao, Y. F.; Takeya, K. Chem. Pharm. Bull. 1993, 41, 1869. https://doi.org/10.1248/cpb.41.1869
  28. (b) El-Hady, S.; Bukuru, J.; Kesteleyn, B.; Van Puyvelde, L.; Nguyen, V. T.; De Kimpe, N. J. Nat. Prod. 2002, 65, 1377. https://doi.org/10.1021/np020110e
  29. (c) Mudiganti, N. V. S.; Claessens, S.; Habonimana, P.; De Kimpe, N. J. Org. Chem. 2010, 75, 2274. https://doi.org/10.1021/jo100024b
  30. Mudiganti, N. V. S.; Claessens, S.; De Kimpe, N. Tetrahedron Lett. 2008, 49, 6980 https://doi.org/10.1016/j.tetlet.2008.09.138
  31. (a) Helesbeux, J.-J.; Duval, O.; Guilet, D.; Seraphin, D.; Rondeau, D.; Richomme, P. Tetrahedron 2003, 59, 5091. https://doi.org/10.1016/S0040-4020(03)00733-6
  32. (b) Madabhushi, S.; Jillella, R.; Godala, K. R.; Mallu, K. K. R.; Beeram, C. R.; Chintala, N. Tetrahedron Lett. 2012, 53, 5275. https://doi.org/10.1016/j.tetlet.2012.07.077
  33. Chen, W.-L.; Li, J.; Zhu, Y.-H.; Ye, L.-T.; Hu, W.; Mo, W. M. ARKIVOC 2011, (ix), 381.
  34. Gilead Sciences ClinicalTrials.gov Identifier: NCT01072695.

Cited by

  1. ring contraction and C–O scission strategy vol.20, pp.15, 2018, https://doi.org/10.1039/C8GC00749G