Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and COX Inhibitory Activities of Rutaecarpine Derivatives

  • Published : 2005.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

A series of substituted rutaecarpines were prepared by employing Fischer indole synthesis as key step and their inhibitory activities on COX-1 and 2 as well as selectivity on COX-2 were evaluated. The compounds with a methanesulfonyl and a bromo group at C10 showed promising inhibitory activity ($IC_{50}$ = 0.27, 0.35 $\mu$M, respectively) with selectivity.

Keywords

References

  1. Yashima, Y.; Kashiwaki, K. J. Pharm. Soc., Jpn. 1915, 35, 1293
  2. Chu, J. H. Science Record (China) 1951, 4, 279
  3. Chu, J. H. Science Record (China) 1951, 4, 279 (Chem. Abstr. 1952, 46, 11589b)
  4. Li, H. T.; Hong, H.-I. Yao Hseun Pao 1966, 13, 265
  5. Li, H. T.; Hong, H.-I. (Chem. Abstr. 1966, 65, 3922c)
  6. Moon, T. C.; Murakami, M.; Kudo, I.; Son, K. H.; Kim, H. P.; Kang, S. S.; Chang, H. W. Inflamm. Res. 1999, 48, 621 https://doi.org/10.1007/s000110050512
  7. Chiou, W. F.; Chou, C. J.; Liao, J. F.; Sham, A. Y.; Chen, C. F. Eur. J. Pharmacol. 1994, 257, 59 https://doi.org/10.1016/0014-2999(94)90694-7
  8. Wang, G. J.; Wu, X. C.; Chen, C. F.; Lin, L. C.; Huang, Y. T.; Shan, J.; Pang, P. K. J. Pharmacol. Exp. Ther. 1999, 289, 1237
  9. Kong, Y. C.; Hu, H. A.; Lau, F. K.; Che, C. T.; Yeng, H. W.; Cheng, S.; Hwang, C. C. Am. J. Chin. Med. 1976, 4, 105 https://doi.org/10.1142/S0192415X76000160
  10. Sheen, W. S.; Tsai, I. L.; Teng, C. M.; Ko, F. N.; Chen, I. S. Planta Med. 1996, 62, 175 https://doi.org/10.1055/s-2006-957846
  11. Yamahara, J.; Yamada, T.; Kitani, T.; Oh, Y. N.; Fujimura, H. Chem. Pharm. Bull. 1989, 37, 1820 https://doi.org/10.1248/cpb.37.1820
  12. Yang, L.-M.; Chen, C.-F.; Lee, K.-H. Biorg. Med. Chem. Lett. 1995, 5, 465
  13. Yashima, Y.; Manske, R. H. F.; Robinson, R. J. Chem. Soc. 1927, 1708 https://doi.org/10.1039/jr9270001708
  14. Schopf, C. Angew. Chem. 1937, 50, 779 https://doi.org/10.1002/ange.19370504002
  15. Schopf, C. Angew. Chem. 1937, 50, 797 https://doi.org/10.1002/ange.19370504103
  16. Schopf, C.; Steuer, H. Ann. 1947, 558, 124
  17. Yamazaki, M.; Ikuba, A. Tetrahedron Lett. 1966, 3221
  18. Fitzgerald, J. S.; Johns, S. R.; Lamberton, J. A.; Redcliff, A. H. Aust. J. Chem. 1966, 19, 151 https://doi.org/10.1071/CH9660151
  19. Yamazaki, M.; Ikuta, A.; Mori, T.; Kawana, T. Tetrahedron Lett. 1967, 28, 3317
  20. Kametani, T.; Higa, T.; Fukumoto, K.; Koizumi, M. Heterocycles 1976, 4, 23 https://doi.org/10.3987/R-1976-01-0023
  21. Kametani, T.; Higa, T.; Loc, C. V.; Ihara, M.; Koizumi, C. V.; Fukumoto, K. J. Am. Chem. Soc. 1976, 98, 6186 https://doi.org/10.1021/ja00436a019
  22. Kametani, T.; Loc, C. V.; Higa, T.; Koizumi, M.; Ihara, M.; Fukumoto, M. J. Am. Chem. Soc. 1977, 99, 2306 https://doi.org/10.1021/ja00449a047
  23. Mohrle, H.; Kamper, C.; Schmid, R. Arch. Pharm. 1980, 313, 990 https://doi.org/10.1002/ardp.19803131204
  24. Bergman, T. J.; Bergman, S. Heterocycles 1981, 16, 347 https://doi.org/10.3987/R-1981-03-0347
  25. Kokosi, J.; Hermecz, I.; Szasz, G.; Meszaros, Z. Tetrahedron Lett. 1981, 22, 4861 https://doi.org/10.1016/S0040-4039(01)92365-2
  26. Kokosi, J.; Szasz, G.; Hermecz, I. Tetrahedron Lett. 1992, 33, 2995 https://doi.org/10.1016/S0040-4039(00)79581-5
  27. Eguchi, S.; Takeuchi, H.; Matsushita, Y. Heterocycles 1992, 33, 153 https://doi.org/10.3987/COM-91-S62
  28. Lee, S. H.; Kim, S. I.; Park, J. G.; Lee, E. S.; Jahng, Y. Heterocycles 2001, 55, 1555 https://doi.org/10.3987/COM-01-9244
  29. Mohanta, P. K.; Kim, K. Tetrahedron Lett. 2002, 43, 3993 https://doi.org/10.1016/S0040-4039(02)00711-6
  30. Lee, E. S.; Park, J. G.; Jahng, Y. Tetrahedron Lett. 2003, 44, 1883 https://doi.org/10.1016/S0040-4039(03)00080-7
  31. Chavan, S. P.; Sivappa, R. Tetrahedron Lett. 2004, 45, 997 https://doi.org/10.1016/j.tetlet.2003.11.090
  32. Mhaske, S. B.; Argade, N. P. Tetrahedron 2004, 60, 3417 https://doi.org/10.1016/j.tet.2004.02.037
  33. Harayama, T.; Hori, A.; Servan, G.; Morikami, Y.; Matsumoto, T.; Abe, H.; Takeuchi, Y. Tetrahedron 2004, 60, 10645
  34. For review see: Bergman, J. In Alkaloids: Brossi, A., Ed.; Academic Press: New York, 1985; pp 30-54
  35. Baruah, B.; Dasu, K.; Vaitilingam, B.; Mamnoor, P.; Venkata, P. P.; Rajagopal, S.; Yeleswarapu, K. R. Biorg. Med. Chem. Lett. 2004, 12, 1991 https://doi.org/10.1016/j.bmc.2004.03.005
  36. Chang, H. W.; Kim, S. I.; Jung, H.; Jahng, Y. Heterocycles 2003, 60, 1359 https://doi.org/10.3987/COM-03-9744
  37. v. Konigs, E.; Wylezich, A. J. Prakt. Chem. 1931, 24

Cited by

  1. Progress in the Studies on Rutaecarpine vol.13, pp.2, 2008, https://doi.org/10.3390/molecules13020272
  2. Alkaloid Analogues vol.15, pp.7, 2013, https://doi.org/10.1021/co400055b
  3. Pyrrole and Fused Pyrrole Compounds with Bioactivity against Inflammatory Mediators vol.22, pp.3, 2017, https://doi.org/10.3390/molecules22030461
  4. Synthesis and COX Inhibitory Activities of Rutaecarpine Derivatives. vol.37, pp.16, 2005, https://doi.org/10.1002/chin.200616158
  5. A Facile Synthesis of Mollugin vol.28, pp.10, 2005, https://doi.org/10.5012/bkcs.2007.28.10.1863
  6. Quinoline, quinazoline and acridone alkaloids vol.25, pp.1, 2005, https://doi.org/10.1039/b612168n
  7. Synthesis and Biological Properties of Benzo-Annulated Rutaecarpines vol.33, pp.10, 2005, https://doi.org/10.1248/bpb.33.1704
  8. Cardiovascular Pharmacological Actions of Rutaecarpine, a Quinazolinocarboline Alkaloid Isolated From Evodia rutaecarpa vol.3, pp.2, 2005, https://doi.org/10.1016/j.jecm.2011.02.004
  9. RhII2‐Catalyzed Synthesis of α‐, β‐, or δ‐Carbolines from Aryl Azides vol.124, pp.24, 2005, https://doi.org/10.1002/ange.201201788
  10. RhII2‐Catalyzed Synthesis of α‐, β‐, or δ‐Carbolines from Aryl Azides vol.51, pp.24, 2005, https://doi.org/10.1002/anie.201201788
  11. Synthesis, potential anti-inflammatory and analgesic activities study of (S)-N-substituted-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamides vol.27, pp.15, 2005, https://doi.org/10.1016/j.bmcl.2017.06.002
  12. Exceedingly Fast, Direct Access to Dihydroisoquinolino[1,2-b]quinazolinones through a Ruthenium(II)-Catalyzed Redox-Neutral C-H Allylation/Hydroamination Cascade vol.20, pp.22, 2005, https://doi.org/10.1021/acs.orglett.8b03048