Bulletin of the Korean Chemical Society

  • 제25권12호
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  • Pages.1784-1790
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  • 2004
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of Tetrahydrocarbazole Derivatives as Potent β3-Adrenoceptor Agonists

  • Ha, Jae-Du (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Kang, Seung-Kyu (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Cheon, Hyae-Gyeong (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • Choi, Joong-Kwon (Medicinal Science Division, Korea Research Institute of Chemical Technology)
  • 발행 : 2004.12.20
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초록

A series of 2-(3-chlorophenyl)-2-hydroxyethylamine derivatives containing a tetrahydrocarbazole linker were prepared and evaluated for their ${\beta}_3$-adrenoceptor agonistic activity. Several compounds showed potency comparable to CL-316243.

키워드

참고문헌

  1. Lands, A. M.; Arnold, A.; McAuliff, J. P.; Luduena, F. P.;Brown, T. G., Jr. Nature 1967, 214, 597. https://doi.org/10.1038/214597a0
  2. Strosberg, A. D.Annu. Rew. Pharmacol. Toxicol. 1997, 37, 421. https://doi.org/10.1146/annurev.pharmtox.37.1.421
  3. Arch, T. G. S. Proc. Nutrition Soc. 1989, 48, 215. https://doi.org/10.1079/PNS19890032
  4. Emorine,L. J.; Marullo, S.; Briend-Sutren, M.-M.; Patey, G.; Tate, K.;Delavier-Klutchko, C.; Strosberg, A. D. Science 1989, 245, 1118. https://doi.org/10.1126/science.2570461
  5. Tan, S.; Curtis-Prior, P. B. Int. J. Obesity 1983, 7, 409.
  6. Lafonate, M.; Berlan, M. J. Lipid Res. 1993, 34, 1057.
  7. Weyer, C.; Gautier, J. F.; Danforth, E., Jr. Diabetes Metab.1999, 25, 11.
  8. Souza, J. C.; Burkey, B. F. Curr. Pharm. Des.2001, 7, 1433. https://doi.org/10.2174/1381612013397339
  9. Weber, A. E. Annu. Rep. Med. Chem. 1998, 33,193. https://doi.org/10.1016/S0065-7743(08)61084-2
  10. Cantello, B. C. C.; Smith, S. A. Drugs Future 1991, 16, 797.
  11. Sher, P. M.; Fisher, L. G.; Skwish, S.; Michel, I. M.; Seiler, S.M.; Washburn, W. N.; Dickinson, K. E. J. Med. Chem. Res. 1997,7, 109.
  12. Bloom, J. D.; Dutia, M. D.; Johnson, B. D.; Wissner, A.; Burns, M. G.; Largis, E. E.; Dolan, J. A.; Claus, T. H. J. Med. Chem.1992, 35, 3081. https://doi.org/10.1021/jm00094a025
  13. Harada, H.; Hirokawa, Y.; Suzuki, K.; Hiyama, Y.; Oue, M.;Kawashima, H.; Yoshida, N.; Furutani, Y.; Kato, S. Bioorg. Med.Chem. Lett. 2003, 13, 1301. https://doi.org/10.1016/S0960-894X(03)00073-8
  14. Cecchi, R.; Croci, T.; Boigegrain, R.; Boveri, S.; Baroni, M.;Boccardi, G.; Guimbard, J. P.; Guzzi, U. Eur. J. Med. Chem. 1994,29, 259. https://doi.org/10.1016/0223-5234(94)90095-7
  15. Badone, D.; Guzzi, U. Bioorg. Med. Chem. Lett.1994, 4, 1921. https://doi.org/10.1016/S0960-894X(01)80535-7
  16. Cooke, J. W. B.; Glover, B. N.; Lawrence, R. M.; Sharp, M. J.;Timoschenko, M. F. WO 0266418, April 15, 2003.
  17. Yanai, M.; Kawamura, K.; Ueno, M.; Hiramoto, S.; Katsuyama,K.; Fuchizawa, S.; Takahashi, T. 220th ACS Natl. Meet.(Washington DC), Abst. MEDI 303, 2000.
  18. Hieble, J. P.; Bondinell, W. E.; Ruffolo, R. R., Jr. J. Med.Chem. 1995, 38, 3415. https://doi.org/10.1021/jm00018a001
  19. Kordik, C. P.; Reitz, A. B. J. Med.Chem. 1999, 42, 181. https://doi.org/10.1021/jm980521l
  20. Kang, S. K.; Ha, J. D.; Cheon, H.-G.; Choi, J.-K.; Hong, C. S.;Yum, E. K. Bull. Korean Chem. Soc. 2003, 24, 1381. https://doi.org/10.5012/bkcs.2003.24.9.1381
  21. Ok, H.O.; Reigle, L. B.; Candelore, M. A.; Colwell, L. F.; Deng, L.;Feeney, W. P. F.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.;Strader, C. D.; Tota, L.; Wang, M. J.; Wyvratt, M. J.; Fisher, M.H.; Weber, A. E. Bioorg. Med. Chem. Lett. 2000, 10, 1531. https://doi.org/10.1016/S0960-894X(00)00277-8
  22. Rogers, C. U.; Corson, B. B. J. Am. Chem. Soc. 1947, 69,2911. https://doi.org/10.1021/ja01203a507
  23. Edwards, J. P.; West, S. J.; Pooley, C. L. F.; Marschke,K. B.; Farmer, L. J.; Jones, T. K. Bioorg. Med. Chem. Lett. 1998,8, 745. https://doi.org/10.1016/S0960-894X(98)00107-3
  24. Fisher, M. H.; Amend, A. M.; Bach, T. J.; Baker, J. M.; Brady, E.J.; Candelore, M. R.; Carroll, D.; Cascieri, M. A.; Chiu, S.-H. L.;Deng, L.; Forrest, M. J.; Hegarty-Friscino, B.; Guan, X.-M.; Hom,G. J.; Hutchins, J. E.; Kelly, L. J.; Mathvik, R. J.; Metzger, J. M.;Miller, R. R.; Ok, H. O.; Parmee, E. R.; Saperstein, R.; Strader, C.D.; Stearns, R. A.; Thompson, G. M.; Tota, L.; Vicario, P. P.;Weber, A. E.; Woods, J. W.; Wyvratt, M. J.; Zafian, P. T.;MacIntyre, D. E. J. Clin. Invest. 1998, 101, 2387. https://doi.org/10.1172/JCI2496
  25. Yang, S. D.; Rhee, S. D. unpulished results

피인용 문헌

  1. Aerobic C–H amination of tetrahydrocarbazole derivatives via photochemically generated hydroperoxides vol.11, pp.27, 2013, https://doi.org/10.1039/c3ob40919h
  2. Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review vol.20, pp.8, 2015, https://doi.org/10.3390/molecules200813496
  3. New syntheses of cycloalka[b]indoles vol.52, pp.9, 2016, https://doi.org/10.1134/S1070428016090013
  4. Synthesis of Tetrahydrocarbazole Derivatives as Potent ?3-Adrenoceptor Agonists. vol.36, pp.21, 2005, https://doi.org/10.1002/chin.200521123
  5. Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290 vol.83, pp.1, 2009, https://doi.org/10.1007/s00253-008-1853-z
  6. Design and Synthesis of Novel Epidermal Growth Factor Receptor Kinase Inhibitors vol.26, pp.6, 2005, https://doi.org/10.5012/bkcs.2005.26.6.959