Bulletin of the Korean Chemical Society

  • 제25권6호
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  • Pages.895-899
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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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The Syntheses of 3-Substituted 4-(Pyridin-2-ylthio)indoles via Leimgruber-Batcho Indole Synthesis

  • 발행 : 2004.06.20
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초록

We have designed a new family of radioligands, 3-(amino- and hydroxymethyl)-4-(5-iodopyridin-2-ylthio)indoles, combining characteristically distinct moieties proven to impart successful binding ability in a variety of structurally diverse selective serotonin reuptake inhibitors recently published. Described in this article are the syntheses of 3-substituted 4-(5-iodopyridin-2-ylthio)-indoles, featuring successful adaptation of the modified Leimgruber-Batcho indole synthesis onto the key intermediate 1-(5-iodopyridin-2-ylthio)-2-methyl-3-nitrobenzene (6) prepared from the nucleophilic aromatic substitution of chloropyridine 7 with thiophenol 8.

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참고문헌

  1. Owens, M. J.; Nemeroff, C. B. Clin. Chem. 1994, 40, 288-295.
  2. Hyttel, J. Int. Clin. Psychopharmacol. 1994, 1, 19-26.
  3. Frazer, A. J. Clin. Psychiatry 1997, 6, 9-25.
  4. Staley, J. K.; Malison, R. T.; Innis, R. B. Biol. Psychiatry 1998,44, 534-549. https://doi.org/10.1016/S0006-3223(98)00185-1
  5. Oh, S. J.; Ha, H.-J.; Chi, D. Y.; Lee, H. K. Current Med. Chem.2001, 8, 999-1034. https://doi.org/10.2174/0929867013372599
  6. Kim, J. Y.; Choe, H. K.; Choi, B. C.; Ha, H. J.; Oh, S. J. Bull.Korean Chem. Soc. 2003, 24, 1512-1514. https://doi.org/10.5012/bkcs.2003.24.10.1512
  7. Parsey, R. V.; Kegeles, L. S.; Hwang, D. R.; Simpson, N.; Abi-Dargham, A.; Mawlawi, O.; Slifstein, M.; Van Heertum, R. L.;Mann, J. J.; Laruelle, M. J. Nucl. Med. 2000, 41, 1465-1477.
  8. Mathis, C. A.; Taylor, S. E.; Biegon, A.; Enas, J. D. Brain Res.1993, 619, 229-235. https://doi.org/10.1016/0006-8993(93)91616-Z
  9. Biegon, A.; Mathis, C. A.; Hanrahan, S. M.; Jagust, W. J. BrainRes. 1993, 619, 236-246. https://doi.org/10.1016/0006-8993(93)91617-2
  10. Jagust, W. J.; Eberling, J. L.; Roberts, J. A.; Brennan, K. M.;Taylor, S. E.; Hanrahan, S. M.; VanBrocklin, H. F.; Enas, J. D.;Biegon, A.; Mathis, C. A. Eur. J. Pharmacol. 1993, 242, 189-193. https://doi.org/10.1016/0014-2999(93)90079-W
  11. Jagust, W. J.; Eberling, J. L.; Biegon, A.; Taylor, S. E.;VanBrocklin, H. F.; Jordan, S.; Hanrahan, S. M.; Roberts, J. A.;Brennan, K. M.; Mathis, C. A. J. Nucl. Med. 1996, 37, 1207-1214.
  12. Oya, S.; Choi, S. R.; Hou, C.; Mu, M.; Kung, M. P.; Acton, P. D.;Siciliano, M.; Kung, H. F. Nucl. Med. Biol. 2000, 27, 249-254. https://doi.org/10.1016/S0969-8051(00)00084-6
  13. Choi, S. R.; Hou, C.; Oya, S.; Mu, M.; Kung, M. P.; Siciliano, M.;Acton, P. D.; Kung, H. F. Synapse 2000, 38, 403-412. https://doi.org/10.1002/1098-2396(20001215)38:4<403::AID-SYN5>3.0.CO;2-Z
  14. Acton, P. D.; Choi, S. R.; Hou, C.; Plossl, K.; Kung, H. F. J. Nucl.Med. 2001, 42, 1556-1562.
  15. Lee, B. S.; Chu, S.; Lee, K. C.; Lee, B.-S.; Chi, D. Y.; Kim, S. E.;Choe, Y. S.; Song, Y. S.; Jin, C. Bioorg. Med. Chem. 2003, 11,4949-4958. https://doi.org/10.1016/j.bmc.2003.09.009
  16. Lee, B. S.; Chu, S.; Lee, B.-S.; Chi, D. Y.; Song, Y. S.; Jin, C.Bioorg. Med. Chem. Lett. 2002, 12, 811-815. https://doi.org/10.1016/S0960-894X(02)00028-8
  17. In, M. Y.; Chi, D. Y.; Choi, S. J.; Park, K. B.; Cho, C. G. Bull.Korean Chem. Soc. 2002, 23, 1439-1444. https://doi.org/10.5012/bkcs.2002.23.10.1439
  18. Lee, B. S.; Chu, S.; Lee, I. Y.; Lee, B.-S.; Song, C. E.; Chi, D. Y.Bull. Korean Chem. Soc. 2000, 21, 860-866.
  19. Lee, B. S.; Chu, S.; Lee, B. C.; Chi, D. Y.; Choe, Y. S.; Jeong, K.J.; Jin, C. Bioorg. Med. Chem. Lett. 2000, 10, 1559-1562. https://doi.org/10.1016/S0960-894X(00)00290-0
  20. Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214-220. https://doi.org/10.15227/orgsyn.063.0214
  21. Clark, R. D.; Repke, D. B. Heterocycles 1984, 22, 195-221. https://doi.org/10.3987/R-1984-01-0195
  22. Hama, Y.; Nobuhara, Y.; Aso, Y.; Otsubo, T.; Ogura, F. Bull.Chem. Soc. Jpn. 1988, 61, 1683-1686. https://doi.org/10.1246/bcsj.61.1683
  23. Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493-7496. https://doi.org/10.1016/S0040-4039(00)60162-4
  24. Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980-3984. https://doi.org/10.1021/jo01350a023
  25. Assignments of ¹H and $^13C$ NMR based on 2D-HETCOR:

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