Bulletin of the Korean Chemical Society

  • 제32권7호
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  • Pages.2453-2456
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  • 2011
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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An Efficient Solid-Phase Synthesis of α-1,2,3-Triazoloamide Derivatives via Click Chemistry

  • Gong, Young-Dae (Department of Chemistry, Dongguk University) ;
  • Min, Kyung-Hoon (College of Pharmacy, Chung-Ang University) ;
  • Lee, Tae-Ho (Research Institute of Pharmaceutical Sciences, College of Pharmacy, Kyungpook National University)
  • 투고 : 2011.04.26
  • 심사 : 2011.05.09
  • 발행 : 2011.07.20
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참고문헌

  1. Dolle, R. E.; Le Bourdonnec, B.; Worm, K.; Morales, G. A.; Thomas, C. J.; Zhang, W. J. Comb. Chem. 2010, 12, 765-806. https://doi.org/10.1021/cc100128w
  2. Gong, Y.-D.; Lee, T. J. Comb. Chem. 2010, 12, 393-409. https://doi.org/10.1021/cc100049u
  3. Dolle, R. E.; Le Bourdonnec, B.; Goodman, A. J.; Morales, G. A.; Thomas, C. J.; Zhang, W. J. Comb. Chem. 2009, 11, 739-790. https://doi.org/10.1021/cc9000828
  4. Dolle, R. E.; Le Bourdonnec, B.; Goodman, A. J.; Morales, G. A.; Thomas, C. J.; Zhang, W. J. Comb. Chem. 2008, 10, 753-800. https://doi.org/10.1021/cc800119z
  5. Kennedy, J. P.; Williams, L.; Bridges, T. M.; Daniels, R. N.; Weaver, D.; Lindsley, C. W. J. Comb. Chem. 2008, 10, 345-354. https://doi.org/10.1021/cc700187t
  6. Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; In Combinatorial Chemistry: Drugs, Catalysts, Materials; Wiley-VCH: Weinheim, Germany, 2002.
  7. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; p 1-176.
  8. Smithe, C. D.; Baxendale, I. R.; Lanners, S.; Hayward, J. J.; Smith, S. C.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 1559.-1561. https://doi.org/10.1039/b702995k
  9. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004-2021. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
  10. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68.
  11. Manetsch, R.; Krasinski, A.; Radic, Z.; Raushel, J.; Taylor, P.; Sharpless, K. B.; Kolb, H. C. J. Am. Chem. Soc. 2004, 126, 12809-12818 https://doi.org/10.1021/ja046382g
  12. Lee, L. V.; Mitchell, M. L.; Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. J. Am. Chem. Soc. 2003, 125, 9588-9589. https://doi.org/10.1021/ja0302836
  13. Kolb, H. C.; Sharpless, K. B. Drug Discov. Today2003, 8, 1128-1137. https://doi.org/10.1016/S1359-6446(03)02933-7
  14. Lewis, W. G.; Green, L. G.; Grynszpan, F.;Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B.Angew. Chem. Int. Ed. 2002, 41, 1053-1055. https://doi.org/10.1002/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO;2-4
  15. Kim, S.; Cho, M.; Lee, T.; Lee, S.; Min, H.-Y.; Lee, S. K. Bioorg. Med. Chem. Lett. 2007, 17, 4584-4587. https://doi.org/10.1016/j.bmcl.2007.05.086
  16. Lee, T.; Cho, M.; Ko, S.-Y.; Youn, H.-J.; Baek, D. J.; Cho, W.-J.; Kang, C.-Y.;Kim, S. J. Med. Chem. 2007, 50, 585-589. https://doi.org/10.1021/jm061243q
  17. Wang, Q.; Chittaboina, S.; Barnhill, H. N. Lett. Org. Chem. 2005, 2, 293-301. https://doi.org/10.2174/1570178054038885
  18. Vang, T.; Xie, Y.; Liu, W. H.; Vidovi, D.; Liu, Y.; Wu, S.; Smith, D. H.; Rinderspacher, A.; Chung, C.; Gong, G.; Mustelin, T.; Landry, D. W.; Rickert, R. C.; Schürer, S. C.; Deng, S.-X.; Tautz, L. J. Med. Chem. 2011, 54, 562-571. https://doi.org/10.1021/jm101004d
  19. Ngai, M. H.; Yang, P.-Y.; Liu, K.; Shen, Y.; Wenk, M. R.; Yao, S. Q.; Lear, M. J. Chem. Commun. 2010, 46, 8335-8337. https://doi.org/10.1039/c0cc01276a
  20. Zou, Y.; Albohy, A.; Sandbhor, M.; Cairo, C. W. Bioorg. Med. Chem. Lett. 2010, 20, 7529-7533. https://doi.org/10.1016/j.bmcl.2010.09.111
  21. Reed, C. S.; Huigens, R. W., III.; Rogers, S. A.; Melander, C.Bioorg. Med. Chem. Lett. 2010, 20, 6310-6312. https://doi.org/10.1016/j.bmcl.2010.08.075
  22. Xie, J.; Seto, C. T. Bioorg. Med. Chem. 2007, 15, 458-473. https://doi.org/10.1016/j.bmc.2006.09.036
  23. Kumar, D.; Reddy, V. B.; Kumar, A.; Mandal, D.; Tiwari, R.; Parnag, K.Bioorg. Med. Chem. Lett. 2011, 21, 449-452. https://doi.org/10.1016/j.bmcl.2010.10.121
  24. Vantikommu, J.; Palle, S.; Reddy, P. S.; Ramanatham, V.; Khagga, M.; Rallapothula, V. R. Eur. J. Med. Chem. 2010, 45, 5044-5050. https://doi.org/10.1016/j.ejmech.2010.08.012
  25. Fivush, A. M.; Wilson, T. M. Tetrahedron Lett. 1997, 38, 7151-7154. https://doi.org/10.1016/S0040-4039(97)01771-1
  26. Duval, R.; Kolb, S.; Braud, E.; Genest, D.; Garbay, C. J. Comb. Chem. 2009, 11, 947-950. https://doi.org/10.1021/cc900140f
  27. Bonnet, D.; Riche, S.; Loison, S.; Dagher, R.; Frantz, M.-C.; Boudier, L.; Rahmeh, R.; Mouillac, B.; Haiech, J.; Hibert, M. Chem. Eur. J. 2008, 14, 6247-6254. https://doi.org/10.1002/chem.200800273
  28. Donnelly, P. S.; Zanatta, S. D.; Zammit, S. C.; White, J. M.; Williams, S. J. Chem. Commun. 2008, 2459-2461.
  29. Lv, G.; Mai, W.; Jin, R.; Gao, L. Synlett 2008, 1418-1422.
  30. Cao, J.; Huang, X. J. Comb. Chem. 2008, 10, 526-533. https://doi.org/10.1021/cc800034v
  31. Ananthanarayanan, C.; Ramakrishnan, V. T. Indian J. Chem. B 1989, 28B, 228-230.

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