Bulletin of the Korean Chemical Society

  • 제30권8호
  • /
  • Pages.1743-1748
  • /
  • 2009
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

2-Aminothiazolinium Based Tripodal Receptors:Synthesis and Recognition of Oxoanions

  • Nguyen, Quynh Pham Bao (Department of Applied Chemistry and Center for Functional Nano Fine Chemicals, Chonnam National University) ;
  • Le, Thanh Nguyen (Department of Applied Chemistry and Center for Functional Nano Fine Chemicals, Chonnam National University) ;
  • Kim, Taek-Hyeon (Department of Applied Chemistry and Center for Functional Nano Fine Chemicals, Chonnam National University)
  • 발행 : 2009.08.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Novel 2-aminothiazolinium based tripodal receptors were designed and synthesized. The binding property of these receptors toward various anions was investigated by the isothermal titration calorimetry (ITC) method. Receptor 4 recognized the acetate anion with 1:1 stoichiometry, whereas it bound the other oxoanions such as sulfate and phosphate in complex modes. By modifying the phenyl groups at the 4-position of the thiazoline rings of the tripodal receptor 4 to induce a mutual aromatic stacking interaction among the three ligands, receptor 10 showed totally different binding behavior, which gave rise to the 1:1 binding mode for the sulfate anion. This result was confirmed by ESI MS spectrometry.

키워드

참고문헌

  1. Southan, G. J.; Zingarelli, B.; O'Connor, M.; Salzman, A. L.; Szabo, C. Br. J. Pharmacol. 1996, 117, 619-632
  2. Moore, W. M.; Webber, R. K.; Fok, K. F.; Jerome, G. M.; Connor, J. R.; Manning, P. T.; Wyatt, P. S.; Misko, T. P.; Tjoeng, F. S.; Currie, M. G. J. Med. Chem. 1996, 39, 669-672 https://doi.org/10.1021/jm950766n
  3. Hirashima, A.; Yoshii, Y.; Eto, M. Agric. Biol. Chem. 1991, 55, 2537-2545 https://doi.org/10.1271/bbb1961.55.2537
  4. Hirashima, A.; Yoshii, Y.; Eto, M. Biosci. Biotech. Biochem. 1992, 56, 1062-1065 https://doi.org/10.1271/bbb.56.1062
  5. Hirashima, A.; Tomita, J.; Pan, C.; Taniguchi, E.; Eto, M. Bioorg. & Med. Chem. 1997, 5, 2121-2128 https://doi.org/10.1016/S0968-0896(97)00136-3
  6. Caujolle, R.; Amarouch, H.; Payard, M.; Loiseau, P. R.; Bories, C.; Loiseau, P. M.; Garyral, P. Eur. J. Med. Chem. 1989, 24, 287-292 https://doi.org/10.1016/0223-5234(89)90011-1
  7. Bender, P. E.; Hill, D. T.; Often, P. H.; Razgaitis, K.; Lavanchy, P.; Stringer, O. D.; Sutton, B. M.; Griswold, D. E.; DiMartino, M.; Walz, D. T.; Lantos, I.; Ladd, C. B. J. Med. Chem. 1985, 28, 1169-1177 https://doi.org/10.1021/jm00147a008
  8. Tobey, S. L.; Jones, B. D.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 4026-4027 https://doi.org/10.1021/ja021390n
  9. Xie, H.; Yi, S.; Yang, X.; Wu, S. New J. Chem. 1999, 23, 1105-1110 https://doi.org/10.1039/a905043d
  10. Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534 https://doi.org/10.1021/ja980990c
  11. Cabell, L. A.; Monahan, M. K.; Anslyn, E. V. Tetrahedron Letters 1999, 40, 7753-7756 https://doi.org/10.1016/S0040-4039(99)01651-2
  12. Katayev, E. A.; Ustynyuk, Y. A.; Sessler, J. L. Coordination Chemistry Reviews 2006, 250, 3004-3037 https://doi.org/10.1016/j.ccr.2006.04.013
  13. Kubo, Y.; Ishihara, S.; Tsukahara, M.; Tokita, S. J. Chem. Soc., Perkin Trans. 2 2002, 1455-1460
  14. Kubo, Y.; Kato, M.; Misawa, Y.; Tokita, S. Tetrahedron Letters 2004, 45, 3769-3773 https://doi.org/10.1016/j.tetlet.2004.03.076
  15. Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654
  16. Nishizawa, S.; Cui, Y. Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 2002, 866-870
  17. Yeo, W. S.; Hong, J. I. Tetrahedron Letters 1998, 39, 3769-3772 https://doi.org/10.1016/S0040-4039(98)00612-1
  18. Yeo, W. S.; Hong, J. I. Tetrahedron Letters 1998, 39, 8137-8140 https://doi.org/10.1016/S0040-4039(98)01806-1
  19. Song, H. R.; Kim, D. S.; Kim, S. G.; Choi, H. J.; Ahn, K. H. Tetrahedron Letters 2004, 45, 723-727 https://doi.org/10.1016/j.tetlet.2003.11.048
  20. Blondeau, P.; Segura, M.; Perez-Fernandez, R.; Mendoza, J. D. Chem. Soc. Rev. 2007, 36, 198-210 https://doi.org/10.1039/b603089k
  21. Berger, M.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 2694-2696 https://doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2694::AID-ANIE2694>3.0.CO;2-Q
  22. Han, F. S.; Osajima, I. H.; Cheung, M.; Tokuyama, H.; Fukuyama, T. Chem. Euro. J. 2007, 13, 3026-3038 https://doi.org/10.1002/chem.200601446
  23. Wallace, K. J.; Hanes, R.; Anslyn, E.; Morey, J.; Kilway, K. V.; Siegel, J. Synthesis 2005, 12, 2080-2083
  24. Kim, T. H.; Cha, M.-H. Tetrahedron Letters 1999, 40, 3125-3128 https://doi.org/10.1016/S0040-4039(99)00457-8
  25. Turner, D. R.; Paterson, M. J.; Steed, J. W. J. Org. Chem. 2006, 71, 1598-1608 https://doi.org/10.1021/jo052339f
  26. Piatek, P. Tetrahedron Letters 2007, 48, 4427-4430 https://doi.org/10.1016/j.tetlet.2007.04.073
  27. Belcher, W. J.; Fabre, M.; Farhan, T.; Steed, J. W. Org. Biomol. Chem. 2006, 4, 781-786 https://doi.org/10.1039/b516027h
  28. Qiao, Y. H.; Lin, H.; Shao, J.; Lin, H. K. Chinese Journal of Chemistry 2008, 26, 611-614 https://doi.org/10.1002/cjoc.200890115
  29. Kim, J.; Raman, B.; Ahn, K. H. J. Org. Chem. 2006, 71, 38-45 https://doi.org/10.1021/jo051630s
  30. Hunter, C. A.; Lawson, K. R.; Perkin, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669
  31. Waters, M. L. Current Opinion in Chemical Biology 2002, 6, 736-741 https://doi.org/10.1016/S1367-5931(02)00359-9

피인용 문헌

  1. Survey of the year 2009: applications of isothermal titration calorimetry vol.24, pp.1, 2011, https://doi.org/10.1002/jmr.1073
  2. Artificial Receptors for the Recognition of Phosphorylated Molecules vol.111, pp.11, 2011, https://doi.org/10.1021/cr100242s
  3. Recognition and separation of sulfate anions vol.41, pp.8, 2012, https://doi.org/10.1039/c2cs15293b
  4. Silver(I) Polymer of Tripodal Amine: Synthesis, Structure and Photoluminescence vol.26, pp.5, 2016, https://doi.org/10.1007/s10904-016-0406-7
  5. Hybrid cyclic peptide–thiourea cryptands for anion recognition vol.47, pp.1, 2009, https://doi.org/10.1039/c0cc02223c