Synthesis of a novel cyclic donor-acceptor conjugate for selective recognition of ATP

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5765-5768

  Neelakandan, Prakash P ^a   Hariharan, Mahesh ^a   Ramaiah, Danaboyina ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE NUCLEOTIDE; ADENOSINE TRIPHOSPHATE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ADENINE NUCLEOTIDES; ADENOSINE TRIPHOSPHATE; ELECTROSTATICS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 30044452754     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052246k     Document Type: Article

References (33)

1. (a) Simon, M. I.; Strathmann, M. P.; Gautam, N. Science 1991, 252, 802.
2. (b) Moro, S.; Deflorian, F.; Spalluto, G.; Pastorin, G.; Cacciari, B.; Kim, S.-K.; Jacobson, K. A. Chem. Commun. 2003, 2949.
3. (a) Hosseini, M. W.; Blacker, A. J.; Lehn, J.-M. J. Am. Chem. Soc. 1990, 112, 3896.
4. (b) Marquez, C.; Pischel, U.; Nau, W. M. Org. Lett. 2003, 5, 3911.
5. (a) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245.
6. (b) Tumir, L. M.; Piantanida, I.; Novak, P.; Zinic, M. J. Phys. Org. Chem. 2002, 15, 599.
7. (c) Piantanida, I.; Tomisic, V.; Zinic, M. J. Chem. Soc., Perkin Trans. 2 2000, 375.
8. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
9. Sessler, J. L.; Kral, V.; Shishkanova, T. V.; Gale, P. A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4848.
10. Inouye, M.; Kim, K.; Kitao, T. J. Am. Chem. Soc. 1992, 114, 778.
11. (a) Vickers, M. S.; Martindale, K. S.; Beer, P. D. J. Mater. Chem. 2005, 15, 2784.
12. (b) Reynes, O.; Bucher, C.; Moutet, J.-C.; Royal, G.; Aman, E. S. Chem. Commun. 2004, 428.
13. (c) Butterfield, S. M.; Waters, M. L. J. Am. Chem. Soc. 2003, 125, 9580.
14. (d) Albelda, M. T.; Aguilar, J.; Alves, S.; Aucejo, R.; Diaz, P.; Lodeiro, C.; Lima, J. C.; Espana, G. E.; Pina, F.; Soriano, C. Helv. Chim. Acta 2003, 86, 3118.
15. Lipscomb, W. N.; Strater, N. Chem. Rev. 1996, 96, 2375.
16. Lee, D. H.; Kim, S. Y.; Hong, J.-I. Angew. Chem., Int. Ed. 2004, 43, 4777.
17. The minimum energy conformer of 1 was obtained by AM1 calculations using PC TITAN software from Wave function Inc.; 18401 von Karman, Suite 370, Irvine, CA 92612.
18. +.
19. +.
20. (a) Flood, A. H.; Liu, Y.; Stoddart, J. F. Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004; p 485.
21. (b) Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H.-R.; Jeppesen, J. O.; Huang, T. J.; Brough, B.; Baller, M.; Magonov, S.; Solares, S. D.; Goddard, W. A.; Ho, C.-M.; Stoddart, J. F. J. Am. Chem. Soc. 2005, 127, 9745.
22. (c) Badjic, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723.
23. (d) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348.
24. (a) Benesi, H.; Hildebrand, J. J. Am. Chem. Soc. 1949, 71, 2703.
25. (b) Arun, K. T.; Ramaiah, D. J. Phys. Chem. A 2005, 109, 5571.
26. (a) Joseph, J.; Eldho, N. V.; Ramaiah, D. J. Phys. Chem. B 2003, 107, 4444.
27. (b) Joseph, J.; Eldho, N. V.; Ramaiah, D. Chem. Eur. J. 2003, 9, 5926.
28. Boulas, P. L.; Kaifer, M. G.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216.
29. Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417.
30. Hunter, C. A.; Lawson, K. R.;Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651.
31. Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442.
32. Carmona, C.; Balon, M.; Coronilla, A. S.; Munoz, M. A. J. Phys. Chem. A 2004, 108, 1910.
33. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210.