Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor

Tetrahedron

Volumn 66, Issue 44, 2010, Pages 8544-8550

  Silva, Ana M G ^a   Leite, Andreia ^a   Andrade, Mariana ^a   Gameiro, Paula ^a   Brandão, Paula ^c   Felix, Vítor ^c   De Castro, Baltazar ^a   Rangel, Maria ^b  

^a UNIVERSITY OF PORTO   (Portugal)

^b Faculdade de Farmácia da Universidade do Porto   (Portugal)

^c UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

3 Hydroxy 4 pyridinones; Dihydroxypyridinium forms; Fluorescent sensors; Naphthalene dyes

Indexed keywords

NAPHTHALENE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; FLUORESCENCE; HEATING; MICROWAVE IRRADIATION; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION TIME; SENSOR; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 77957749950     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.08.065     Document Type: Article

References (47)

1. J.R. Lakowicz Principles of Fluorescence Spectroscopy 3 ed. 2006 Springer Berlin, Heidelberg
2. A.P. de Silva, H.Q. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, and T.E. Rice Chem. Rev. 97 1997 1515
3. V. Amendola, L. Fabbrizzi, M. Licchelli, C. Mangano, P. Pallavicini, L. Parodi, and A. Poggi Coord. Chem. Rev. 190-192 1999 649
4. V. Ljosa, and A.C. Carpenter Trends Biotechnol. 26 2008 527
5. M. Leopoldo, E. Lacivita, F. Berardi, and R. Perrone Drug Discovery Today 14 2009 706
6. Examples of fluorescence detection of metal ions:
7. D.W. Domaille, E.L. Que, and C.J. Chang Nat. Chem. Biol. 4 2008 168
8. J.L. Vinkenborg, M.S. Koay, and M. Merkx Curr. Opin. Chem. Biol. 14 2010 231
9. J. Burgess, and M. Rangel R.V. Eldik, Hydroxypyranones, Hydroxypyridinones, and their Complexes in Advances in Inorganic Chemistry Vol. 60 2008 Academic: University of Erlangen-Nurnberg Germany 167 Chapter 5
10. Z.D. Liu, and R.C. Hider Med. Res. Rev. 22 2002 26
11. T. Zhou, H. Neubert, D.Y. Liu, Y.M. Ma, X.L. Kong, W. Luo, S. Mark, and R.C. Hider J. Med. Chem. 49 2006 4171
12. T. Zhou, X.L. Kong, Z.D. Liu, D.Y. Liu, and R.C. Hider Biomacromolecules 9 2008 1372
13. G. Crisponi, and M. Remelli Coord. Chem. Rev. 252 2008 1225
14. M.A. Santos Coord. Chem. Rev. 252 2008 1213
15. H. Sakurai, A. Katoh, and Y. Yoshikawa Bull. Chem. Soc. Jpn. 79 2006 1645
16. Examples of (3,4-HPO)s fluorescent probes:
17. Y. Ma, W. Luo, P.J. Quinn, Z. Liu, and R.C. Hider J. Med. Chem. 47 2004 6349
18. S. Fakih, M. Podinovskaia, X. Kong, H.L. Collins, U.E. Schaible, and R.C. Hider J. Med. Chem. 51 2008 4539
19. A. Katoh, K. Ogino, and R. Saito Heterocycles 65 2005 2195
20. Examples of naphthalene-based fluorescent sensors:
21. R. Senthilnithy, M.D.P. De Costa, and H.D. Gunawardhana Luminescence 24 2008 203
22. H. Yang, Z.-Q. Liu, Z.-G. Zhou, E.-X. Shi, F.-Y. Li, Y.-K. Du, T. Yia, and C.-H. Huang Tetrahedron Lett. 47 2006 2911
23. N.K. Al-Rasbi, C. Sabatini, F. Barigelletti, and M.D. Ward Dalton Trans. 2006 4769
24. G.E. Tumambac, C.M. Rosencrance, and C. Wolf Tetrahedron 60 2004 11293
25. M.D.P. De Costa, and W.A.P.A. Jayasinghe J. Photochem. Photobiol., A 2004 162
26. F. Otón, A. Tárraga, M.D. Velasco, A. Espinosa, and P. Molina Chem. Commun. 2004 1658
27. Y. Kubo, M. Tsukahara, S. Ishihara, and S. Tokita Chem. Commun. 2000 653
28. M.S.T. Gonalves Chem. Rev. 109 2009 190 and references therein
29. K.-H. Lee, and B.-R. Huang Eur. J. Med. Chem. 37 2002 333
30. G. Petrillo, C. Fenoglio, E. Ognio, C. Aiello, D. Spinelli, M.A. Mariggi, M. Maccagno, S. Morganti, C. Cordazzo, and M. Viale Invest. New Drugs 25 2007 535
31. D.A. Patrick, S.A. Bakunov, S.M. Bakunova, E.V.K. Suresh Kumar, H. Chen, S.K. Jones, T. Wenzler, T. Barzcz, K.A. Werbovetz, R. Brun, and R.R. Tidwell Eur. J. Med. Chem. 44 2009 3543
32. Examples of microwave-assisted synthesis of organic dyes:
33. J.-J. Lee, A.G. White, J.M. Baumes, and B.D. Smith Chem. Commun. 46 2010 1068
34. D.Z. Mijin, M. Baghbanzadeh, C. Reidlinger, and C.O. Kappe Dyes Pigm. 85 2010 73
35. F. Nourmohammadian, and M.D. Gholami Synth. Commun. 40 2010 901
36. M.K. Abdel-Hamid, J.B. Bremner, J. Coates, P.A. Keller, C. Miländer, Y.S. Torkamani, B.W. Skelton, A.H. White, and A.C. Willis Tetrahedron Lett. 50 2009 6947
37. P. Thirumurugan, D. Muralidharan, and P.T. Perumal Dyes Pigm. 81 2009 245
38. T.N. Glasnov, and C.O. Kappe QSAR Comb. Sci. 26 2007 1261
39. J. March Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 4th ed. 1992 John Wiley New York, NY, United States of America 70
40. P. Beak, F.S. Fry Jr., J. Lee, and F. Steele J. Am. Chem. Soc. 98 1976 171
41. H.B. Schlegel, P. Gund, and E.M. Fluder J. Am. Chem. Soc. 104 1982 5347
42. A. El-Jammal, P.L. Howell, M.A. Turner, N. Li, and D.M. Templeton J. Med. Chem. 37 1994 461
43. 6.
44. M.A. Santos, M. Gil, S. Marques, L. Gano, G. Cantinho, and S. Chaves J. Inorg. Biochem. 92 2002 43
45. G.M. Sheldrick SHELXL-97, Computer Program for Crystal Structure Refinement 1997 University of Göttingen Germany
46. G.M. Sheldrick Acta Crystallogr., Sect. A 46 1990 467
47. L. Spek 'PLATON', in A Multipurpose Crystallographic Tool 2008 Utrecht University Utrecht, The Netherlands