Determination of the pK(a) values for polycationic species derived from 9-hydroxy and 9-aminothiazolo[5,4-b]quinolines. A problem related to the tautomerism of these systems

Tetrahedron

Volumn 52, Issue 36, 1996, Pages 11929-11946

  Alvarez Ibarra, Carlos ^a   Fernández Granda, Rocío ^a   Quiroga, Maria L ^a   Pingarron J M ^a   Pedrero, M ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE; THIAZOLE DERIVATIVE; THIAZOLO[5,4 B]QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PKA; PRIORITY JOURNAL;

EID: 0030565486     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00690-4     Document Type: Article

References (61)

1. 1. Wilson, W. D.; Jones, R. L. Intercalation Chemistry; Whittingham, M. S., Jackson, J. A., Eds., Academic Press, New York, 1981, Chapter 14.
2. 2. a) Albert, A., Drug Design; Ariens, E. J. Ed.; Academic Press, New York, 1970; Chap. 5.
3. b) Atwell, G. J., Cain, B. F., Denny, W. A. J. Med. Chem. 1977, 20, 1128.
4. c) Waring, M. J. Eur. J. Cancer 1976, 12, 995.
5. d) Feigon, J.; Denny; W. A., Leupin, W.; Kearns, D. R. J. Med. Chem. 1984, 27, 450.
6. e) Baguley, B. C.; Denny, W A.; Atwell, G. H.; Cain, B. F. J. Med. Chem. 1981, 24, 520.
7. 3 Alvarez-Ibarra, C.; Fernandez-Granda, R.; Quiroga, M. L.; Carbonell, A.; Cardenas, F.; Giralt, E. J. Med. Chem. (submitted).
8. 4. Ref. 1, pp. 446-447.
9. 5. Miller, K. J.; Newlin, D. D. Biopolymers 1982, 21, 633.
10. 6. Lerman, L. S. J. Mol. Biol. 1961, 3, 18.
11. 7. Waring, M. J. J. Mol. Biol. 1970, 54, 247.
12. 8. Lerman, L. S. Proc. Nat. Acad. Sci. U. S. A. 1965, 49, 94.
13. b) Pritcard, N. J.; Blake, A.; Peacocke, A. R. Nature 1966, 212, 1360.
14. c) Blake, A.; Peacocke, A. R. Biopolymers 1968, 6. 1225.
15. 9. Zuman, P. The Elucidation of Organic Electrode Processes, Academic Press, New York, 1969.
16. 10. Barker, G. C.; Jenkins, J. L. Analyst, 1952, 685.
17. 11. Barker, G. C., Jenkins, J. L. Anal. Chim. Acta 1958, 18, 118.
18. 12. Garbner, G. C. A. W. Z. Anal. Chem. 1960, 173, 79.
19. 13. Bond, A. M. Modern Polarographic Methods in Analytical Chemistry, Elsevier, London, 1980.
20. 14. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants. A Laboratory Manual; Chapman and Hall, London, 3rd Ed., 1984, pp. 70-101.
21. 15 Clark, T. A Handbook of Computational Chemistry. A Practical Guide to Chemical Structure and Energy Calculations, John Wiley, New York, 1985; pp 12-92.
22. 16. Program No. 318 Quantum Chemistry Program Exchange, Indiana University, Bloomington, Indiana, U. S. A.
23. 17. PCMODEL Molecular Modelling for Personal Computers and Workstations, Serena Software, Bloomington, Indiana , U S A.; 1992; version 4.0.
24. 18 Ref. 14, pp. 154-155.
25. 19. Pons, M.; Campayo, L.; Martinez-Balbas, M. A.; Azorin, P.; Navarro, P.; Giralt, E. J. Med. Chem 1991, 82, 34.
26. 20. Catalan, J.; Elguero, J.; Mo, O.; Paz, J. L. G. de; Perez, P.; Yañez, M. J. Org. Chem., 1984, 49, 4379.
27. 21 Katritzky, A. R. and Lagowski, J. M. Adv. Heterocyc. Chem. 1963, 1, 339.
28. 22 Beak, P. Acc. Chem. Res 1977, 10, 186.
29. 23 Johnson, C. D., Comprehensive Heterocyclic Chemistry, Boulton, A. J. and McKillop, A., Eds.; Pergamon Press, New York, 1984, Vol 2, pp. 99-164.
30. 24 Socrates, G., Infrared Characteristic Group Frquencies, John Wiley and Sons, New York, 1980, p. 73.
31. 25. a) Nyquist, R. A. Spectrochim. Acta 1963, 19, 509;
32. b) Nyquist, R. A. Spectrochim. Acta 1963, 19, 713;
33. c) Nyquist, R. A. Spectrochim. Acta 1963, 19, 1595;
34. d) Mclachlan, R. D. and Nyquist, R. A. Spectrochim. Acta 1964, 20, 1397.
35. 26. Zahn, H. and Kunde, J. Chem. Ber. 1961, 94, 2470.
36. 27 a) Cruz, A. de la; Ph. D. Thesis, Universidad Complutense, Madrid, 1992;
37. b) Cruz, A. de la; Elguero, J.; Goya, P.; Gotor, V.; Moros, F.; Clerq, E. de J. Chem. Res (S) 1992, 216,
38. (M) 1992, 1682.
39. 28. Katritzky, A. R.; Ellison, J.; Frank, J.; Rákóvzy, P.; Radics, L.; Gacs-Baitz, E Org. Magn. Resonan. 1981, 16, 280.
40. 29. Ref. 20, pp. 16-17.
41. 30. Witanowsky, M., Stefaniak, L. and Webb, G. A. Ann. Report NMR Spectroscopy, 1986, 18, 1.
42. 31. Phillipsborn, W. and Müller, R. Angew Chem., Int. Ed. Eng., 1986, 25, 383.
43. 2, and formamide as external reference.
44. 27
45. 34. Witanowsky, M., Stefaniak, L., Januszewski, and Webb, G. A. Tetrahedron 1971, 27, 3129.
46. 35. Saito, H., Tanaka, Y. and Nagata, S. J. Am. Chem. Soc., 1973, 95, 324.
47. 36 Stewart, J. J. P. J. Computer-Aided Design 1990, 4, 1.
48. 37 a) Baumer, L , Sala, G. and Sello, G. Tetrahedron Comp. Methodology 1989, 2, 37;
49. b) Baumer, L., Sala, G. and Sello Tetrahedron Comp. Methodology, 1989, 2, 93;
50. c) Baumer, L., Sala, G. and Sello, G. Tetrahedron Comp. Methodology 1989, 2, 105.
51. 38. a) Mulliken, R. S. J. Chem. Phys 1949, 46, 497;
52. b) Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833;
53. c) Reed, A. E., Weinstock, R. B. and Weinhold, F. J. Chem. Phys. 1985, 83, 735;
54. d) Bader. R. F. W. Acc. Chem. Res. 1985, 18, 9;
55. e) Bader, R. F. W. and Nguyen-Dang, T. T. Adv. Quantum Chem. 1981, 14, 63;
56. f) Bader, R. F. W., Nguyen-Dang, T. T. and Tal, Y. Rep. Progr. Phys. 1981, 44, 893;
57. g) Bader, R. F. W. J. Chem. Phys. 1984, 80, 1943;
58. h) Christoffersen, R. E. and Baker, K. A. Chem. Phys. Lett. 1971, 8, 4;
59. i) Boydand, R. J. and Edgecombe, J. Am. Chem. Soc, 1988, 110, 4182;
60. j) Edgecombe, K. E. and Boyd, R. J. J. Chem. Soc. Faraday Trans. 2 1987, 83, 1307;
61. k) Hehre, W. J., Radom, L., Schleyer, P. von R. and Pople, J. A.; Ab initio Molecular Orbital Theory; John Wiley and Sons, New York, 1986.