Structure and molecular interactions of anti-thyroid drugs. Part 3. Methimazole: A diiodine sponge

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 1998, Pages 1545-1551

  Laurence, Christian ^a   El Ghomari, Mohamed J ^b   Le Questel, Jean Yves ^a   Berthelot, Michel ^a   Mokhlisse, Rachid ^b  

^a UNIVERSITÉ DE NANTES   (France)

^b FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002914467     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803002b     Document Type: Article

References (70)

1. Part 2. C. Laurence, M. J. El Ghomari and M. Berthelot, J. Chem. Soc., Perkin Trans. 2, 1998, 1163.
2. J. Buxeraud, in Traité de chimie thérapeutique, Tec et Doc Lavoisier, Paris, 1995, vol. 4, ch. 18.
3. J. Leclere, J. Orgiazzi, B. Rousser, J. L. Schlienger and J. L. Wemeau, La thyroïde, Exapnsion scientifique française, Paris, 1992.
4. (a) R. P. Lang, J. Am. Chem. Soc., 1962, 84, 1185;
5. (b) A. F. Grand and M. Tamres, J. Phys. Chem., 1970, 74, 208.
6. K. R. Bhaskar, R. K. Gosavi and C. N. R. Rao, Trans. Faraday Soc., 1966, 62, 29.
7. R. P. Lang, J. Phys. Chem., 1968, 72, 2129.
8. J. Buxeraud, A. C. Absil, J. Claude, C. Raby, G. Catanzano and C. Beck, Eur. J. Med. Chem., 1985, 20, 43.
9. C. Raby, J. F. Lagorce, A. C. Jambut-Absil, J. Buxeraud and G. Catanzano, Endocrinology, 1990, 126, 1683.
10. C. Raby, J. Claude, C. Moesch and J. Buxeraud, C. R. Hebd. Seances Acad. Sci., Ser. C, 1979, 288, 319.
11. A. Suszka, J. Chem. Soc., Perkin Trans. 2, 1985, 531.
12. N. J. Rose and R. S. Drago, J. Am. Chem. Soc., 1959, 81, 6138.
13. R. S. Mulliken and W. B. Person, Molecular complexes, Wiley, New York, 1969.
14. (a) C. Laurence, M. Berthelot, J. Y. Le Questel and M. J. El Ghomari J. Chem. Soc., Perkin Trans. 2, 1995, 2075;
15. (b) G. G. Hammes and A. C. Park, J. Am. Chem. Soc., 1969, 91, 956.
16. G. Kjellin and J. Sandström, Acta Chem. Scand, 1969, 23, 2888.
17. R. Fauré, E. J. Vincent, G. Assef, J. Kister and J. Metzger, Org. Magn. Reson., 1977, 9, 688.
18. E. Bojarska-Olejnik, L. Stefaniak, M. Witanowski, B. T. Hamdi and G. A. Webb, Magn. Reson. Chem., 1985, 23, 166.
19. R. S. Balestreco, D. M. Forkey and J. G. Russell, Magn. Reson. Chem., 1986, 24, 651.
20. M. J. El Ghomari, Ph.D. Thesis, Nantes, 1996.
21. -1.
22. M. J. El Ghomari, R. Mokhlisse, C. Laurence, J. Y. Le Questel and M. Berthelot, J. Phys. Org. Chem., 1997, 10, 669.
23. C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165.
24. M. T. Molina, W. Bouab, M. Esseffar, M. Herreros, R. Notario, J. L. M. Abboud, O. Mo and M. Yáñez, J. Org. Chem., 1996, 61, 5485.
25. P. J. Taylor and A. R. Wait, J. Chem. Soc., Perkin Trans. 2, 1986, 1765.
26. A. Rogstad and E. Augdahl, Acta Chem. Scand., 1971, 25, 225.
27. G. Guihéneuf, J. L. M. Abboud and W. Bouab, Can. J. Chem., 1987, 65, 2106.
28. F. Freeman, J. W. Ziller, H. N. Po and M. C. Keindl, J. Am. Chem. Soc., 1988, 110, 2586.
29. F. Cristiani, F. Demartin, F. A. Devillanova, F. Isaia, G. Saba and G. Verani, J. Chem. Soc., Dalton Trans., 1992, 3553.
30. F. Cristiani, F. A. Devillanova, A. Garau, F. Isaia, V. Lippolis and G. Verani, Heteroat. Chem., 1994, 5, 65.
31. R. Sugisaki, T. Tanaka and E. Hirota, J. Mol. Spectrosc., 1974, 49, 241.
32. F. H. Herbstein and W. Schwotzer, J. Am. Chem. Soc., 1984, 106, 2367.
33. e cycle, Marrakech, 1984.
34. F. A. Devillanova and G. Verani, Tetrahedron, 1979, 35, 511.
35. C. Guimon, G. Pfister-Guillouzo, M. Arbelot and M. Chanon, Tetrahedron, 1974, 3831.
36. F. Cristiani, F. A. Devillanova, A. Diaz, F. Isaia and G. Verani, Heteroat. Chem., 1990, 1, 363.
37. F. A. Devillanova and G. Verani, J. Heterocycl. Chem., 1979, 16, 945.
38. F. Cristiani, F. A. Devillanova, A. Diaz and G. Verani, J. Chem. Soc., Perkin Trans. 2, 1984, 1383.
39. R. Foster, Organic charge-transfer complexes, Academic Press, London, 1969.
40. (a) R. West, D. L. Powell, L. S. Whatley, M. K. T. Lee and P. von R. Schleyer, J. Am. Chem. Soc., 1962, 84, 3221;
41. (b) D. A. K. Jones and J. G. Watkinson, J. Chem. Soc., 1964, 2366.
42. F. Cristiani, F. A. Devillanova, F. Isaia, V. Lippolis and s. Verani, Polyhedron, 1995, 14, 2937.
43. H. A. Bent, Chem. Rev., 1968, 68, 587.
44. N. Ramasubbu, R. Partharsarathy and P. Murray-Rust, J. Am. Chem. Soc., 1986, 108, 4308.
45. T. Brink, J. S. Murray and P. Politzer, Int. J. Quantum Chem., 1992, 19, 57.
46. E. Gentric, J. Lauransan, C. Roussel and J. Metzger, J. Chem. Soc., Perkin Trans. 2, 1977, 1015.
47. E. A. Allen and L. W. Reeves, J. Phys. Chem., 1962, 66, 613.
48. T. Nakashima and A. Taurog, Clin. Endocrinol., 1979, 10, 637.
49. A. Melander, B. Hallengren, S. Rosendal-Helgesen, A. K. Sjöberg and E. Wahlin-Boll, Eur. J. Clin. Pharmacol., 1980, 17, 295.
50. R. Jansson, P. A. Dalhlberg and B. Lindström, Int. J. Clin. Pharmacol., Ther. Toxicol., 1983, 21, 505.
51. (a) A. Taurog, Endocrinology, 1976, 98, 1031;
52. (b) T. Nakashima, A. Taurog and G. Riesco, Endocrinology, 1978, 103, 2187;
53. (c) H. Engler, A. Taurog and M. L. Dorris, Endocrinology, 1982, 110, 190;
54. (d) H. Engler, A. Taurog, C. Luthy and M. L. Dorris, Endocrinology, 1983, 112, 86;
55. (e) A. Shiroozu, A. Taurog, H. Engler and M. L. Dorris, Endocrinology, 1983, 113, 362;
56. (f) A. Taurog, M. L. Dorris and F. S. Guziec, Endocrinology, 1989, 124, 30.
57. J. Pelmont, Enzymes catalyseurs du monde vivant, Presses universitaires, Grenoble. 1995.
58. R. W. Hay, Bio-inorganic Chemistry, Wiley, New York, 1984.
59. A. M. English, Encyclopedia of inorganic chemistry, ed. R. B. King, Wiley, New York, 1994, vol. 4, p. 1682.
60. M. Berthelot, F. Besseau and C. Laurence, Eur. J. Org. Chem., 1998, 925.
61. J. L. M. Abboud, R. Notario, L. Santos and C. Lopez-Mardomingo, J. Am. Chem. Soc., 1989, 111, 8960.
62. J. Pommier, L. Sokoloff and J. Nunez, Eur. J. Biochem., 1973, 38, 497.
63. R. P. Magnusson and A. Taurog, Biochem. Biophys. Res. Commun., 1983, 112, 475.
64. (a) H. L. Holland, Organic syntheses with oxidative enzymes, VCH, New York, 1991;
65. (b) S. L. Neidelman and J. Geigert, Biohalogenation, Ellis Horwood, Chichester, 1986.
66. B. Davidson, M. Soodak, J. T. Neary, H. V. Strout, J. D. Kieffer, H. Mover and F. Maloof, Endocrinology, 1978, 103, 871.
67. G. Hung-Yin Lin and H. Hope, Acta Crystallogr., Sect. B, 1972, 28, 643.
68. O. Foss, J. Johnsen and O. Tvedten, Acta Chem. Scand., 1958, 12, 1782.
69. F. Bigoli, M. A. Pellinghelli, G. Crisponi, P. Deplano and E. F. Trogu, J. Chem. Soc., Dalton Trans., 1985, 1349.
70. H. N. Po, Z. Shariff, J. A. Masse, F. Freeman and M. C. Keindl-Yu, Phosphorus, Sulfur Silicon Relat. Elem., 1991, 63, 1.