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Heteroaromatic thioamides: Structure and stability of charge transfer complexes with iodine, antithyroid activity

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Abstract

The review generalizes the structural studies on the products of the interaction of antithyroid preparations (heteroaromatic thioamides) with iodine. The n-σ* adducts of imidazol, thiazol, oxazole, pyridine, uracil derivatives with molecular iodine, iodinium salts, and also disulfides formed as a result of thione oxidation in iodine-coordinating solvents are considered. Based on mainly single crystal X-ray diffraction and Raman spectroscopy data, the structural parameters of iodine molecular complexes are shown to be highly sensitive to changes in the type of a heteroatom and substituents in the heteroring. The effect of the structure of heteroaromatic thioamides on their antithyroid activity is analyzed.

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References

  1. M. Vieites, P. Smircich, B. Parajòn-Costa, et al., J. Biol. Inorg. Chem., 13, No. 5, 723 (2008).

    Article  CAS  Google Scholar 

  2. J. Franklyn, Clin. Med., 3, 11 (2003).

    Google Scholar 

  3. S. Sahasranaman, D. Howard, and S. Roy, Eur. J. Clin. Pharmacol., 64, No. 8, 753 (2008).

    Article  CAS  Google Scholar 

  4. Pat. 5945426 US, Ross. Khim. Zh., 19O102 (2000).

  5. A. H. Abdel-Rahman and M. T. Abdel-Aal, Pharmazie, 53, 377 (1998).

    CAS  Google Scholar 

  6. Pat. 98112915 Europe, Ross. Khim. Zh., 23O136 (1999).

  7. J. S. Larson, A. M. T. Abdel, E. B. Pedersen, et al., J. Heterocycl. Chem., 38, 679 (2001).

    Article  Google Scholar 

  8. E. A. Sudbeck, C. Mao, T. K. Venkatachalam, et al., Antimicrob. Agents Chemother., 42, No. 12, 3225 (1998).

    CAS  Google Scholar 

  9. C. Laurence, M. J. El Ghomari, and M. Berthelot, J. Chem. Soc., Perkin Trans 2, 1163 (1998).

    Google Scholar 

  10. C. Laurence, M. J. El Ghomari, and Lucon M., J. Chem. Soc., Perkin Trans 2, 1159 (1998).

    Google Scholar 

  11. W. M. Kettyle and R. A. Arky, Endocrine Pathophysiology, Lippincott-Raven, Philadelphia (1998).

  12. A. I. Kubarko, S. Yamashita, S. D. Denisov, et al., in: The Thyroid. Fundamental Aspects [in Russian], Omuro-Print, Minsk-Nagasaki (1998), p. 31.

  13. G. A. Brent, New Engl. J. Med., 331, No. 13, 847 (1994).

    Article  CAS  Google Scholar 

  14. E. I. Kononov and F. I. Kurdyumov, Thyroid Hormones, Izd. MGU, Moscow (2004).

    Google Scholar 

  15. C. Laurence, M. J. El Ghomari, J. Y. Le. Questel, et al., J. Chem. Soc., Perkin Trans. 2, 1545 (1998).

  16. M. C. Aragoni, M. Arca, F. Demartin, et al., J. Am. Soc., 124, No. 17, 4538 (2002).

    Article  CAS  Google Scholar 

  17. M. Arca, M. C. Aragoni, F. A. Devillanova, et al., Bioinorg. Chem. Appl., Article ID 58937 (2006), p. 12.

  18. V. Daga, S. K. Hadjikakou, N. Hadjiliadis, et al., Eur. J. Inorg. Chem., 1718 (2002).

  19. C. D. Antoniadis, G. J. Corban, S. K. Hadjikakou, et al., Eur. J. Inorg. Chem., 1635 (2003).

  20. C. D. Antoniadis, S. K. Hadjikakou, N. Hadjiliadis, et al., Eur. J. Inorg. Chem., 4324 (2004).

  21. G. J. Corban, S. K. Hadjikakou, N. Hadjiliadis, et al., Inorg. Chem., 44, No. 23, 8617 (2005).

    Article  CAS  Google Scholar 

  22. F. Cristiani, F. A. Devillanova, F. Isaia, et al., Polyhedron, 14, Nos. 20/21, 2937 (1995).

    Article  CAS  Google Scholar 

  23. M. S. Chernov’yants, E. V. Khokhlov, E. O. Lykova, et al., Izv. Akad. Nauk, Ser. Khim., 6, 1215 (2008).

    Google Scholar 

  24. A. Taurog, M. L. Dorris, and D. R. Doerge, Arch. Biochem. Biophys., 330, 24 (1996).

    Article  CAS  Google Scholar 

  25. V. B. Oza, G. M. Salamonczyk, Z. Guo, et al., J. Am. Chem. Soc., 119, No. 46, 11315 (1997).

    Article  CAS  Google Scholar 

  26. J. Ruf and P. Carayon, Arch. Biochem. Biophys., 445, No. 2, 269 (2006).

    Article  CAS  Google Scholar 

  27. G. Roy and G. Mugesh, Chem. Biodivers., 5, No. 3, 414 (2008).

    Article  CAS  Google Scholar 

  28. A. Taurog, in: The Thyroid, L. E. Braverman and R. D. Utiger (eds.), Philadelphia: Lippincott, Williams & Wilkins, (2000), p. 61.

    Google Scholar 

  29. R. L. Divi and D. R. Doerge, Chem. Res. Toxicol., 9, No. 1, 16 (1996).

    Article  CAS  Google Scholar 

  30. D. R. Doerge, R. L. Divi, J. Deck, et al., Chem. Res. Toxicol., 10, No. 1, 49 (1997).

    Article  CAS  Google Scholar 

  31. D. R. Doerge, H. C. Chang, R. L. Divi, et al., Chem. Res. Toxicol., 11, No. 9, 1098 (1998).

    Article  CAS  Google Scholar 

  32. N. H. Nguyen, J. W. Apriletti, S. T. C. Lima, et al., J. Med. Chem., 45, No. 15, 3310 (2002).

    Article  CAS  Google Scholar 

  33. C. D. Antoniadis, S. K. Hadjikakou, N. Hadjiliadis, et al., Chem. Eur. J., 12, 6888 (2006).

    Article  CAS  Google Scholar 

  34. C. D. Antoniadis, A. J. Blake, S. K. Hadjikakou, et al., Acta Crystallogr., Sect. A, 62, No. 4, 580 (2006).

    Article  Google Scholar 

  35. H. Roohi, A. Ebrahimi, and S. M. Habibi, J. Mol. Struct. (Theochem.), 710, 77 (2004).

    Article  CAS  Google Scholar 

  36. M. S. Chernov’yants and I. V. Burykin, Izv. Akad. Nauk, Ser. Khim., No. 9, 1716 (2009).

  37. D. K. Papayannis and A. M. Kosmas, J. Mol. Struct. (Theochem.), 851, 175 (2008).

    Article  CAS  Google Scholar 

  38. M. C. Aragoni, M. Arca, F. Demartin, et al., Trends Inorg. Chem., 6, 1 (1999).

    CAS  Google Scholar 

  39. F. Cristiani, F. Demartin, F. A. Devillanova, et al., J. Chem. Soc. Dalton. Trans., 3553 (1992).

  40. P. D. Boyle, J. Christie, T. Dyer, et al., J. Chem. Soc., Dalton Trans., 3106 (2000).

  41. M. C. Aragoni, M. Arca, F. A. Devillanova, et al., Coord. Chem. Rev., 184, 271 (1999).

    Article  CAS  Google Scholar 

  42. S. K. Hadjikakou and N. Hadjiliadis, Bioinorg. Chem. Appl., Article ID 60291 (2006), p. 10.

  43. I. E. Parigoridi, G. J. Corban, S. K. Hadjikakou, et al., Dalton Trans., 5159 (2008).

  44. G. J. Corban, C. Antoniadis, S. K. Hadjikakou, et al., Bioinorg. Chem. Appl., Article ID 68542 (2006), p. 5.

  45. H. M. A. Salman, M. M. Abu-Krisha, and H. S. El-Sheshtawy, Can. J. Anal. Sci. Spectr., 49, 282 (2004).

    CAS  Google Scholar 

  46. J. H. Z. dosSantos, I. S. Daga, S. K. Hadjikakou, et al., Spectr. Acta Part A, 58, No. 12, 2725 (2002).

    Article  Google Scholar 

  47. P. D. Boyle and S. M. Godfrey, Coord. Chem. Rev., 223, 265 (2001).

    Article  CAS  Google Scholar 

  48. C. Näther and M. Bolte, Phosphorus, Sulfur and Silicon, 178, No. 3, 453 (2003).

    Article  Google Scholar 

  49. E. D. Raczynska, W. Kosinska, B. Osmialowski, and R. Gawinecki, Chem. Rev., 105, No. 10, 3561 (2005).

    Article  CAS  Google Scholar 

  50. A. R. Katritzky, K. Jug, and D. C. Oniciu, Chem. Rev., 101, No. 5, 1421 (2001).

    Article  CAS  Google Scholar 

  51. D. Moran, K. Sukcharoephon, R. Puchta, et al., J. Org. Chem., 67, No. 25, 9061 (2002).

    Article  CAS  Google Scholar 

  52. F. Bigoli, P. Deplano, M. L. Mercuri, et al., J. Chem. Soc. Dalton Trans., 3583 (1996).

  53. F. Bigoli, P. Deplano, A. Ienco, et al., Inorg. Chem., 38, No. 21, 4626 (1999).

    Article  CAS  Google Scholar 

  54. P. Deplano, J. R. Ferraro, M. L. Mercuri, et al., Coord. Chem. Rev., 188, No. 1, 71 (1999).

    Article  CAS  Google Scholar 

  55. P. Deplano, F. A. Devillanova, J. R. Ferraro, et al., Appl. Spectr., 46, No. 11, 1625 (1992).

    Article  CAS  Google Scholar 

  56. F. Bigoli, P. Deplano, M. L. Mercuri, et al., Can. J. Chem., 73, No. 3, 380 (1995).

    Article  CAS  Google Scholar 

  57. F. van Bolhuis, P. B. Kotter, and T. Migchelsen, Acta Crystallogr., 23, 90 (1967).

    Article  Google Scholar 

  58. F. Bigoli, P. Deplano, F. A. Devillanova, et al., Gazz. Chim. Ital., 124, No. 11, 445 (1994).

    CAS  Google Scholar 

  59. D. S. Cooper, N. Engl. J. Med., 352, No. 19, 905 (2005).

    Article  CAS  Google Scholar 

  60. F. Cristiani, F. Demartin, F. A. Devillanova, et al., Heteroat. Chem., 5, 65 (1994).

    Article  CAS  Google Scholar 

  61. M. Esseffar, W. Bouab, A. Lamsabhi, et al., J. Am. Chem. Soc., 122, No. 10, 2300 (2000).

    Article  CAS  Google Scholar 

  62. M. S. Chernov’yants, E. V. Khokhlov, and G. S. Borodkin, Proc. of the 3rd Intern. Conf. on New Technologies and Applications of Modern Physicochemical Methods for Environmental Studies [in Russian], Rostov-on-Don, 1, 61 (2005).

    Google Scholar 

  63. A. Suszka, J. Chem. Perkin Trans. 2, 531 (1985).

    Article  Google Scholar 

  64. F. Freeman, J. W. Ziller, H. N. Po, M. C. Keindl, et al., J. Am. Chem. Soc., 110, No. 8, 2586 (1988).

    Article  CAS  Google Scholar 

  65. F. H. Herbstein and W. Schwotzer, J. Am. Chem. Soc., 106, 2367 (1984).

    Article  CAS  Google Scholar 

  66. F. Demartin, P. Deplano, F. A. Devillanova, et al., Inorg. Chem., 32, No. 17, 3694 (1993).

    Article  CAS  Google Scholar 

  67. V. V. Zhdankin and P. J. Stang, Chem. Rev., 108, No. 12, 5299 (2008).

    Article  CAS  Google Scholar 

  68. P. J. Stang and V. V. Zhdankin, Chem. Rev., 96, No. 3, 1123 (1996).

    Article  CAS  Google Scholar 

  69. M. S. Chernov’yants, N. V. Aleshina, Z. A. Starikova, et al., Izv. Akad. Nauk, Ser. Khim., in press.

  70. A. V. Vorontsov, Usp. Khim., 77, No. 10, 973 (2008).

    Google Scholar 

  71. E. B. Podgornaya, M. S. Chernov’yants, I. N. Shcherbakov, et al., Zh. Obshch. Khim., 69, No. 1, 109 (1999).

    Google Scholar 

  72. C. C. Simonyan and M. S. Chernov’yants, Zh. Fiz. Khim., 79, No. 11, 2014 (2005).

    Google Scholar 

  73. C. C. Simonyan, M. S. Chernov’yants, and E. O. Lykova, Zh. Fiz. Khim., 79, No. 10, 1814 (2005).

    Google Scholar 

  74. J. Buxeraud, A. B. Absil, J. Claude, et al., Eur. J. Med. Chem., Chim Ther., 20, 43 (1985).

    CAS  Google Scholar 

  75. C. Raby, J. F. Lagorce, A. C. Jambut-Absil, et al., Endocrinology, 126, No. 3, 1683 (1990).

    Article  CAS  Google Scholar 

  76. M. S. Chernov’yants, E. B. Podgornaya, A. I. Pyshchev, et al., Zh. Obshch. Khim., 68, No. 5, 822 (1998).

    Google Scholar 

  77. J. F. Lagorce, J. Buxeraud, A. C. Jambut-Absil, et al., Heterocycles, 31, 1609 (1990).

    Article  CAS  Google Scholar 

  78. F. A. Devillanova and G. Verani, J. Heterocycl. Chem., 16, 945 (1979).

    Article  CAS  Google Scholar 

  79. A. O. Dolinkin, Proc. of the Intern. Congress “Prospect -2007,” Nal’chik, 3, 269 (2007).

    Google Scholar 

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Correspondence to A. O. Dolinkin.

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Original Russian Text Copyright © 2010 by M. S. Chernov’yants and A. O. Dolinkin

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Translated from Zhurnal Strukturnoi Khimii, Vol. 51, No. 6, pp. 1211–1224, November–December, 2010.

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Chernov’yants, M.S., Dolinkin, A.O. Heteroaromatic thioamides: Structure and stability of charge transfer complexes with iodine, antithyroid activity. J Struct Chem 51, 1176–1190 (2010). https://doi.org/10.1007/s10947-010-0178-9

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