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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M. Vieites, P. Smircich, B. Parajòn-Costa, et al., J. Biol. Inorg. Chem., 13, No. 5, 723 (2008).
J. Franklyn, Clin. Med., 3, 11 (2003).
S. Sahasranaman, D. Howard, and S. Roy, Eur. J. Clin. Pharmacol., 64, No. 8, 753 (2008).
Pat. 5945426 US, Ross. Khim. Zh., 19O102 (2000).
A. H. Abdel-Rahman and M. T. Abdel-Aal, Pharmazie, 53, 377 (1998).
Pat. 98112915 Europe, Ross. Khim. Zh., 23O136 (1999).
J. S. Larson, A. M. T. Abdel, E. B. Pedersen, et al., J. Heterocycl. Chem., 38, 679 (2001).
E. A. Sudbeck, C. Mao, T. K. Venkatachalam, et al., Antimicrob. Agents Chemother., 42, No. 12, 3225 (1998).
C. Laurence, M. J. El Ghomari, and M. Berthelot, J. Chem. Soc., Perkin Trans 2, 1163 (1998).
C. Laurence, M. J. El Ghomari, and Lucon M., J. Chem. Soc., Perkin Trans 2, 1159 (1998).
W. M. Kettyle and R. A. Arky, Endocrine Pathophysiology, Lippincott-Raven, Philadelphia (1998).
A. I. Kubarko, S. Yamashita, S. D. Denisov, et al., in: The Thyroid. Fundamental Aspects [in Russian], Omuro-Print, Minsk-Nagasaki (1998), p. 31.
G. A. Brent, New Engl. J. Med., 331, No. 13, 847 (1994).
E. I. Kononov and F. I. Kurdyumov, Thyroid Hormones, Izd. MGU, Moscow (2004).
C. Laurence, M. J. El Ghomari, J. Y. Le. Questel, et al., J. Chem. Soc., Perkin Trans. 2, 1545 (1998).
M. C. Aragoni, M. Arca, F. Demartin, et al., J. Am. Soc., 124, No. 17, 4538 (2002).
M. Arca, M. C. Aragoni, F. A. Devillanova, et al., Bioinorg. Chem. Appl., Article ID 58937 (2006), p. 12.
V. Daga, S. K. Hadjikakou, N. Hadjiliadis, et al., Eur. J. Inorg. Chem., 1718 (2002).
C. D. Antoniadis, G. J. Corban, S. K. Hadjikakou, et al., Eur. J. Inorg. Chem., 1635 (2003).
C. D. Antoniadis, S. K. Hadjikakou, N. Hadjiliadis, et al., Eur. J. Inorg. Chem., 4324 (2004).
G. J. Corban, S. K. Hadjikakou, N. Hadjiliadis, et al., Inorg. Chem., 44, No. 23, 8617 (2005).
F. Cristiani, F. A. Devillanova, F. Isaia, et al., Polyhedron, 14, Nos. 20/21, 2937 (1995).
M. S. Chernov’yants, E. V. Khokhlov, E. O. Lykova, et al., Izv. Akad. Nauk, Ser. Khim., 6, 1215 (2008).
A. Taurog, M. L. Dorris, and D. R. Doerge, Arch. Biochem. Biophys., 330, 24 (1996).
V. B. Oza, G. M. Salamonczyk, Z. Guo, et al., J. Am. Chem. Soc., 119, No. 46, 11315 (1997).
J. Ruf and P. Carayon, Arch. Biochem. Biophys., 445, No. 2, 269 (2006).
G. Roy and G. Mugesh, Chem. Biodivers., 5, No. 3, 414 (2008).
A. Taurog, in: The Thyroid, L. E. Braverman and R. D. Utiger (eds.), Philadelphia: Lippincott, Williams & Wilkins, (2000), p. 61.
R. L. Divi and D. R. Doerge, Chem. Res. Toxicol., 9, No. 1, 16 (1996).
D. R. Doerge, R. L. Divi, J. Deck, et al., Chem. Res. Toxicol., 10, No. 1, 49 (1997).
D. R. Doerge, H. C. Chang, R. L. Divi, et al., Chem. Res. Toxicol., 11, No. 9, 1098 (1998).
N. H. Nguyen, J. W. Apriletti, S. T. C. Lima, et al., J. Med. Chem., 45, No. 15, 3310 (2002).
C. D. Antoniadis, S. K. Hadjikakou, N. Hadjiliadis, et al., Chem. Eur. J., 12, 6888 (2006).
C. D. Antoniadis, A. J. Blake, S. K. Hadjikakou, et al., Acta Crystallogr., Sect. A, 62, No. 4, 580 (2006).
H. Roohi, A. Ebrahimi, and S. M. Habibi, J. Mol. Struct. (Theochem.), 710, 77 (2004).
M. S. Chernov’yants and I. V. Burykin, Izv. Akad. Nauk, Ser. Khim., No. 9, 1716 (2009).
D. K. Papayannis and A. M. Kosmas, J. Mol. Struct. (Theochem.), 851, 175 (2008).
M. C. Aragoni, M. Arca, F. Demartin, et al., Trends Inorg. Chem., 6, 1 (1999).
F. Cristiani, F. Demartin, F. A. Devillanova, et al., J. Chem. Soc. Dalton. Trans., 3553 (1992).
P. D. Boyle, J. Christie, T. Dyer, et al., J. Chem. Soc., Dalton Trans., 3106 (2000).
M. C. Aragoni, M. Arca, F. A. Devillanova, et al., Coord. Chem. Rev., 184, 271 (1999).
S. K. Hadjikakou and N. Hadjiliadis, Bioinorg. Chem. Appl., Article ID 60291 (2006), p. 10.
I. E. Parigoridi, G. J. Corban, S. K. Hadjikakou, et al., Dalton Trans., 5159 (2008).
G. J. Corban, C. Antoniadis, S. K. Hadjikakou, et al., Bioinorg. Chem. Appl., Article ID 68542 (2006), p. 5.
H. M. A. Salman, M. M. Abu-Krisha, and H. S. El-Sheshtawy, Can. J. Anal. Sci. Spectr., 49, 282 (2004).
J. H. Z. dosSantos, I. S. Daga, S. K. Hadjikakou, et al., Spectr. Acta Part A, 58, No. 12, 2725 (2002).
P. D. Boyle and S. M. Godfrey, Coord. Chem. Rev., 223, 265 (2001).
C. Näther and M. Bolte, Phosphorus, Sulfur and Silicon, 178, No. 3, 453 (2003).
E. D. Raczynska, W. Kosinska, B. Osmialowski, and R. Gawinecki, Chem. Rev., 105, No. 10, 3561 (2005).
A. R. Katritzky, K. Jug, and D. C. Oniciu, Chem. Rev., 101, No. 5, 1421 (2001).
D. Moran, K. Sukcharoephon, R. Puchta, et al., J. Org. Chem., 67, No. 25, 9061 (2002).
F. Bigoli, P. Deplano, M. L. Mercuri, et al., J. Chem. Soc. Dalton Trans., 3583 (1996).
F. Bigoli, P. Deplano, A. Ienco, et al., Inorg. Chem., 38, No. 21, 4626 (1999).
P. Deplano, J. R. Ferraro, M. L. Mercuri, et al., Coord. Chem. Rev., 188, No. 1, 71 (1999).
P. Deplano, F. A. Devillanova, J. R. Ferraro, et al., Appl. Spectr., 46, No. 11, 1625 (1992).
F. Bigoli, P. Deplano, M. L. Mercuri, et al., Can. J. Chem., 73, No. 3, 380 (1995).
F. van Bolhuis, P. B. Kotter, and T. Migchelsen, Acta Crystallogr., 23, 90 (1967).
F. Bigoli, P. Deplano, F. A. Devillanova, et al., Gazz. Chim. Ital., 124, No. 11, 445 (1994).
D. S. Cooper, N. Engl. J. Med., 352, No. 19, 905 (2005).
F. Cristiani, F. Demartin, F. A. Devillanova, et al., Heteroat. Chem., 5, 65 (1994).
M. Esseffar, W. Bouab, A. Lamsabhi, et al., J. Am. Chem. Soc., 122, No. 10, 2300 (2000).
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).
A. Suszka, J. Chem. Perkin Trans. 2, 531 (1985).
F. Freeman, J. W. Ziller, H. N. Po, M. C. Keindl, et al., J. Am. Chem. Soc., 110, No. 8, 2586 (1988).
F. H. Herbstein and W. Schwotzer, J. Am. Chem. Soc., 106, 2367 (1984).
F. Demartin, P. Deplano, F. A. Devillanova, et al., Inorg. Chem., 32, No. 17, 3694 (1993).
V. V. Zhdankin and P. J. Stang, Chem. Rev., 108, No. 12, 5299 (2008).
P. J. Stang and V. V. Zhdankin, Chem. Rev., 96, No. 3, 1123 (1996).
M. S. Chernov’yants, N. V. Aleshina, Z. A. Starikova, et al., Izv. Akad. Nauk, Ser. Khim., in press.
A. V. Vorontsov, Usp. Khim., 77, No. 10, 973 (2008).
E. B. Podgornaya, M. S. Chernov’yants, I. N. Shcherbakov, et al., Zh. Obshch. Khim., 69, No. 1, 109 (1999).
C. C. Simonyan and M. S. Chernov’yants, Zh. Fiz. Khim., 79, No. 11, 2014 (2005).
C. C. Simonyan, M. S. Chernov’yants, and E. O. Lykova, Zh. Fiz. Khim., 79, No. 10, 1814 (2005).
J. Buxeraud, A. B. Absil, J. Claude, et al., Eur. J. Med. Chem., Chim Ther., 20, 43 (1985).
C. Raby, J. F. Lagorce, A. C. Jambut-Absil, et al., Endocrinology, 126, No. 3, 1683 (1990).
M. S. Chernov’yants, E. B. Podgornaya, A. I. Pyshchev, et al., Zh. Obshch. Khim., 68, No. 5, 822 (1998).
J. F. Lagorce, J. Buxeraud, A. C. Jambut-Absil, et al., Heterocycles, 31, 1609 (1990).
F. A. Devillanova and G. Verani, J. Heterocycl. Chem., 16, 945 (1979).
A. O. Dolinkin, Proc. of the Intern. Congress “Prospect -2007,” Nal’chik, 3, 269 (2007).
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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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DOI: https://doi.org/10.1007/s10947-010-0178-9