Abstract
This review considers the methods of synthesis of thyroxine and triiodothyronine, which were developed on the basis of hypothetical models of their biosynthesis in the organism. Most of such methods are based on the use of highly active derivatives of phenols or quinones (4-hydroxy-3,5-diiodophenylpyruvic acid, iodine-containing derivatives of spiro-4-epoxycyclohexadienone, 2,4,6-tri-tert-butylphenol, etc.) as arylating agents. Condensation of these compounds with 3,5-derivatives of tyrosine results in the formation of substituted diaryl esters, representing thyroid hormones or their analogs. Some of the proposed methods are highly effective and lead to high yields of thyroid hormones, which can be used as parent drug substances.
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L. E. B. Utiger and R. V. Utiger, The Thyroid: A Fundamental and Clinical Text, Lippincott, Philadelphia (1991).
M. D. Mashkovskii, Drugs [in Russian], Torsing, Kharkov (1998), Vol. 2, p. 11.
J. H. Oppennheimer, J. W. Apriletti, and H. H. Samuels, Molecular Basis of Thyroid hormone action, Academic, New York (1983).
S. F. Engelken and R. P. Eaton, Atherosclerosis, 38, 177–188 (1981).
P. Hansson, S. Valdemarsson, and P. Nilsson-Ehhle, Horm. Metab. Res., 115, 449–452 (1983).
B. Blank, F. R. Pfeiffer., C. M. Greenberg, and J. F. Kerwin, J. Med. Chem., 6, 554–560 (1963).
A. H. Unterwood, G. C. Emmlett., D. Ellis, et al., Nature, 324, 425–429 (1986).
N. Yokoyama, G. N. Walker, A. J. Main, et al., J. Med. Chem., 38, 695–707 (1995).
P. D. Leeson, J. C. Emmlett, V. D. Shah, et al., J. Med. Chem., 32, 320–336 (1989).
D. M. B. Hickley, P. D. Leeson, R. Novelli, et al., J. Chem. Soc. Perkin Trans., 3103–3111 (1988).
P. D. Leeson, G. M. Benson, J. C. Emmlett, et al., J. Med. Chem., 31, 37–54 (1988).
H. A. I. Yoshihara, G. Chiellini, T. J. Mitchison, and T. S. Scanlan, Bioorg. Med. Chem., 6, 1179–1183 (1998).
J. D. Baxter, W. H. Dillmann, B. L. West, et al., J. Steroid. Chem. Mol. Biol., 76, 31–39 (2001).
M. A. Lasar, Endokrine Rev., 14, 184–197 (1993).
G. Chiellini, N.-H. Nguyen, J. W. Apriletti, et al., Bioorg. Med. Chem., 10, 333–346 (2002).
A. H. Taylor, Z. F. Stefan, R. E. Steele, et al., Mol. Pharmacol., 52, 542–548 (1997).
R. E. Steele, J. M. Wasvary, B. N. Dardik, et al., Atherosclerosis, 109, 89–90 (1994).
C. R. Harington and G. Barger, Biochem. J., 21, 169–181 (1927).
J. Gross and R. Pitt-Rivers, Biochem. J., 53, 645–650 (1953).
J. Roshe, R. Michel, and W. Wolf, C. R. Acad. Sci (Paris), 240, 251–253 (1955).
P. M. Kochergin, R. M. Palei, A. N. Kravchenko, and E. V. Popova, Khim.-Farm. Zh., 24(1), 43–49 (1990).
M. V. Ugryumov, Mechanisms of Neuroendocrine Regulation [in Russian], Nauka, Moscow (1999), pp. 167–170.
J. E. Morley, Endocrinol. Rev., 2, 312–320 (1981).
M. Nakamura, I. Yamazaki, and S. Ohtaki, Thyroperoxidase and Thyroid Autoimmunity, P. Carayon, J. Ruf (eds.), Colloque INSERM / John Libbey eurotext, 207, Paris (1990), pp. 77–83.
B. Corvilain, C. Gerard, E. Raspe, et al., Thyroperoxidase and Thyroid Autoimmunity, P. Carayon, J. Ruf (eds.), Colloque INSERM / John Libbey eurotext, 207, Paris (1990), pp. 33–41.
S. G. Venkatech and V. Despande, Endocrinology, 122, 5–17 (1999).
J. Nunez and J. Pommier, Vitam. Horm., 39, 175–183 (1982).
P. Mutcebeher, J. Physiol. Chem., 261, 253–257 (1939).
R. Pitt-Rivers, Biochem J., 43, 223–231 (1948).
G. Hillman, B. Keil B, and P. Tashimi, Z. Naturforsh., 16, 28–32 (1961).
R. I. Meltzer and R. J. Stanaback, J. Org. Chem., 26, 1977–1979 (1961).
K. Sorimashi and H. J. Cahnmann, Endocrinology, 101, 1276–1280 (1977).
V. P. Martinovich, N. A. Fil’chenkov, and O. V. Sviridov, Vest. Nat. Akad. Nav. Bel., Ser. Khim. Nav., No. 1, 56–63 (2003).
A. Nishigawa, H. Kon, J. H. Cahnmann, and T. Matsuura, J. Org. Chem., 33, 157–162 (1968).
A. Nishigawa, J. N. Cahnmann, H. Kon, and T. Matsuura, Biochemistry, 7, 388–397 (1968).
F. Blasi, F. Fragomele, and I. Corelli, Endocrinology, 85, 542–551 (1969).
V. B. Oza, G. M. Salamonchyk, Z. Guo, and J. C. Shi, J. Am. Chem. Soc., 119, 11315–11316 (1997).
H. Ogawara and J. H. Cahnmann, Biochim. Biophys. Acta, 257, 328–338 (1972).
T. Shiba and J. H. Cahnmann, J. Org. Chem., 29, 1652–1658 (1964).
J. H. Cahnmann and K. Funakoshi, Biochemistry, 9, 90–98 (1970).
G. M. Salamonchyk, V. B. Oza, and C. J. Sih, Tetrahedron Lett., 38, 6965–6968 (1997).
E. Alder, K. Holmberg, and L.-O. Ryrfors, Acta Chem. Scand., B 28, 883–887 (1974).
V. P. Martinovich, Ya. M. Katok, N. A. Fil’chenkov, and O. V. Sviridov, Vest. Nat. Akad. Nav. Bel., Ser. Khim. Nav., No. 1, 85–92 (2004).
A. Taurog, M. Dorris, and D. R. Doerge, Arch. Biochem. Biophys., 315, 82–89 (1994).
J. H. Cahnmann, J. Pommier, and Nunez, Proc. Natl. Acad. Sci USA, 74, 5333–5335 (1977).
Y. Ma and C. J. Sih, Tetrahedron Lett., 40, 9211–9214 (1999).
R. Pitt-Rivers and A. T. James, Biochem. J., 70, 173–176 (1958).
N. V. Bell, W. R. Bowman, P. F. Coe, et al., Can. J. Chem., 75, 873–883 (1997).
T. Matsuura and A. Nishigawa, J. Org. Chem., 27, 3072–3075 (1962).
A. Hutinec, A. Ziogas, and A. Rieker, Amino Acids, 11, 345–366 (1996).
D. M. B. Hickley, P. M. Leeson, S. D. Carter, et al., J. Chem. Soc. Perkin Trains., 3097–3102 (1988).
L. J. Degroot and H. Niepomniszcze, Metabolism, 26, 665–718 (1977).
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 9, pp. 45–49, September, 2006.
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Martinovich, V.P., Sviridov, O.V. Obtaining thyroid hormones by chemical methods based on biosynthesis modeling (a review). Pharm Chem J 40, 507–512 (2006). https://doi.org/10.1007/s11094-006-0166-8
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DOI: https://doi.org/10.1007/s11094-006-0166-8