Abstract
The thyroid hormones, thyroxine (T4; 1) and 3,5,3′-triiodothyronine (T3; 2) are
necessary for the maintenance of normal growth and metabolism in a variety of organisms [1]. Since their isolation and structure elucidation in the first half of this century many theories regarding their mechanism of action have been proposed [2]. Also, because of the rather simple nature of their structure much work has been done on structural analogs of the hormones and, therefore, much is known about the structural features necessary for activity. However, no theory has yet evolved which ties together this detailed understanding of the structural requirements for hormone activity and those biochemical events governed by the hormones. It was thought that a molecular orbital study comparing the endogenous hormones and a highly active methylene-bridged analog 3,5-diiodo4-(4′-hydroxy-3′-iodobenzyl)-DL-phenylalanine (MB-T3) with less active analogs, 3,5-diiodo-4-(3′-iodo-4′-aminophenoxy)-DL-phenyl-alanine (4′-NH2) and 3,5,3′-trimethyl-L-thyronine (Me3), might reveal characteristics of the structural features which would lead to deductions regarding the functional role of the hormones.
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References
Pitt-Rivers R. and Tata, J. R., The Thyroid Hormones, Pergamon Press, Los Angeles, Chap. 5. 1959.
Tata, J. R., Ann. Rep. Progr. Chem., Chem. Soc., London, 60, SO1 (1963)
Hoch, F.L., Physiol. Rev. 42, 605 (1962)
Wolff E. C. and Wolff, J., in: Pitt-Rivers R. and Trotter, W. R. (Eds.), The Thyroid Gland Vol. 1, Butterworths, Washington, p. 236, (1964).
Pople, J. A., Santry D. P. and Segal, G. A., J. chem. Phys. 42, S 129 (1965)
Pople, J. A. and Segal, G. A. ibid., 43, S 136 (1965).
The CNDO/2 calculations were carried out with QCPE program 91.
Handbook of Organic Structural Analysis, (Yukawa, Y. Ed.) W. A. Benjamin Inc., New York, 1965, Pople J. A. and Gordon, M., J. amer. chem. Soc. 89. 4253 (1967).
Deb, B. M. and Coulson, C. A., J. chem. Soc. (A) 958 (1971).
For further details on this point, please contact the author.
Katon, J.E. Feairheller, W.R. Jr. and Lippincott, E.R., J. mol. Spectr. 13, 72 (1964).
Pople, J. A. and Beveridge, D. L. Approximate Molecular Orbital Theory, McGraw-Hill, New York, 1970
Kollman, P.A. and Allen, L.C., Chem. Rev. 72, 283 (1972).
Cody, V. and Duax, W.L. Biochem. biophys. Res. Commun. 52, 430 (1973)
Cody, V. and Duax, W.L., Science. 181, 757 (1973).
Kier, L.B. and Hoyland, J.R., J. med. Chem. 13, 1182 (1970).
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Kollman, P.A., Murray, W.J., Nuss, M.E. (1976). Theoretical Studies of Thyroid Hormone Analogs. In: Tichý, M. (eds) Quantitative Structure-Activity Relationships. Experientia Supplementum, vol 23. Birkhäuser, Basel. https://doi.org/10.1007/978-3-0348-5795-6_28
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DOI: https://doi.org/10.1007/978-3-0348-5795-6_28
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