3-Amino-5-phenoxythiophenes: Syntheses and structure-function studies of a novel class of inhibitors of cellular L-triiodothyronine uptake

Journal of Medicinal Chemistry

Volumn 42, Issue 10, 1999, Pages 1849-1854

  Briel, Detlef ^a   Pohlers, Dirk ^a   Uhlig, Mathias ^a   Vieweg, Silke ^a   Scholz, Gerhard H ^a   Thormann, Michael ^a   Hofmann, Hans Jörg ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 5 PHENOXYTHIOPHENE DERIVATIVE; LIOTHYRONINE; PREALBUMIN; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HEPG2; CYCLIZATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HORMONE TRANSPORT; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TRIIODOTHYRONINE; TUMOR CELLS, CULTURED;

EID: 0033587104     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980288r     Document Type: Article

References (38)

1. Davis, P. J. Cellular Actions of Thyroid Hormones. In Werner & Ingbar's The Thyroid; Braverman, L. E., Utiger, R. D., Eds.; Lippincott: Philadelphia, 1991; pp 190-203.
2. Oppenheimer, J. H.; Schwartz, H. L.; Mariash, W. B.; Kinlaw, W. B.; Wong, N. C. W.; Freake, H. C. Advances in Our Understanding of Thyroid Hormone Action at the Cellular Level. Endocr. Rev. 1987, 8, 288-308.
3. Meyer-Gessner, M.; Benker, G.; Lederbogen, S.; Olbricht, T.; Reinwein, D. Antithyroid drug-induced agranulocytosis: clinical experience with 10 patients treated at one institution and review of the literature. J. Endocrinol. Invest. 1994, 17, 29-36.
4. Chalmers, D. K.; Scholz, G. H.; Topliss, D. J.; Kolliniatis, E.; Munro, S. L. A.; Craik, D. J.; Iskander, M. N.; Stockigt, J. R. Thyroid Hormone Uptake by Hepatocytes: Structure-Activity Relationships of Phenylanthranilic Acids with Inhibitory Activity. J. Med. Chem. 1993, 36, 1272-1277.
5. 125I]-Triidothyronine Accumulation into Human Liver, Human Neuroblasts, and Rat Pituitary Cell Lines. Endocrinology 1992, 130, 1211-1216.
6. Kragie, L.; Forrester, M. L.; Cody, V.; McCourt, M. Computer-Assisted Molecular Modeling of Benzodiazepine and Thyromimetic Inhibitors of the HepG2 Iodothyronine Membrane Transporter. Mol. Endocrinol. 1994, 8, 382-391.
7. Topliss, D. J.; Scholz, G. H.; Kolliniatis, E.; Barlow, J. W.; Stockigt, J. R. Influence of Calmodulin Antagonists and Calcium Channel Blockers on T3 Uptake by Rat Hepatoma and Myoblast Cell Lines. Metabolism 1993, 42, 376-380.
8. Scholz, G. H.; Vieweg, S.; Uhlig, M.; Thormann, M.; Klossek, P.; Goldmann, S.; Hofmann, H.-J. Inhibition of Thyroid Hormone Uptake by Calcium Antagonists of the Dihydropyridine Class. J. Med. Chem. 1997, 40, 1530-1538.
9. Yokoyama, N.; Walker, G. N.; Main, A. J.; Stanton, J. L.; Morrissey, M. M.; Boehm, C.; Engle, A.; Neubert, A. D.; Wasvary, J. M.; Stephan, Z. F.; Steele, R. E. Synthesis and Structure-Activity Relationships of Oxamic Acid and Acetic Acid Derivatives Related to L-Thyronine. J. Med. Chem. 1995, 38, 665-707.
10. Jorgensen, E. C. Structure-Activity Relations of Thyroxine Analogues. Pharmacol. Ther., Part B 1976, 2, 661-682.
11. Dietrich, S. W.; Bolger, M. B.; Kollman, P. A.; Jorgensen, E. C. Thyroxine Analogues. 23. Quantitative Structure-Activity Correlation Studies of In Vivo and In Vitro Thyromimetic Activities. J. Med. Chem. 1977, 20, 863-880.
12. Andrea, T. A.; Dietrich, S. W.; Murray, W. J.; Kollmann, P. A.; Jorgensen, E. C. A Model for Thyroid Hormone-Receptor Interactions. J. Med. Chem. 1979, 22, 221-232.
13. Bolger, M. B.; Jorgensen, E. C. Molecular Interactions Between Thyroid Hormone Analogues and the Rat Liver Nuclear Receptor. J. Biol. Chem. 1980, 255, 10271-10278.
14. Cody, V. Thyroid Hormones Interactions: Molecular Conformation, Protein Binding and Hormone Action. Endocr. Rev. 1980, 1, 140-161.
15. Cody, V. Distal Conformation of Thyroid Hormones. Crystal and Molecular Structure of 3,5,3′-Triiodo-L-Thyronine Methyl Ester. J. Med. Chem. 1975, 18, 126-129.
16. Kollman, P. A.; Murray, W. J.; Nuss, M. E.; Jorgensen, E. C.; Rothenberg, S. Molecular Orbital Studies of Thyroid Hormone Analogues. J. Am. Chem. Soc. 1973, 95, 8518-8525.
17. Hofmann, H.-J.; Thieroff, K. Quantenchemische Berechnungen zur konformativen Struktur konjugierter Biomoleküle. (Quantumchemical Calculations on the Conformation of Conjugated Biomolecules.) Pharmazie 1975, 30, 586-589.
18. Blaney, J. M.; Weiner, P. K.; Dearing, A.; Kollman, P. A.; Jorgensen, E. C.; Oatley, S. J.; Burridge, J. M.; Blake, C. C. F. Molecular Mechanics Simulation of Protein-Ligand Interactions: Binding of Thyroid Hormone Analogues to Prealbumin. J. Am. Chem. Soc. 1982, 104, 6424-6434.
19. Blaney, J. M.; Jorgensen, E. C.; Conolly, M. L.; Ferrin, T. E.; Langridge, R.; Oatley, S. J.; Burridge, J. M.; Blake, C. C. F. Computer Graphics in Drug Design: Molecular Modelling of Thyroid-Hormone-Prealbumin Interactions. J. Med. Chem. 1982, 25, 785-790.
20. Cheung, E. N. Y. Thyroid Hormon Action: Determination of Hormone-Receptor Interaction Using Structural Analogues and Molecular Modeling. Trends Pharmacol. Sci. 1985, 6, 31-34.
21. Gompper, R.; Kutter, E.; Töpfl, W. Neue Thiophene und Thieno-[2,3-b]thiophene. (New Thiophenes and Thieno[2,3-b]thiophenes.) Liebigs Ann. Chem. 1962, 659, 90-101.
22. Briel, D. Neue Heterocyclensysteme aus Thiophen-2-thiolen -Synthese und biologische Aktivität. (New Heterocyclic Systems with Thiophene-2-thiol - Synthesis and Biological Activity.) Pharmazie 1990, 45, 895-899.
23. Briel, D.; Wagner, G.; Will, S.; Lohmann, D.; Laban, G. Verfahren zur Herstellung von substituierten Thiophen-2-thiolen. (Procedure for the Preparation of Substituted Thiophene-2-thiols.) DD-Patent No. 276 283, 1990; Chem. Abstr. 1991, 114, P81567n.
24. Briel, D.; Wagner, G.; Will, S.; Lohmann, D.; Laban, G. Verfahren zur Herstellung von substituierten Thiophen-2-thiolen. (Procedure for the Preparation of Substituted Thiophene-2-thiols.) DD-Patent No. 276 283, 1990; Chem. Abstr. 1991, 114, P81567n.
25. Dolman, H.; Kuipers, J. Eur. Patent Appl. No. 234 622, 1987; Chem. Abstr. 1988, 109, P110245k.
26. Dolman, H.; Kuipers, J. Eur. Patent Appl. No. 234 622, 1987; Chem. Abstr. 1988, 109, P110245k.
27. Briel, D.; Wagner, G.; Lohmann, D. Verfahren zur Herstellung von in 5-Position verschiedenartig substituierten 3-Aminothiophen-4-carbonitrilen. (Procedure for the Preparation of 5-Substituted 3-Aminothiophene-4-carbonitriles.) DD-Patent No. 275 870, 1988; Chem. Abstr. 1990, 113, P131988c.
28. Briel, D.; Wagner, G.; Lohmann, D. Verfahren zur Herstellung von in 5-Position verschiedenartig substituierten 3-Aminothiophen-4-carbonitrilen. (Procedure for the Preparation of 5-Substituted 3-Aminothiophene-4-carbonitriles.) DD-Patent No. 275 870, 1988; Chem. Abstr. 1990, 113, P131988c.
29. Briel, D. Synthese von Thieno-Heterocyclen ausgehend von substituierten S-Methylthio-thiophen-4-carbonitrilen. (Synthesis of Thieno Heterocycles with Substituted S-Methylthio-thiophene-4-carbonitrile.) Pharmazie 1998, 53, 227-231.
30. Hehre, W. J.; Radom, L.; v. R. Schleyer, P.; Pople, J. A. Ab Initio Molecular Orbital Theory; J. Wiley: New York, 1986.
31. Goodsell, D. S.; Morris, G. M.; Olson, A. J. Docking of Flexible Ligands: Applications of AutoDock. J. Mol. Recognit. 1996, 9, 1-5.
32. Morris, G. M.; Goodsell, D. S.; Huey, R.; Olson, A. J. Distributed automated docking of flexible ligands to proteins: Parallel applications of AutoDock 2.4. J. Comput.-Aided Mol. Des. 1996, 10, 293-304.
33. Hamilton, J. A.; Steinrauf, L. K.; Braden, B. C.; Liepnieks, J. J.; Benson, M. D.; Holmgren, G.; Sandgren, O.; Steen, L. The X-ray Crystal Structure Refinements of Normal Human Transthyretin and the Amyloidogenic ValMet Variant at 1.7 Å Resolution. J. Biol. Chem. 1993, 268, 2416-242.
34. Wojtczak, A. Crystal structure of rat transthyretin at 2.5 Å resolution: First report on a unique tetrameric structure. Acta Biochim. Pol. 1997, 44, 505-517.
35. Wojtczak, A.; Cody, V.; Luft, J. R.; Pangborn, W. Structures of human transthyretin complexed with thyroxine at 2.0 Å resolution and 3′,5′-dinitro-N-acetyl-L-thyronine at 2.2 Å resolution. Acta Crystallogr. 1996, D52, 758-765.
36. SPARTAN, version 4.1; Wavefunction Inc.: Irvine, 1995.
37. Clog P, version 1.0.0; BioByte Corp.: Claremont, 1995.
38. QUANTA96; Molecular Simulations Inc.: San Diego, 1996.