Retinoic acid receptor β,γ-selective ligands: Synthesis and biological activity of 6-substituted 2-naphthoic acid retinoids

Journal of Medicinal Chemistry

Volumn 39, Issue 12, 1996, Pages 2411-2421

  Yu, Kuo Long ^a   Spinazze, Patrick ^a   Ostrowski, Jacek ^a   Currier, Stephen J ^a   Pack, Edward J ^a   Hammer, Laura ^a   Roalsvig, Thor ^a   Honeyman, Jomary A ^a   Tortolani, David R ^a   Reczek, Peter R ^a   Mansuri, Muzammil M ^a   Starrett Jr , John E ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 [(5,6,7,8 TETRAHYDRO 5,5,8,8 TETRAMETHYL 2 NAPHTHALENYL)(HYDROXYIMINO)METHYL] 2 NAPHTHALENECARBOXYLIC ACID; RETINOIC ACID; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOASSAY; DRUG ACTIVITY; DRUG SYNTHESIS; GENE CONTROL; LIGAND BINDING; NUCLEAR OVERHAUSER EFFECT; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; TRANSACTIVATION;

BINDING, COMPETITIVE; DRUG DESIGN; GENES, REPORTER; HELA CELLS; HUMANS; LIGANDS; MOLECULAR STRUCTURE; NAPHTHALENES; RECEPTORS, RETINOIC ACID; RECOMBINANT FUSION PROTEINS; RETINOIDS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TRANS-ACTIVATION (GENETICS); TRETINOIN;

EID: 15844376848     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9502293     Document Type: Article

References (32)

1. The Retinoids, Biology, Chemistry, and Medicine; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Raven Press: New York, 1994.
2. Lever, L.; Marks, R. Topical Retinoid Treatment For Skin Cancer: A Review. Skin Pharmacol. 1991, 4, 125-131.
3. Smith, M. A.; Parkinson, D. R.; Cheson, B. D.; Friedman, M. A. Retinoids In Cancer Therapy. J. Clin. Oncol. 1992, 10, 839-864.
4. Lippman, S. M.; Kessler, J. F.; Meyskens, F. L., Jr. Retinoids as Preventive and Therapeutic Anticancer Agents (Part I). Cancer Treatment Rep. 1987, 71, 391-405 (493-515).
5. Leid, M.; Kastner, P.; Chambon, P. Multiplicity Generates Diversity in the Retinoic Acid Signalling Pathways. Trends Biochem. Sci. 1992, 17, 427-433.
6. Mangelsdorf, D. J.; Ong, E. S.; Dyck, J. A.; Evans, R. M. Nuclear Receptor That Identifies A Novel Retinoic Acid Response Pathway. Nature 1990, 345, 224-229.
7. Zelent, A.; Krust, A.; Petkovich, M.; Kastner, P.; Chambon, P. Cloning of Murine α and β Retinoic Acid Receptors and A Novel Receptor γ Predominantly Expressed in Skin. Nature 1989, 339, 714-717.
8. Rees, J. L.; Daly, A. K.; Redfern, C. P. F. Differential Expression Of The α and β Retinoic Acid Receptors In Tissues of The Rat. Biochem. J. 1989, 259, 917-919.
9. Elder, J. T.; Fisher, G. J.; Zhang, Q.-Y.; Eisen, D.; Krust, A.; Kastner, P.; Chambon, P.; Voorhees, J. J. Retinoic acid Receptor Gene Expression in Human Skin. J. Invest. Dermatol. 1991, 96, 425-433.
10. Bernard, B. A.; Bernardon, J. M.; Delescluse, C.; Martin, B.; Lenoir, M. C.; Maignan, J.; Charpentier, B.; Pilgrim, W. R.; Reichert, U.; Shroot, B. Identification of Synthetic Retinoids With Selectivity for Human Nuclear Retinoic Acid Receptor γ. Biochem. Biophys. Res. Commun. 1992, 186, 977-983.
11. Graupner, G.; Malle, G.; Maignan, J.; Lang, G.; Prunieras, M.; Pfahl, M. 6′-Substituted Naphthalene-2-carboxylic Acid Analogs, A New Class Of Retinoic Acid Receptor Subtype-specific Ligands. Biochem. Biophys. Res. Commun. 1991, 179, 1554-1561.
12. Lehmann, J. M.; Dawson, M. I.; Hobbs, P. D.; Husmann, M.; Pfahl, M. Identification of Retinoids With Nuclear Receptor Subtype-selective Activities. Cancer Res. 1991, 51, 4804-4809.
13. Lehmann, J. M.; Jong, L.; Fanjul, A.; Cameron, J. F.; Lu, X. P.; Dawson, M. I.; Pfahl, M. Retinoids Selective for Retinoid X Receptor Response Pathway. Science 1992, 258, 1944-1946.
14. Delescluse, C.; Cavey, M. T.; Martin, B.; Bernard, B. A.; Reichert, U.; Maignan, J.; Darmon, M.; Shroot, B. Selective High Affinity Retinoic Acid Receptor α or β-γ Ligands. Mol. Pharmacol. 1992, 40, 556-562.
15. Reczek, P. R.; Ostrowski, J.; Yu, K.-L.; Chen, S.; Hammer, L.; Roalsvig, T.; Starrett, J. E.; Driscoll, J.; Whiting, G.; Spinazze, P.; Tramposch, K. M.; Mansuri, M. M. The role of retinoic acid receptor gamma and the Rhino mouse and rabbit irritation models of retinoid activity. Skin Pharmacol. 1995, 8, 1-4.
16. Maignan, J.; les Gonesse, T.; Lang, G.; Gratien, S.; Malle, G.; sur Morin, V.; Restle, S.; Boise, A. S.; Shroot, B. Bicyclic Naphthalenic Derivatives, A Process for Preparing The Same and Human or Veterinary Medicines and Cosmetic Compositions Containing Said Derivatives. U.S. Patent 4,826,969, 1989.
17. Berkowitz, D. B.; Danishefsky, S. J. Enzymatic Resolution of Racemic Glycals: An Application of the Wong Acylation Method. Tetrahedron Lett. 1991, 32, 5497-5500.
18. Pirkle, W.; Sikkenga, D. L. The Use of Chiral Solvating Agents for Nuclear Magnetic Resonance Determination of Enantiomeric Purity and Absolute Configuration of Lactones. Consequences of Three-Point Interactions. J. Org. Chem. 1977, 42, 1370-1374.
19. Gao, Q.; Yu, K.-L.; Mansuri, M.; Kerns, E.; Starrett, J. E. Structure of Methyl 6-[(4-Bromobenzoyloxy)-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)- methyl]-2-naphthalene-2-carboxylate. Acta Crystallogr. C 1995, C51, 1672-1675.
20. Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T.; Matthews, D. P.; McCarthy, J. R. Difluoromethyldiphenylphosphine Oxide. A New Reagent for Conversion of Carbonyl Compounds to 1,1-Difluoroolefins. Tetrahedron Lett. 1990, 31, 5571-5574.
21. Dolle, R. E.; Schmidt, S. J.; Kruse, L. I. Palladium Catalysed Alkoxycarbonylation of Phenols to Benzoate Esters. J. Chem. Soc., Chem. Commun. 1987, 904-905.
22. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Bis(tributyltin) Oxide. A Mild Neutral and Selective Reagent for Cleavage of Esters. Scope and Limitation of the Reaction. Tetrahedron Lett. 1991, 32, 4239-4242.
23. Brand, N.; Petkovich, M.; Krust, A.; Chambon, P.; de The, H.; Marchio, A.; Tiollais, P.; Dejean, A. Identification of A Second Human Retinoic Acid Receptor. Nature 1988, 332, 850-853.
24. Yang, N.; Schule, R.; Mangelsdorf, D. J.; Evans, R. M. Characterization of DNA Binding and Retinoic Acid Binding Properties of Retinoic Acid Receptor. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 3559-3663.
25. Dokoh, S.; Pike, J. W.; Chandler, J. S.; Mancini, J. M.; Haussler, M. R. An Improved Radioreceptor Assay for 1,25-Dihydroxyvitamin D in Human Plasma. Anal. Biochem. 1981, 116, 211-222.
26. Darmon, M.; Rocher, M.; Cavey, M.-T.; Martin, B.; Rabilloud, T.; Delescluse, C.; Shroot, B. Biological Activity of Retinoid Correlates With Affinity For Nuclear Receptors But Not For Cytosolic Binding Protein. Skin Pharmacol. 1988, 1, 161-175.
27. Chen, S.; Ostrowski, J.; Whiting, G.; Roalsvig, T.; Hammer, L.; Currier, S. J.; Honeyman, J.; Kwasniewski, B.; Yu, K.-L.; Sterzycki, R.; Kim, C. U.; Starrett, J. E., Jr.; Mansuri, M. M.; Reczek, P. R. Retinoic Acid Receptor Gamma Mediates Efficacy And Irritation In Animal Models. J. Invest. Dermatol. 1995, 104, 779-783.
28. Middleton, W. J. New Fluorinating Reagents. Dialkylaminosulfur Fluorides. J. Org. Chem. 1975, 40, 574-578.
29. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. Preparation of Trifluoromethyl And Other Perfluoroalkyl Compounds With (Perfluoroalkyl)trimethylsilanes. J. Org. Chem. 1991, 56, 984-989.
30. Shroot, B.; Eustache, J.; Bouclier, M. 2,6-Disubstituted Naphthalene Derivatives, A Process For Preparing The Same And Pharmaceutical And Cosmetic Compositions Containing The Same. U.S. Patent 4,581,380, 1986.
31. Vasios, G. W.; Gold, J. D.; Petkovich, M.; Chambon, P.; Gudas, L. J. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9099-9103.
32. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: A Laboratory Mannual; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1989.