Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4- hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 18, 2012, Pages 5999-6003

  Haddad, Terra ^a   Gershman, Rachel ^a   Dilis, Robert ^a   Labaree, David ^b   Hochberg, Richard B ^b   Hanson, Robert N ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Conformations; Estrogen receptors; Isoxazoles; Receptor binding; Suzuki coupling reaction; Synthesis

Indexed keywords

4 ALKYLVINYL 3,5 BIS(4 HYDROXYPHENYL)ISOXAZOLE; 4 STYRYL 3,5 BIS(4 HYDROXYPHENYL)ISOXAZOLE; BORONIC ACID DERIVATIVE; ESTROGEN RECEPTOR ALPHA; ISOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING ASSAY; CROSS COUPLING REACTION; DEMETHYLATION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; PROTEIN DOMAIN; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION;

DOSE-RESPONSE RELATIONSHIP, DRUG; ESTROGEN RECEPTOR ALPHA; ISOXAZOLES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84865502561     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.06.097     Document Type: Article

References (27)

1. H. Gao, J.A. Katzenellenbogen, R. Garg, and C. Hansch Chem. Rev. 99 1999 723
2. U. Ghosh, D. Ganessunker, V.J. Sattigeri, K.E. Carlson, D.S. Mortensen, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Bioorg. Med. Chem. Lett. 11 2003 629
3. D.S. Mortensen, A.L. Rodriguez, K.E. Carlson, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 44 2001 3838
4. D.S. Mortensen, A.L. Rodriguez, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Bioorg. Med. Chem. Lett. 11 2001 2521
5. S.R. Stauffer, C.J. Coletta, R. Tedesco, G. Nishiguchi, K.E. Carlson, J. Sun, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 43 2000 4934
6. G.A. Nishiguchi, A.L. Rodriguez, and J.A. Katzenellenbogen Bioorg. Med. Chem. Lett. 12 2002 947
7. Y.R. Huang, and J.A. Katzenellenbogen Org. Lett. 2 2000 2833
8. S.R. Stauffer, and J. Katzenellenbogen Comb. Chem. 2 2000 318
9. Katzenellenbogen, J. A.; Katzenellenbogen, B. S.; Fink, B. E.; Stauffer, S. R.; Mortensen, D. S.; Sattigeri, V. J.; Huang, Y. WO 2000019994 A1, 2000.
10. B.E. Fink, D.E. Mortensen, S.R. Stauffer, Z.D. Aron, and J.A. Katzenellenbogen Chem. Biol. 6 1999 205
11. S.R. Stauffer, Y. Huang, C.J. Coletta, R. Tedesco, and J.A. Katzenellenbogen Bioorg. Med. Chem. 9 2001 141
12. R. Gust, R. Keilitz, K. Schmidt, and M. von Rauch Arch. Pharm. 335 2002 463
13. R. Gust, S. Busch, R. Keilitz, K. Schmidt, and M. von Rauch Arch. Pharm. 336 2003 456
14. A. Schaefer, A. Wellner, M. Strauss, G. Wolber, and R. Gust ChemMedChem 6 2011 2055
15. A. Schaefer, A. Wellner, and R. Gust ChemMedChem 6 2011 794
16. J. Zimmermann, R. Liebl, and E. von Angerer Steroid Biochem. Molec. Biol. 94 2005 57
17. J. Zimmermann, and E. Von Angerer J. Steroid Biochem. Mol. Biol. 96 2007 259
18. Huebner, V. D.; Lin, X.; James, I.; Chen, L.; Desai, M.; Moore, J. C.; Krywult, B.; Navaratnam, T.; Singh, R.; Trainor, R.; Wang, L. WO 0008001 A1, 200002017.
19. M. Schnurch, R. Flasik, A.F. Khan, M. Spina, M.D. Mihovilovic, and P. Stanetty Eur. J. Org. Chem. 2006 3283
20. R. Chinchilla, and C. Najera Chem. Soc. Rev. 40 2011 5084
21. Q.I. Churches, H.E. Stewart, S.B. Cohen, A. Shroder, P. Turner, and C.A. Hutton Pure Appl. Chem. 80 2008 687
22. A. Minkkila, S.M. Saario, H. Kasnanen, J. Leppanen, A. Poso, and T. Nevalainen J. Med. Chem. 51 2008 7057
23. C. Peng, W. Zhang, G. Yan, and J. Wang Org. Lett. 11 2009 1667
24. P. Angibaud, K. Van Emelen, L. Decrane, S. van Brandt, P. ten Holte, I. Pilatte, B. Roux, V. Poncelet, D. Speybrouck, L. Queguiner, S. Gaurrand, A. Marien, W. Floren, L. Janssen, M. Verdonck, J. van Dun, J. van Gompel, R. Gilissen, C. Mackie, M. Du Jardin, J. Peeters, M. Noppe, L. Van Hijfte, E. Freyne, M. Page, M. Janicot, and J. Arts Bioorg. Med. Chem. Lett. 20 2010 294
25. D.C. Labaree, J. Shang, H.A. Harris, C. O'Connor, T.Y. Reynolds, and R.B. Hochberg J. Med. Chem. 2003 1886 46
26. S. Green, P. Walter, V. Kumar, A. Krust, J.M. Bonert, P. Argos, and P. Chambon Nature 320 1986 134
27. Insight II, 97.2/ Discover 2.9.7 (MSI Inc. San Diego) 1997.