Synthesis of novel nitro-substituted triaryl pyrazole derivatives as potential estrogen receptor ligands

Molecules

Volumn 12, Issue 7, 2007, Pages 1259-1273

  Naoum, Fotini ^a   Kasiotis, Konstantinos M ^a   Magiatis, Prokopios ^a,b   Haroutounian, Serkos A ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Estrogen receptor binding affinity; Pyrazoles; SERMs

Indexed keywords

ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; LIGAND; NITRO DERIVATIVE; PYRAZOLE; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; HUMAN; METABOLISM; SYNTHESIS;

ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; LIGANDS; NITRO COMPOUNDS; PYRAZOLES;

EID: 34547674570     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12071259     Document Type: Article

References (27)

1. (a) Veeneman, G. H. Non-Steroidal Subtype Selective Estrogens. Curr. Med. Chem. 2005, 12, 1077-1136;
2. (b) Ghosh, U.; Ganessunker, D.; Sattigeri, V. J.; Carlson, K. E.; Mortensen, D. J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Estrogenic diazenes: heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes. Bioorg. Med. Chem. 2003, 11, 629-657;
3. (c) Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Comparative QSAR Analysis of Estrogen Receptor Ligands. Chem. Rev. 1999, 99, 723-744.
4. Compton, D. R.; Sheng, S. B.; Carlson, K. E.; Rebacz, N. A.; Lee, I. Y.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Pyrazolo[1,5-a] pyrimidines: Estrogen Receptor Ligands Possessing Estrogen Receptor ? Antagonist Activity. J. Med. Chem. 2004, 47, 5872-5893.
5. Compton, D. R.; Carlson, K. E.; Katzenellenbogen, J. A. Pyrazolo[1,5-a]pyrimidines as estrogen receptor ligands: defining the orientation of a novel heterocyclic core. Bioorg. Med. Chem. Lett. 2004, 14, 5681-5684.
6. Magarian, R. A.; Overaacre, L. B.; Singh, S.; Meyer, K. L. Medicinal Chemistry of Nonsteroidal Antiestrogens: A Review. Curr. Med. Chem. 1994, 1, 61-104.
7. (a) Hartman, J.; Lindberg, K.; Morani, A.; Inzunza, J.; Ström, A.; Gustafsson, J.-Å. Estrogen Receptor β Inhibits Angiogenesis and Growth of T47D Breast Cancer Xenografts. Cancer Res. 2006, 66, 11207-11213;
8. (b) Gustafsson, J.-Å. ER beta scientific visions translate to clinical uses. Climacteric 2006, 9, 156-160.
9. Hillisch, A.; Peters, O.; Kosemund, D.; Müller, G.; Walter, A.; Schneider, B.; Reddersen, G.; Elger, W.; Fritzmeier, K.-H. Dissecting Physiological Roles of Estrogen Receptor α and β with Potent Selective Ligands from Structure-Based Design. Mol. Endocrinol. 2004, 18, 1599-1609.
10. (a) Pettersson, K.; Gustafsson, J.-Å. Role of Estrogen Receptor Beta in Estrogen Action. Ann. Rev. Physiol. 2001, 63, 165-192;
11. (b) Nilsson, S. Kuiper, G. G. J. M.. Gustafsson, J.-Å. ERβ: a novel estrogen receptor offers the potential for new drug development. Trends Endocrinol. Metab. 1998, 9, 387-395;
12. (c) Kuiper, G. G. J. M.; Enmark, E.; Pelto-Huikko, M.; Nilsson, S.; Gustafsson, J.-Å. Cloning of a novel estrogen receptor expressed in rat prostate and ovary. Proc. Natl. Acad. Sci. U.S.A 1996, 93, 5925-5930.
13. Stauffer, S. R.; Coletta, C. J.; Tedesco, R.; Nishigushi, G.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Pyrazole Ligands: Structure-Affinity/Activity Relationships and Estrogen Receptor-α- Selective Agonists. J. Med. Chem. 2000, 43, 4934-4947.
14. Fink, B. E.; Mortensen, D. S.; Stauffer, S. R.; Aron, Z. D.; Katzenellenbogen, J. A. Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens. Chem. Biol. 1999, 6, 205-219.
15. Stauffer, S. R.; Huang, Y. R.; Aron, Z. D.; Coletta, C. J.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen. J. A. Triarylpyrazoles with basic side chains development of pyrazole-based estrogen receptor antagonists. Bioorg. Med. Chem. 2001, 9, 151-161.
16. Lin, X.; Huebner, V. Non-steroidal ligands for steroid hormone receptors. Curr. Opin. Drug Disc. 2000, 3, 383-398.
17. Pezzella, A.; Manini, P.; Napolitano, A.; Crescenzi, O.; Barone, V.; d'Ischia, M. Steroids. Oxidative chemistry of 2-nitro and 4-nitroestradiol: Dichotomous behavior of radical intermediates and novel potential routes for oxyfunctionalization and B-ring fission of steroidal scaffolds. Steroids 2005, 70, 543-550.
18. Dubs, M.; Dieks, H.; Günther, W.; Kötteritzsch, M.; Poppitz, W.; Schönecker, B. O-Silylated steroidal cis-aminoalcohols as chiral auxiliaries: highly diastereoselective Pd-catalyzed cyclopropanation of α,β-unsaturated aldimines. Tetrahedron Lett. 2002, 43, 2499-2503.
19. Davis, A. P.; Joos, J. B. Steroids as organising elements in anion receptors. Coord. Chem. Rev. 2003, 240, 143-156.
20. Mueck, A. O.; Seeger, H. Hormone Therapy after Endometrial Cancer. Horm. Res. 2004, 62, 40-48.
21. Beauregard, J.-M.; Turcotte, E.; Bénard, F. Steroid receptor imaging in breast cancer. PET Clin. North Amer. 2006, 1, 51-70.
22. Brandenburger, F.; Matthes, B.; Seifert, K.; Strohriegl, P. Cholesteric polymeric networks with steroids as chiral components. Liq. Crystal. 2001, 28, 1035-1039.
23. Santaniello, E.; Ravasi, M.; Ferraboschi, P. A-Ring nitration of estrone. J. Org. Chem. 1983, 48, 739-740.
24. Toader, V.; Xu, X.; Nicolescu, A.; Yu, L.; Bolton, J.; Thatcher, G. R. Nitrosation, Nitration, and Autoxidation of the Selective Estrogen Receptor Modulator Raloxifene by Nitric Oxide, Peroxynitrite, and Reactive Nitrogen/Oxygen Species. Chem. Res. Toxicol. 2003, 16, 1264-1276.
25. Palomino, E.; Heeg, M. J.; Pilat, M. J.; Hafner, M.; Polin, L.; Brooks, S. C. Crystal structure, receptor binding, and gene regulation of 2- and 4-nitroestradiols. Steroids 1996, 61, 670-676.
26. Alberola, A.; Andres, C.; Gonzalez Ortega, A.; Pedrosa, R. Regiospecific synthesis of 1-arylpyrazoles. J. Heterocycl. Chem. 1984, 21, 1575-1576.
27. Fokialakis, N.; Lambrinidis, G.; Mitsiou, D. J.; Aligiannis, N.; Mitakou, S.; Skaltsounis, A. L.; Pratsinis, H.; Mikros, E.; Alexis, M. N. A New Class of Phytoestrogens: Evaluation of the Estrogenic Activity of Deoxybenzoins. Chem. Biol. 2004, 11, 397-406.