Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling

ACS Combinatorial Science

Volumn 13, Issue 5, 2011, Pages 501-510

  Cho, Chul Hee ^a   Jung, Dai Il ^a,b   Neuenswander, Benjamin ^c   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

^b Dong A University   (South Korea)

^c UNIVERSITY OF KANSAS   (United States)

Author keywords

benzo b thiophene; desketoraloxifene; iodocyclization; palladium coupling; Parallel synthesis; selective estrogen receptor modulator (SERM)

Indexed keywords

PALLADIUM; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MOLECULAR LIBRARY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; THIOPHENES;

EID: 80052750698     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200090p     Document Type: Article

References (42)

1. Lerner, L. J.; Holthaus, F. J., Jr.; Thompson, C. R. A Nonsteroidal Estrogen Antagonist, 1-[ p -(2-Diethylaminoethoxy)phenyl]-1-phenyl-2-(p -methoxyphenyl)ethanol Endocrinology 1958, 63, 295-318
2. Weatherman, R. V.; Fletterick, R. J.; Scanlan, T. S. Nuclear-Receptor Ligands and Ligand-binding Domains Annu. Rev. Biochem. 1999, 68, 559-581 (Pubitemid 29449203)
3. Gustafsson, J. A. Therapeutic Potential of Selective Estrogen Receptor Modulators Curr. Opin. Chem. Biol. 1998, 2, 508-511
4. Harper, M. J.; Walpole, A. L. Contrasting Endocrine Activities of cis and trans Isomers in a Series of Substituted Triphenylethylenes Nature 1966, 212, 87
5. Jordan, V. C.; Phelps, E.; Lindgren, J. U. Effects of anti-Estrogens on Bone in Castrated and Intact Female Rats Breast Cancer Res. Tr. 1987, 10, 31-35 (Pubitemid 18038542)
6. Jordan, V. C. Tamoxifen: A Most Unlikely Pioneering Medicine Nat. Rev. Drug Discovery 2003, 2, 205-213 (Pubitemid 37361665)
7. Itami, K.; Kamei, T.; Yoshida, J. Diversity-Oriented Synthesis of Tamoxifen-Type Tetrasubstituted Olefins J. Am. Chem. Soc. 2003, 125, 14670-14671 (Pubitemid 37475535)
8. Killackey, M. A.; Hakes, T. B.; Pierce, V. K. Endometrial Adenocarcinoma in Breast Cancer Patients Receiving Antiestrogens Cancer Treat. Rep. 1985, 69, 237-238 (Pubitemid 15170469)
9. Lloyd, D. G.; Hughes, R. B.; Zisterer, D. M.; Williams, D. C.; Fattorusso, C.; Catalanotti, B.; Campiani, G.; Meegan, M. J. Benzoxepin-Derived Estrogen Receptor Modulators: A Novel Molecular Scaffold for the Estrogen Receptor J. Med. Chem. 2004, 47, 5612-5615 (Pubitemid 39447257)
10. Carta, G.; Knox, A. J. S.; Lloyd, D. G. Unbiasing Scoring Functions: A New Normalization and Rescoring Strategy J. Chem. Inf. Model. 2007, 47, 1564-1571 (Pubitemid 47210059)
11. Blizzard, T. A.; Morgan, J. D.; Mosley, R. T.; Birzin, E. T.; Frisch, K.; Rohrer, S. P.; Hammond, M. L. 2-Phenylspiroindenes: A Novel Class of Selective Estrogen Receptor Modulators (SERMs) Bioorg. Med. Chem. Lett. 2003, 13, 479-483 (Pubitemid 36259718)
12. Greenberger, L. M.; Annable, T.; Collins, K. I.; Komm, B. S.; Lyttle, C. R.; Miller, C. P.; Satyaswaroop, P. G.; Zhang, Y.; Frost, P. A New Antiestrogen, 2-(4-Hydroxy-phenyl)-3-methyl-1-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-1 H -indol-5-ol Hydrochloride (ERA-923), Inhibits the Growth of Tamoxifen-sensitive and -resistant Tumors and is Devoid of Uterotropic Effects in Mice and Rats Clin. Cancer Res. 2001, 7, 3166-3177 (Pubitemid 32963840)
13. Miller, C. P.; Collini, M. D.; Tran, B. D.; Harris, H. A.; Kharode, Y. P.; Marzolf, J. T.; Moran, R. A.; Henderson, R. A.; Bender, R. H. W.; Unwalla, R. J.; Greenberger, L. M.; Yardley, J. P.; Abou-Gharbia, M. A.; Lyttle, C. R.; Komm, B. S. Design, Synthesis, and Preclinical Characterization of Novel, Highly Selective Indole Estrogens J. Med. Chem. 2001, 44, 1654-1657 (Pubitemid 32852172)
14. Steinbaum, F. L.; De Jager, R.; Krakoff, I. Clinical Trial of Nafoxidine in Advanced Breast Cancer Med. Pediatr. Oncol. 1978, 4, 123-126 (Pubitemid 8345616)
15. Castaner, J.; Thorpe, P. Nafoxidine Drugs Future 1978, 3, 211-215 (Pubitemid 9015055)
16. Legha, S. S.; Slavik, M.; Carter, S. K. Nafoxidine-An Antiestrogen for the Treatment of Breast Cancer Cancer 1976, 38, 1535-1541
17. Laios, I.; Journe, F.; Laurent, G.; Nonclercq, D.; Toillon, R.-A.; Seo, H.-S.; Leclercq, G. Mechanisms Governing the Accumulation of Estrogen Receptor Alpha in MCF-7 Breast Cancer Cells Treated with Hydroxytamoxifen and Related Antiestrogens J. Steroid Biochem. Mol. Biol. 2004, 87, 207-221 (Pubitemid 37532528)
18. Neubauer, B. L.; McNulty, A. M.; Chedid, M.; Chen, K.; Goode, R. L.; Johnson, M. A.; Jones, C. D.; Krishnan, V.; Lynch, R.; Osborne, H. E.; Graff, J. R. The Selective Estrogen Receptor Modulator Trioxifene (LY133314) Inhibits Metastasis and Extends Survival in the PAIII Rat Prostatic Carcinoma Model Cancer Res. 2003, 63, 6056-6062 (Pubitemid 37187510)
19. Liu, H.; Liu, J.; van Breemen, R. B.; Thatcher, G. R. J.; Bolton, J. L. Bioactivation of the SERM Desmethylated Arzoxifene to Quinoids: 4′-Fluoro Substitution Prevents Quinoid Formation Chem. Res. Toxicol. 2005, 18, 162-173 (Pubitemid 40256234)
20. Delmas, P. D.; Bjarnason, N. H.; Mitlak, B. H.; Ravoux, A.-C.; Shah, A. S.; Huster, W. J.; Draper, M.; Christiansen, C. Effects of Raloxifene on Bone Mineral Density, Serum Cholesterol Concentrations, and Uterine Endometrium in Postmenopausal Women N. Engl. J. Med. 1997, 337, 1641-1647 (Pubitemid 27510100)
21. Weatherman, R. V.; Carroll, D. C.; Scanlan, T. S. Activity of a Tamoxifen-Raloxifene Hybrid Ligand for Estrogen Receptors at an AP-1 Site Bioorg. Med. Chem. Lett. 2001, 11, 3129-3131 (Pubitemid 33092008)
22. Suh, N.; Glasebrook, A. L.; Palkowitz, A. D.; Bryant, H. U.; Burris, L. L.; Starling, J. J.; Pearce, H. L.; Williams, C.; Peer, C.; Wang, Y.; Sporn, M. B. Arzoxifene, A New Selective Estrogen Receptor Modulator for Chemoprevention of Experimental Breast Cancer Cancer Res. 2001, 61, 8412-8415 (Pubitemid 33131117)
23. Qin, Z.; Kastrati, I.; Chandrasena, R. E. P.; Liu, H.; Yao, P.; Petukhov, P. A.; Bolton, J. L.; Thatcher, G. R. J. Design and Synthesis of Benzothiophene SERMs with Modulated Oxidative Activity and Receptor Affinity J. Med. Chem. 2007, 50, 2682-2692 (Pubitemid 46896076)
24. Grese, T. A.; Sluka, J. P.; Bryant, H. U.; Cullinan, G. J.; Glasebrook, A. L.; Jones, C. D.; Matsumoto, K.; Palkowitz, A. D.; Sato, M.; Termine, J. D.; Winter, M. A.; Yang, N. N.; Dodge, J. A. Molecular Determinants of Tissue Selectivity in Estrogen Receptor Modulators Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14105-14110 (Pubitemid 28009717)
25. Richardson, T. I.; Frank, S. A.; Wang, M.; Clarke, C. A.; Jones, S. A.; Ying, B.-P.; Kohlman, D. T.; Wallace, O. B.; Shepherd, T. A.; Dally, R. D.; Palkowitz, A. D.; Geiser, A. G.; Bryant, H. U.; Henck, J. W.; Cohen, I. R.; Rudmann, D. G.; McCann, D. J.; Coutant, D. E.; Oldham, S. W.; Hummel, C. W.; Fong, K. C.; Hinklin, R.; Lewis, G.; H., T.; D. J., A. Structure-Activity Relationships of SERMs Optimized for Uterine Antagonism and Ovarian Safety Bioorg. Med. Chem. Lett. 2007, 17, 3544-3549 (Pubitemid 46898811)
26. Palkowitz, A. D.; Glasebrook, A. L.; Thrasher, K. J.; Hauser, K. L.; Short, L. L.; Phillips, D. L.; Muehl, B. S.; Sato, M.; Shetler, P. K.; Cullinan, G. J.; Pell, T. R.; Bryant, H. U. Discovery and Synthesis of [6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(4-hydroxyphenyl)]benzo[ b ]thiophene: A Novel, Highly Potent, Selective Estrogen Receptor Modulator J. Med. Chem. 1997, 40, 1407-1416
27. Grese, T. A.; Cho, S.; Finley, D. A.; Godfrey, A. G.; Jones, C. D.; Lugar, C. W. I.; Martin, M. J.; Matsumoto, K.; Pennington, L. D.; Winter, M. A.; Adrian, M. D.; Cole, H. W.; Magee, D. E.; Phillips, D. L.; Rowley, E. R.; Short, L. L.; Glasebrook, A. L.; Bryant, H. U. Structure-Activity Relationships of Selective Estrogen Receptor Modulators: Modifications to the 2-Arylbenzothiophene Core of Raloxifene J. Med. Chem. 1997, 40, 146-167 (Pubitemid 27045072)
28. Yu, L.; Liu, H.; Li, W.; Zhang, F.; Luckie, C.; van Breemen, R. B.; Thatcher, G. R. J.; Bolton, J. L. Oxidation of Raloxifene to Quinoids: Potential Toxic Pathways via a Diquinone Methide and o -Quinones Chem. Res. Toxicol. 2004, 17, 879-888 (Pubitemid 38955346)
29. Grese, T. A.; Pennington, L. D.; Sluka, J. P.; Adrian, M. D.; Cole, H. W.; Fuson, T. R.; Magee, D. E.; Phillips, D. L.; Rowley, E. R.; Shetler, P. K.; Short, L. L.; Venugopalan, M.; Yang, N. N.; Sato, M.; Glasebrook, A. L.; Bryant, H. U. Synthesis and Pharmacology of Conformationally Restricted Raloxifene Analogues: Highly Potent Selective Estrogen Receptor Modulators J. Med. Chem. 1998, 41, 1272-1283 (Pubitemid 28208182)
30. Schmid, C. R.; Sluka, J. P.; Duke, K. M. Nucleophilic Aromatic Substitution on 3-Aroyl-2-arylbenzothiophenes. Rapid Access to Raloxifene and Other Selective Estrogen Receptor Modulators Tetrahedron Lett. 1999, 40, 675-678 (Pubitemid 29059431)
31. Macgregor, J. I.; Jordan, V. C. Basic Guide to the Mechanisms of Antiestrogen Action Pharmacol. Rev. 1998, 50, 151-196 (Pubitemid 28305723)
32. Bolton, J. L.; Yu, L.; Thatcher, G. R. J. Quinoids Formed from Estrogens and Antiestrogens Methods Enzymol. 2004, 378, 110-123
33. Bianchini, C.; Meli, A. Thiophene, Benzo[ b ]thiophene and Dibenzo[ b, d ]thiophene as Precursors to Highly Conjugated Organosulfur Compounds Synlett 1997, 643-649 (Pubitemid 127495079)
34. Irie, M.; Uchida, K. Synthesis and Properties of Photochromic Diarylethenes with Heterocyclic Aryl Groups Bull. Chem. Soc. Jpn. 1998, 71, 985-996 (Pubitemid 128499866)
35. Zhang, T. Y.; O'Toole, J.; Proctor, C. S. Recent Advances in the Synthesis and Applications of Benzo[ b ]thiophenes Sulfur Rep. 1999, 22, 1-47
36. Pelkey, E. T. Five-Membered Ring Systems: Thiophenes & Se, Te Analogs Prog. Heterocycl. Chem. 2003, 15, 116-139
37. Yue, D.; Larock, R. C. Synthesis of 2,3-Disubstituted Benzo[ b ]thiophenes via Palladium-Catalyzed Coupling and Electrophilic Cyclization of Terminal Acetylenes J. Org. Chem. 2002, 67, 1905-1909 (Pubitemid 34246585)
38. Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. Solution-Phase Parallel Synthesis of a Multi-substituted Benzo[ b ]thiophene Library J. Comb. Chem. 2009, 11, 900-906
39. Cho, C.-H.; Neuenswander, B.; Larock, R. C. Diverse Methyl Sulfone-Containing Benzo[ b ]thiophene Library via Iodocyclization and Palladium-Catalyzed Coupling J. Comb. Chem. 2010, 12, 278-285
40. Cho, C.-H.; Jung, D.-I.; Larock, R. C. A New Approach to Desketoraloxifene Analogs from Oxygen-Bearing 3-Iodobenzo[ b ]thiophenes Prepared via Iodocyclization Tetrahedron Lett. 2010, 51, 6485-6488
41. Mehta, S.; Waldo, J. P.; Larock, R. C. Competition Studies in Alkyne Electrophilic Cyclization Reactions J. Org. Chem. 2009, 74, 1141-1147
42. Mitsunobu, O.; Yamada, Y. Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382