Design and synthesis of tamoxifen derivatives as a selective estrogen receptor down-regulator

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 1, 2014, Pages 87-89

  Shoda, Takuji ^a   Okuhira, Keiichiro ^a   Kato, Masashi ^a,b   Demizu, Yosuke ^a   Inoue, Hideshi ^b   Naito, Mikihiko ^a   Kurihara, Masaaki ^a,c  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Breast cancer; Estrogen receptor; SERD; Tamoxifen

Indexed keywords

4 (1,2 DIPHENYL 1 BUTENYL)CINNAMIC ACID; ESTROGEN RECEPTOR; FULVESTRANT; TAMOXIFEN DERIVATIVE; BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL;

ARTICLE; CELL STRAIN MCF 7; DRUG DESIGN; DRUG EFFECT; DRUG EFFICACY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; BREAST CANCER; CANCER CHEMOTHERAPY; CANCER INHIBITION; CANCER RISK; DOWN REGULATION; DRUG BIOAVAILABILITY; ENDOMETRIUM CANCER; ENZYME METABOLISM; GENE EXPRESSION; HUMAN; HUMAN CELL; LIGAND BINDING; PROTEIN DEGRADATION; REAL TIME POLYMERASE CHAIN REACTION; TARGET ORGAN; UTERUS CANCER;

BREAST CANCER; ESTROGEN RECEPTOR; SERD; TAMOXIFEN;

DOSE-RESPONSE RELATIONSHIP, DRUG; DOWN-REGULATION; DRUG DESIGN; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; TAMOXIFEN;

EID: 84891484542     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.11.078     Document Type: Article

References (30)

1. F. Holst, P.R. Stahl, C. Ruiz, O. Hellwinkel, Z. Jehan, M. Wendland, A. Lebeau, L. Terracciano, K. Al-Kuraya, F. Janicke, G. Sauter, and R. Simon Nat. Genet. 39 2007 655
2. S.F. Doisneau-Sixou, C.M. Sergio, J.S. Carroll, R. Hui, E.A. Musgrove, and R.L. Sutherland Endocr. Relat. Cancer 10 2003 179
3. J.S. Foster, D.C. Henley, S. Ahamed, and J. Wimalasena Trends Endocrinol. Metab. 12 2001 320
4. J.S. Foster, D.C. Henley, A. Bukovsky, P. Seth, and J. Wimalasena Mol. Cell. Biol. 21 2001 794
5. B.J. Deroo, and K.S. Korach J. Clin. Invest. 116 2006 561
6. Early Breast Cancer Trialists' Collaborative Group, Lancet 1998, 351, 1451.
7. R.P. Kedar, T.H. Bourne, T.J. Powles, W.P. Collins, S.E. Ashley, D.O. Cosgrove, and S. Campbell Lancet 343 1994 1318
8. L. Bernstein, D. Deapen, J.R. Cerhan, S.M. Schwartz, J. Liff, E. McGann-Maloney, J.A. Perlman, and L. Ford J. Natl. Cancer Inst. 91 1999 1654
9. Y. Shang, and M. Brown Science 295 2002 2465
10. S.J. Howell, S.R. Johnston, and A. Howell Best Pract. Res. Clin. Endocrinol. Metab. 18 2004 47
11. C.K. Baumann, and M. Castiglione-Gertsch Drugs 67 2007 2335
12. A.U. Buzdar, and J.F. Robertson Ann. Pharmacother. 40 2006 1572
13. P.F. Bross, A. Baird, G. Chen, J.M. Jee, R.T. Lostritto, D.E. Morse, L.A. Rosario, G.M. Williams, P. Yang, A. Rahman, G. Williams, and R. Pazdur Clin. Cancer Res. 9 2003 4309
14. A. Howell, and P. Abram Cancer Treat Rev 31 2005 S3
15. J.F. Robertson, A. Howell, V.A. Gorbunova, T. Watanabe, T. Pienkowski, and M.R. Lichinitser Breast Cancer Res. Treat. 92 2005 169
16. E.J. Brazier, P.J. Hogan, C.W. Leung, A. OKarney-McMullan, A.K. Norton, L. Powell, L. Robinson, G.E. Powell, and E.G. Williams Org. Process Res. Dev. 14 2010 544
17. T.M. Willson, B.R. Henke, T.M. Momtahen, P.S. Charifson, K.W. Batchelor, D.B. Lubahn, L.B. Moore, B.B. Oliver, H.R. Sauls, and J.A. Triantafillou et al. J. Med. Chem. 37 1994 1550
18. A.L. Wijayaratne, S.C. Nagel, L.A. Paige, D.J. Christensen, J.D. Norris, D.M. Fowlkes, and D.P. McDonnell Endocrinology 140 1999 5828
19. C.E. Connor, J.D. Norris, G. Broadwater, T.M. Willson, M.M. Gottardis, M.W. Dewhirst, and D.P. McDonnell Cancer Res. 61 2001 2917
20. A.C. Pike, A.M. Brzozowski, J. Walton, R.E. Hubbard, A.G. Thorsell, Y.L. Li, J.A. Gustafsson, and M. Carlquist Structure 9 2001 145
21. A.K. Shiau, D. Barstad, P.M. Loria, L. Cheng, P.J. Kushner, D.A. Agard, and G.L. Greene Cell 95 1998 927
22. Y. Demizu, K. Okuhira, H. Motoi, A. Ohno, T. Shoda, K. Fukuhara, H. Okuda, M. Naito, and M. Kurihara Bioorg. Med. Chem. Lett. 22 2012 1793
23. H. Brauch, and V.C. Jordan Eur. J. Cancer 45 2009 2274
24. W.A. Teft, S.E. Mansell, and R.B. Kim Drug Metab. Dispos. 39 2011 558
25. Z. Desta, B.A. Ward, N.V. Soukhova, and D.A. Flockhart J. Pharmacol. Exp. Ther. 310 2004 1062
26. M.D. Johnson, H. Zuo, K.-H. Lee, J.P. Trebley, J.M. Rae, R.V. Weatherman, Z. Desta, D.A. Flockhart, and T.C. Skaar Breast Cancer Res. Treat. 85 2004 151
27. S.M. Ali, A. Ahmad, S. Shahabuddin, M.U. Ahmad, S. Sheikh, and I. Ahmad Bioorg. Med. Chem. Lett. 20 2010 2665
28. I. Laios, F. Journe, G. Laurent, D. Nonclercq, R.-A. Toillon, H.-S. Seo, and G. Leclercq J. Steroid Biochem. Mol. Biol. 87 2003 207
29. J.S. Lewis-Wambi, H. Kim, R. Curpan, R. Grigg, M.A. Sarker, and V.C. Jordan Mol. Pharmacol. 80 2011 610
30. K. Okuhira, Y. Demizu, T. Hattori, N. Ohoka, N. Shibata, T. Nishimaki-Mogami, H. Okuda, M. Kurihara, and M. Naito Cancer Sci. 104 2013 1492