Estrogen receptor ligands. Part 5: The SAR of dihydrobenzoxathiins containing modified basic side chains

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 14, 2004, Pages 3747-3751

  Tan, Qiang ^a   Birzin, Elizabeth T ^a   Chan, Wanda ^a   Yang, Yi Tien ^a   Pai, Lee Yuh ^a   Hayes, Edward C ^a   Dasilva, Carolyn A ^a   DiNinno, Frank ^a   Rohrer, Susan P ^a   Schaeffer, James M ^a   Hammond, Milton L ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Dihyrobenzoxathiin; Estrogen receptor; SERAM; SERM

Indexed keywords

BENZENE DERIVATIVE; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HYDROXYL GROUP; LEAD; LIGAND;

ARTICLE; CELL GROWTH; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; UTERUS GROWTH;

BINDING SITES; CELL LINE, TUMOR; ESTRADIOL ANTAGONISTS; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; LIGANDS; OXATHIINS; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

MINK CELL FOCUS-FORMING VIRUS;

EID: 2942625956     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.100     Document Type: Article

References (22)

1. Recent reviews on SERMs: Jordan V.C. J. Med. Chem. 46:2003;883
2. Jordan V.C. J. Med. Chem. 46:2003;1081
3. Meegan M.J., Lloyd D.G. Curr. Med. Chem. 10:2003;181
4. Miller C.P. Curr. Pharm. Des. 8:2002;2089
5. Bryant H.U. Endocr. Metabol. Disord. 3:2002;231
6. EVISTA: 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. J. Med. Chem. 41:1998;1272
7. NALVADEX: Jordan V.C. Br. J. Pharmacol. 110:1993;507
8. EM-652, SCH57068: Labrie M., Labrie C., Belanger A., Simard J., Giguere V., Tremblay A., Tremblay G. J. Steroid. Biochem. Mol. Biol. 79:2001;213
9. Lasofoxifene: Ke H.Z., Paralkar V.M., Grasser W.A., Crawford D.T., Qi H., Simmons H.A., Pirie C.M., Chidsey-Frink K.L., Owen T.A., Smock S.L., Chen H.K., Jee W.S.S., Cameron K.O., Rosati R.L., Brown T.A., DaSilva Jardine P., Thompson D.D. Endocrinology. 139:1998;2068
10. Bazedoxifene: 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.A., Lyttle C.R., Komm B.S. J. Med. Chem. 44:2001;1654
11. Kim S., Wu J.Y., Birzin E.T., Frisch K., Chan W., Pai L.-Y., Yang Y.T., Mosley R.T., Fitzgerald P.M.D., Sharma N., Dahllund J., Thorsell A.-G., DiNinno F., Rohrer S.P., Schaeffer J.M., Hammond M.L. J. Med. Chem. 47:2004;2171
12. Chen H.Y., Kim S., Wu J.Y., Birzin E.T., Chan W., Yang Y.T., DiNinno F., Rohrer S.P., Schaeffer J.M., Hammond M.L. Bioorg. Med. Chem. Lett. 14:2004;2551
13. DiNinno, F. P.; Chen, H. Y.; Kim, S.; Wu, J. Y. International Patent WO200232377
14. Kim S., Wu J.Y., Chen H.Y., Birzin E.T., Chan W., Yang Y.T., Colwell L., Li S., Dahllund J., DiNinno F., Rohrer S.P., Schaeffer J.M., Hammond M.L. Bioorg. Med. Chem. Lett. 14:2004;2741
15. The thiophenols 12 were prepared by known procedures with minor modifications: (a) Werner, G.; Biebrich, W. U. S. Patent 2,276,553; 2, 332, 418
16. Hanzlik R.P., Weller P.E., Desai J., Zheng J., Hall L.R., Slaughter D.E. J. Org. Chem. 55:1990;2736
17. Kim S., Wu J.Y., Chen H.Y., DiNinno F. Org. Lett. 5:2003;685
18. Zhu L., Wehmeyer R.M., Rieke R.D. J. Org. Chem. 56:1991;1445
19. Ganesh T., Kumar H., Krupadanam G.L. Synth. Commun. 29:1999;2069. and references cited therein
20. Wolfe J.P., Tomori H., Yin J., Sadighi J., Buchwald S.L. J. Org. Chem. 65:2000;1158
21. Compound 43 was prepared and the Stille coupling reaction was carried out according to general procedures in: Kiely J.S., Laborde E., Lesheski L.E., Bucsh R.A. J. Heterocycl. Chem. 28:1991;1581
22. Schmid C.R., Sluka J.P., Duke K.M., Glasebrook A.W. Bioorg. Med. Chem. Lett. 9:1999;523. and references cited therein