Estrogen receptor ligands. Part 15: Synthesis of benzothiopyran-based selective estrogen receptor alpha modulators (SERAM)

Heterocycles

Volumn 67, Issue 1, 2006, Pages 79-83

  Kim, Seongkon ^a   DiNinno, Frank ^a   Birzin, Elizabeth T ^b   Chan, Wanda ^b   Yang, Yi Tien ^b   Hammond, Milton L ^a  

^a Department of Medicinal Chemistry ^*  (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646859010     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(T)7     Document Type: Article

References (18)

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2. Kim S., Wu J.Y., Chen H.Y., and DiNinno F. Org. Lett. 5 (2003) 685
3. 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., and Hammond M.L. Bioorg. Med. Chem. Lett. 14 (2004) 2741
4. Chen H.Y., Kim S., Wu J.Y., Birzin E.T., Chan W., Yang Y.T., Dahllund J., DiNinno F., Rohrer S.P., Schaeffer J.M., and Hammond M.L. Bioorg. Med. Chem. Lett. 14 (2004) 2551
5. Song Z.J., King A.O., Waters M.S., Lang F., Zewge D., Bio M., Leazer Jr. J.L., Javadi G., Kassim A., Tschaen D.M., Reamer R.A., Rosner T., Chilenski J.R., Mathre D.J., Volante R.P., and Tillyer R. PNAS 101 (2004) 5776
6. Zhang Z., Chen Q., Li Y., Doss G., Dean B.J., Ngui J.S., Elipe M.S., Kim S., Wu J.Y., DiNinno F., Hammond M.L., Stearns R.A., Evans D.C., Baillie T.A., and Tang W. Chem. Res. Toxicol. 18 (2005) 675
7. Blizzard T.A., DiNinno F., Morgan II J.D., Chen H.Y., Wu J.Y., Gude C., Kim S., Chan W., Birzin E.T., Yang Y.T., Pai L.Y., Zhang Z., Hayes E.C., DaSilva C.A., Tang W., Rohrer S.P., Schaeffer J.M., and Hammond M.L. Bioorg. Med. Chem. Lett. 14 (2004) 3861
8. Blizzard T.A., DiNinno F., Morgan II J.D., Wu J.Y., Chen H.Y., Kim S., Chan W., Birzin E.T., Yang Y.T., Pai L.Y., Zhang Z., Hayes E.C., DaSilva C.A., Tang W., Rohrer S.P., Schaeffer J.M., and Hammond M.L. Bioorg. Med. Chem. Lett. 14 (2004) 3865
9. Blizzard T.A., DiNinno F., Morgan II J.D., Chen H.Y., Wu J.Y., Kim S., Chan W., Birzin E.T., Yang Y.T., Pai L.Y., Fitzgerald P.M.D., Sharma N., Li Y., Zhang Z., Hayes E.C., DaSilva C.A., Tang W., Rohrer S.P., Schaeffer J.M., and Hammond M.L. Bioorg. Med. Chem. Lett. 15 (2005) 107
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11. Hodgson H.H., and Jenkinson T.A. J. Chem. Soc. (1927) 1740
12. Meth-Cohn O., and Tarnowski B. Synthesis (1978) 56
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15. Ca. 3% yield of trans isomer was also formed. See also ref. 2.
16. D+227.6° (c 0.69, MeOH)
17. +)
18. Tan Q., Birzin E.T., Chan W., Yang Y.T., Pai L., Hayes E.C., DaSilva C.A., DiNinno F., Rohrer S.P., Schaeffer J.M., and Hammond M.L. Bioorg. Med. Chem. Lett. 14 (2004) 3753