A novel and stereoselective synthesis of 7α-alkynylestra-1,3,5(10)-triene-3,17β-estradiol

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5723-5726

  Ahmed, Naseem ^a   van Lier, Johan E ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

7 Ethenyl 3,17 estradiol and its 17 acetate derivative; Chemical synthesis; Conjugate addition; Estrogen receptor antagonist

Indexed keywords

7ALPHA ETHENYLESTRA 1,3,5(10) TRIENE 3,17BETA ESTRADIOL; 7ALPHA ETHENYLESTRA 1,3,5(10) TRIENE 3,17BETA ESTRADIOL ACETATE; ACETIC ACID DERIVATIVE; ALDEHYDE; ALKYNYL GROUP; ESTRADIOL DERIVATIVE; LIGAND; NANDROLONE; PALLADIUM; RECEPTOR BLOCKING AGENT; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; CYANATION; IMAGING; LIGAND BINDING; METHYLATION; QUANTUM YIELD; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOCHEMISTRY; STEROIDOGENESIS;

EID: 34447542515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.098     Document Type: Article

References (56)

1. Paulmurugan R., and Gambhir S.S. PNAS 103 (2006) 15883
2. Lippman M.E., and Allegra J.C. New Engl. J. Med. 299 (1978) 930
3. Fisher B., Osborne C.K., Margolese R., and Bloomer W. Cancer Medicine. 4th ed. Vol. 1 (1997), Williams & Wilkins, Baltimore p 2349
4. Jordan V.C., and Brodie A.M.H. Steroids 72 (2007) 7
5. MacGregor J.I., and Jordan V.C. Pharmacol. Rev. 50 (1998) 151
6. Top S., El-Hafa H., Vessieres A., Quivy J., Vassermann J., Hughes D.W., McGlinchey M.J., Mornon J.-P., Thoreau E., and Jaouen G. J. Am. Chem. Soc. 117 (1995) 8373
7. Osborne C.K., Wakeling A., and Nicholson R.I. Br. J. Cancer 90 (2004) S2-S6
8. Bowler J., Lilley T.J., Pittam J.D., and Wakeling A.E. Steroids 54 (1989) 71
9. Thompson M.J., Hutchinson E.J., Stratford T.H., Bowler W.B., and Blackburn G.M. Tetrahedron Lett. 45 (2004) 1207
10. Jones S.E. Semin. Oncol. 30 (2003) 14
11. Adamczyk M., Johnson D., and Reddy E.A. Steroids 62 (1997) 771
12. Hussey S.L., He E., and Peterson B.R. Org. Lett. 4 (2002) 415
13. Skaddan M.B., Wust F.R., and Katzenellenbogen J.A. J. Org. Chem. 64 (1999) 8108
14. Mitra K., Marquis J.C., Hillier S.M., Rye P.T., Zayas B., Lee A.S., et al. J. Am. Chem. Soc. 124 (2002) 1862
15. Hussey S.L., Muddana S.S., and Peterson B.R. J. Am. Chem. Soc. 125 (2003) 3692
16. Osborne C.K., and Schiff R. J. Clin. Oncol. 23 (2005) 1616
17. Beauregard J., Turcotte E., and Benard F. PET Clin. 1 (2006) 51
18. Mankoff D.A., Tewson T.J., and Eary J.F. Nucl. Med. Biol. 24 (1997) 341
19. Gosling J.P. Clin. Chem. 36 (1990) 1408
20. Wild D. The lmmunoassay Handbook (1994), Stockton Press, New York p 366
21. Martynow J., Krupa M., Les A., Kutner A., and Szelejewski W. Org. Process Res. Dev. 8 (2004) 846
22. Bucourt R., Vignau M., Torelli V., Richard-Foy H., Geynet C., Secco-Millet C., Redeuilh G., and Baulieu E.E. J. Biol. Chem. 253 (1978) 8221
23. Muhelenbruch B., Kirmeier F., and Roth H.J. Arch. Pharm. (Weinheim) 319 (1986) 177
24. Bowler J., Lilley T.J., Pittam J.D., and Wakeling A.E. Steroids 54 (1989) 71
25. Levesque C., and Merand Y. Steroids 54 (1989) 71
26. Levesque C., Merand Y., Dufour J.-M., Labrie C., and Labrie F. J. Med. Chem. 34 (1991) 1624
27. Hauptmann H., Paulus B., Kaiser T., and Luppa T.B. Bioconjugate Chem. 11 (2000) 537
28. French A.N., Wilson S.R., Welch M.J., and Katzenellenbogen J.A. Steroids 58 (1993) 157
29. Kunzer H., Thiel M., Sauer G., and Wiechert R. Tetrahedron Lett. 35 (1994) 1691
30. Kunzer H., Thiel M., and Peschke B. Tetrahedron Lett. 37 (1996) 1771
31. Spera D., Cabrera G., Fiaschi R., Carlson K.E., Katzenellenbogen J.A., and Napolitano E. Bioorg. Med. Chem. 12 (2004) 4393
32. Luyt L.G., Bigott H.M., Welch M.J., and Katzenellenbogen J.A. Bioorg. Med. Chem. 11 (2003) 4977
33. VanBrocklin H.F., Liu A., Welch M.J., O'Neil J.P., and Katzenellenbogen J.A. Steroids 59 (1994) 34
34. Morais G.R., Oliveira M.C.D.N., and Thiemann T. Lett. Org. Chem. 3 (2006) 214
35. Blazejewski J.C., Wilmshurst M.P., Popkin M.D., Wakselman C., Nonclercq G.D., Ma Y., Seoc H.S., and Leclercq G. Bioorg. Med. Chem. 11 (2003) 335
36. Neeman M., and Osawa Y. Tetrahedron Lett. 4 (1963) 1987
37. Wintersteiner O., Moore M., and Cohen A.I. J. Org. Chem. 29 (1964) 1325
38. Thiemann T., Umeno K., Imai M., Shima Y., and Mataka S. J. Chem. Res. (S) (2002) 1
39. Lovely C.J., Gilbert N.E., Liberto M.M., Sharp D.W., Lin Y.C., and Brueggemeier R.W. J. Med. Chem. 39 (1996) 1917
40. Labaree D.C., Zhang J.-X., Harris H.A., O'Connor C., Reynolds T.Y., and Hochberg R.B. J. Med. Chem. 46 (2003) 1886
41. van der Louw, J.; Leysen, D.; Bursi, R. B. U.S. Patent 6,756,366,B1, 2004.
42. Jiang X.-R., Sowell J.W., and Zhu B.T. Steroids 71 (2006) 334
43. Ahmed N., Dubuc C., Rousseau J., Benard F., and van Lier J.E. Bioorg. Med. Chem. Lett. 17 (2007) 3212
44. Ali H., Rousseau J., Ahmed N., Guertin V., Hochberg R.B., and van Lier J.E. Steroids 68 (2003) 1163
45. Ali H., and van Lier J.E. Bioorg. Med. Chem. Lett. 12 (2002) 2847
46. Ali H., Rousseau J., Paquette B., Dubé C., Marko B., and van Lier J.E. Steroids 68 (2003) 1189
47. Seimbille Y., Benard F., and van Lier J.E. J. Chem. Soc. Perkin Trans. 1 (2002) 2275
48. DaSilva J.N., and van Lier J.E. J. Med. Chem. 33 (1990) 430
49. Ali H., Rousseau J., and van Lier J.E. J. Med. Chem. 36 (1993) 264
50. Nickisch K., Bittler D., Laurent H., Losert W., Nishino Y., Schillinger E., and Wiechert R. J. Med. Chem. 33 (1990) 509
51. Labaree D.C., Zhang J.-X., Harris H.A., O'Connor C., Reynolds T.Y., and Hochberg R.B. J. Med. Chem. 46 (2003) 1886
52. Rao P.N., Cessac J.W., and Kim H.K. Steroids 59 (1994) 621
53. Geis O., and Schmalz H.-G. Angew. Chem., Int. Ed. 37 (1998) 911
54. Seyferth D., Nestle M.O., and Wehman A.T. J. Am. Chem. Soc. 97 (1975) 7417
55. Watanabe M., Mataka S., and Thies Thiemann T. Steroids 70 (2005) 856
56. +) 296.1776, found 296.1782.