Neighboring group participation: Part 16. Stereoselective synthesis and receptor-binding examination of the four stereoisomers of 16-bromomethyl-3,17- estradiols

Steroids

Volumn 71, Issue 2, 2006, Pages 141-153

  Szájli, Ágota ^a   Wölfling, János ^a   Mernyák, Erzsébet ^a   Minorics, Renáta ^a   Márki, Árpád ^a   Falkay, George ^a   Schneider, Gyula ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

16 Bromomethylestra 1,3,5(10) triene 3,17 diol isomers; Androgen; Debenzylation; Estrogen; Front side neighboring group participation; Progesterone receptor binding; Wagner Meerwein rearrangement

Indexed keywords

16 BROMOMETHYL 3,17 ESTRADIOL DERIVATIVE; ACETIC ACID; ACETIC ANHYDRIDE; ESTRADIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; RADIOASSAY; RECEPTOR BINDING; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANIMALS; BINDING, COMPETITIVE; DIHYDROTESTOSTERONE; ESTRADIOL; ESTRADIOL ANTAGONISTS; FEMALE; MALE; MOLECULAR CONFORMATION; PREGNENEDIONES; PROSTATE; RADIOLIGAND ASSAY; RATS; RECEPTORS, ANDROGEN; RECEPTORS, ESTROGEN; RECEPTORS, PROGESTERONE; STEREOISOMERISM; UTERUS;

EID: 30644467736     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.09.008     Document Type: Article

References (25)

1. J. Wölfling, L. Hackler, E. Mernyák, Gy. Schneider, I. Tóth, and M. Szécsi Neighboring group participation. Part 15. Stereoselective synthesis of some steroidal tetrahydrooxazin-2-ones, as novel presumed inhibitors of human 5α-reductase Steroids 69 2004 451 460
2. E.E. Baulieu Hormones, a complex communications network E.E. Baulieu P.A. Kelly Hormones 1990 Hermann Publishers/Chapman and Hall Paris/New York 147
3. T. Nakata, S. Takashima, Y. Shiotsu, C. Murakata, H. Ishida, and S. Akinaga Role of steroid sulfatase in local formation of estrogen in post-menopausal breast cancer patients J Steroid Biochem Mol Biol 86 2003 455 460
4. C. Lévesque, Y. Mérand, J.M. Dufour, C. Labrie, and F. Labrie Synthesis and biological activity of new halo-steroidal antiestrogens J Med Chem 34 1991 1624 1630
5. 18F]fluoro)estrogens: systematic investigation of a new series of fluorine-18-labeled estrogens as potential imaging agents for estrogen-receptor-positive breast tumors J Med Chem 36 1993 1619 1629
6. 125I]iodoestradiol derivatives: synthesis and effect on estrogen receptor binding and receptor-mediated target tissue uptake J Med Chem 36 1993 4255 4263
7. J. Wölfling, É. Frank, E. Mernyák, G. Bunkóczi, J.A. Cvesta Seijo, and Gy. Schneider Synthesis of novel halogen-containing d-homoestrone and 13α-d-homoestrone derivatives by Lewis acid-induced intramolecular Prins reaction Tetrahedron 58 2002 6851 6861
8. M. Dumont, V. Luu-The, Y. de Launoit, and F. Labrie Expression of human 17β-hydroxysteroid dehydrogenase in mammalian cells J Steroid Biochem Mol Biol 41 1992 605 608
9. C. Trudel, J. Couët, V. Luu-The, J. Simard, and F. Labrie Distribution of 17β-hydroxysteroid dehydrogenase gene expression and activity in rat and human tissues J Steroid Biochem Mol Biol 41 1992 592 603
10. K.-M. Sam, R. Boivin, J. Côte, N. Naimi, and D. Poirier Développement d'inhibiteurs de la 17β-hydroxystéroide déshidrogénase Med Sci 8 Suppl. 2 1992 47
11. J.D. Pelletier, F. Labrie, and D. Poirier N-Butyl,N-methyl,11-[3′, 17′β-(dihydroxy)-1′,3′,5′(10)-estratrien- 16′α-yl]-9(R/S)-bromo undecanamide: synthesis, and 17β-HSD inhibiting, estrogenic, and antiestrogenic activities Steroids 59 1994 536 547
12. D.F. Heiman, S.G. Senderoff, J.A. Katzenellenbogen, and R.J. Neeley Estrogen receptor-based imaging agents. 1. Synthesis and receptor binding affinity of some aromatic and D-ring halogenated estrogens J Med Chem 23 1980 994 1002
13. T.L. Fevig, M.K. Mao, and J.A. Katzenellenbogen Estrogen receptor binding tolerance of 16α-substituted estradiol derivatives Steroids 51 1988 471 497
14. P. Tapolcsányi, J. Wölfling, G. Falkay, Á. Márki, R. Minorics, and Gy. Schneider Synthesis and receptor-binding examination of 16-hydroxymethyl-3,17-estradiol stereoisomers Steroids 67 2002 671 678
15. T. Ojasoo, and J.P. Raynoud Unique steroid congeners for receptor studies Cancer Res 38 1978 4186 4198
16. C. Martel, L. Provencher, X. Li, A. St. Pierre, G. Leblanc, and F. Gauthier Binding characteristics of novel nonsteroidal antiestrogens to the rat uterine estrogen receptors J Steroid Biochem Mol Biol 64 1998 199 205
17. E.M. Wilson, and F.S. French Binding properties of androgen receptors. Evidence for identical receptors in rat testis, epididymis, and prostate J Biol Chem 251 1976 5620 5629
18. R. Boschan, and S. Winstein The role of neighboring groups in replacement reactions. XXI. Front-side participation of the acetoxy group. Catalytic effect of acetic acid on glycols with hydrogen chloride J Am Chem Soc 78 1956 4921 4925
19. Gy. Schneider, I. Vincze, and Gy. Dombi Front side neighbouring group participation in the 16-hydroxymethylandrost-5-ene-3,17-diol series Tetrahedron 38 1982 2729 2732
20. Gy. Schneider, E. Meskó, L. Hackler, and Gy. Dombi Steroids. Part 32. Configurational analysis of 16-methyltestosterone derivatives J Chem Soc Perkin Trans 1 1985 1597 1600
21. D.M. Tanenbaum, Y. Wang, S.P. Williams, and P. Sigler Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains Proc Natl Acad Sci USA 95 1998 5998 6003
22. G.M. Anstead, K.E. Carlson, and J.A. Katzenellenbogen The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site Steroids 62 1997 268 303
23. K. Ponsold, J. Draffehn, and B. Schönecker Quantitative Struktur-Wirkungs-Beziehungen zwischen physikochemischen Parametern 16α-heterosubtituierter Östradiole und dem Bindungsvermögen an Rezeptoren des Rattenuterus in vitro Pharmazie 32 1977 596 597
24. A.M. Brzozowski, A.C.W. Pike, Z. Dauter, R.E. Hubbard, T. Bonn, and O. Engström Molecular basis of agonism and antagonism in the oestrogen receptor Nature 389 1997 753 758
25. K. Ekena, J.A. Katzenellenbogen, and B.S. Katzenellenbogen Determinants of ligand specificity of estrogen receptor-α: estrogen versus androgen discrimination J Biol Chem 273 1998 693 699