Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers

Steroids

Volumn 68, Issue 3, 2003, Pages 277-288

  Wölfling, János ^a   Mernyák, Erzsébet ^a   Frank, Éva ^a   Falkay, George ^a   Márki, Árpád ^a   Minorics, Renáta ^a   Schneider, Gyula ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

13 epi Estrone derivatives; D Homosteroids; Estrogen receptor binding

Indexed keywords

1,2 PHENYLENEDIAMINE; 16ALPHA ETHYL 21 HYDROXY 19 NORPREGN 4 ENE 3,20 DIONE; 3 HYDROXY 13ALPHA DEXTRO HOMOESTRA 1,3,5(10) TRIEN 17A ONE; 3 HYDROXY DEXTRO HOMOESTRA 1,3,5(10) TRIEN 17A ONE; 3 METHOXY 13ALPHA DEXTRO HOMOESTRA 1,3,5(10) TRIEN 17A ONE; 3 METHOXY DEXTRO HOMOESTRA 1,3,5(10) TRIEN 17A ONE; ESTRADIOL; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR; ESTRONE DERIVATIVE; ETHER DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EPIMERIZATION; FEMALE; HORMONE RECEPTOR INTERACTION; IN VITRO STUDY; NONHUMAN; RADIOASSAY;

HOMO;

EID: 0037333882     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(02)00181-2     Document Type: Article

References (42)

1. Baulieu EE. Hormones, a complex communications network. In: Baulieu EE, Kelly PA, editors. Hormones. Paris: Herman Publishers, and New York: Chapman & Hall; 1990. p. 147.
2. Tapolcsányi P., Wölfling J., Falkay G., Márki Á., Minorics R., Schneider G. Synthesis and receptor-binding examination of 16-hydroxymethyl-3,17-estradiol stereoisomers. Steroids. 67:2002;671-678.
3. Gao H., Katzenellenbogen J.A., Garg R., Hansch C. Comparative QSAR analysis of estrogen receptor ligands. Chem. Rev. 99:1999;723-744.
4. Claussner A., Nédelec L., Nique F., Philibert D., Teutsch G., Van de Velde P. 11β-Aminoalkyl estradiols, a new series of pure antiestrogens. J. Steroid Biochem. Mol. Biol. 41:1992;609-614.
5. Diorazio L.J., Widdowson D.A., Clough J.M. Regiospecific synthesis of 2-fluoro-3-O-methylestrone using caesium fluorosulfate. J. Chem. Soc., Perkin Trans. 1:1992;421-426.
6. Pennington W.T., Resnati G., DesMarteau D.D. Para-fluorination by N-fluorobis[(trifluoromethyl)sulfonyl]imide: synthesis of 10β-fluoro-3-oxo-1,4-estradiene steroids. J. Org. Chem. 57:1992;1536-1539.
7. Lotz W. Biological activities and receptor affinities of some natural and synthetic oestrogens and their D-homo analogues. Experimentia. 34:1978;1373-1374.
8. Ananchenko S.N., Limanov V.Y., Leonov V.N., Rzheznikov V.N., Torgov I.V. Syntheses of derivatives of oestrane and 19-norsteroids from 6-methoxytetralone and 6-hydroxytetralone. Tetrahedron. 18:1962;1355-1367.
9. Bull J.R., Steer L.M. Intramolecular condensation of steroidal 17α-formyl-17β-acetates: model studies on 19-norsteroids, and a route to 3-methoxy-19-nor-17α-pregna-1,3,5(10)-triene-21,17-carbolactone. Tetrahedron. 46:1990;5389-5400.
10. Forcellese M.L., Camerini E., Ruffini B., Mincione E. D-homo steroids from oxidation of 17-methylene steroids by thallium(III) nitrate. J. Org. Chem. 46:1981;3326-3328.
11. 1H NMR method for the determination of configuration of hydroxyl group in position 5 and/or 14 of the D-homo-steroid skeleton Collect Czech. Chem. Commun. 56:1991;1512-1524.
12. Schönecker B., Lange C., Kötteritzsch M., Günther W., Weston J., Anders E. et al. Conformational design for 13α-steroids. J. Org. Chem. 65:2000;5487-5497.
13. Goldberg M.W., Studer S. D-homooestron. Helv. Chim. Acta. 24:1941;478-482.
14. Ojasoo T., Raynaud J.P. Unique steroid congeners for receptor studies. Cancer Res. 384:1978;186-198.
15. Schneider G, Bottka S, Hackler L, Wölfling J, Sohár P. Neighbouring group participation and fragmentation during the solvolysis of the epimers of 3-methoxy-16-(tolylsulfonyloxymethyl)-estra-1,3,5(10)triene-17-ol. Liebigs Ann Chem 1989;263-7.
16. Tietze L.F., Schneider G., Wölfling J., Fecher A., Noebel T., Petersen S. et al. A novel approach in drug discovery: synthesis of estrone-talaromycin natural product hybrids. Chem. Eur. J. 6:2000;3755-3760.
17. Yaremenko F.G., Khvat A.V. A new one-pot synthesis of 17-oxo-13α-steroids of the androstane series from their 13β-analogues. Mendeleev Commun. 4:1994;187-188.
18. Schönecker B. Personal communication.
19. Appel R, Halstenberg M. Functional group conversions using phosphorus(III) reagents and polyhalogenoalkanes. In: Cadogan JIG, editor. Organophosphorus reagents in organic synthesis. New York: Academic Press; 1979. p. 387-431.
20. Fujita T., Tanaka M., Norimine Y., Suemune H., Sakai K. Enantioselective synthesis of (-)-curcumanolide a using enzymatic transesterification of meso-spirodiol. J. Org. Chem. 62:1997;3824-3830.
21. Bollbuck B., Tochtermann W. Novel chiral building blocks derived from Baker's yeast reduction products: synthesis and odour of mono- and bicyclic macrolides. Tetrahedron. 55:1999;7191-7208.
22. Timár Z., Kovács L., Kovács G., Schmél Z. Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers. J. Chem. Soc., Perkin Trans. 1:2000;19-26.
23. Camp D., Jenkins I.D. The use of a phosphine containing a basic group in the Mitsunobu esterification reaction. Aust. J. Chem. 41:1988;1835-1839.
24. Bull J.R., Mountford P.G., Kirsch G., Neef G., Müller-Fahrnow A., Wiechert R. Cycloaddition-fragmentation route to 14β-allylestrone and the derived 14α,17α-ethano analogue of estriol. Tetrahedron. 50:1994;6363-6376.
25. Bull JR, de Koning PD. Diels-Alder cycloadditions of 3-methoxy-8α-estra-1,3,5(10),14,16-pentaen-17-yl acetate: unexpected trends in regioselectivity. Synthesis 2000;1761-5.
26. Grob C.A., Schiess P.W. Die heterolische Fragmentierung als Reaktionstypus in der organischen Chemie. Angew Chem. 79:1967;1-14.
27. Wölfling J, Frank É, Schneider G, Bes MT, Tietze LF. Synthesis of azasteroids and D-homosteroids by intramolecular cyclization reactions of steriod arylimines. Synlett 1998;1205-6.
28. Wölfling J, Frank É, Schneider G, Tietze LF. Synthesis of novel steroid alkaloids by cyclization of arylimines from estrone. Eur J Org Chem 1999;3013-20.
29. Frank É, Mernyák E, Wölfling J, Schneider G. Stereoselective synthesis of new halogen-containing D-homoestrone derivatives. Synlett 2002;419-22.
30. Johns W.F., Salamon K.W. Synthesis and reactions of 17β-oxygenated 16α,17-cyclopropylandrostanes. J. Org. Chem. 36:1971;1952-1962.
31. Wölfling J., Frank É., Mernyák E., Bunkóczi G., Cvesta Seijo J.A., Schneider G. Synthesis of novel halogen-containing D-homoestrone and 13α-D-homoestrone derivatives by Lewis acid-induced intramolecular Prins reaction. Tetrahedron. 58:2002;6851-6861.
32. Dougles GH, Graves JMH, Hartley D, Hughes GA, McLoughlin BJ, Siddall J, et al. Totally synthetic steroid hormones. Oestrone and related oestrapolyenes. J Chem Soc 1963;5072-94.
33. Gutzwiller J., Meier W., Fürst A. Totalsynthese von (+)-D-homoöstron-3-methyläther. Helv. Chim. Acta. 60:1977;2258-2269.
34. Takaki K., Ohsugi M., Okada M., Yasumura M., Negoro K. Reactions, of 3-phenylthiobut-3-en-2-one. Novel and efficient synthesis of 7-hydroxycalamenene, ferruginol, and D-homoestrone. J. Chem. Soc., Perkin. Trans. 1:1984;741-745.
35. Schneider M.R., von Angerer E., Prekajac J., Brade W.P. Studies on the mammary-inhibiting effects of diethylstilbestrol and its mono- and diphosphate. J. Cancer Res. Clin. Oncol. 111:1986;110-114.
36. Wakeling A.E., Valcaccia B., Newboult E., Green L.R. Non-steroidal antioestrogens - receptor binding and biological response in rat uterus rat mammary carcinoma and human breast cancer cells. J. Steroid Biochem. 20:1984;111-120.
37. Sun J., Meyers M.J., Fink B.E., Rajendran R., Katzenellenbogen J.A., Katzenellenbogen B.S. Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-α or estrogen receptor-β Endocrinology. 140:1999;800-804.
38. Mortensen D.S., Rodriguez A.L., Carlson K.E., Sun J., Katzenellenbogen B.S., Katzenellenbogen J.A. Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor α J. Med. Chem. 44:2001;3838-3848.
39. Tanenbaum D.M., Wang Y., Williams S.P., Sigler P.B. Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains. Proc. Natl. Acad. Sci. U.S.A. 95:1998;5998-6003.
40. Ekena K., Weis K.E., Katzenellenbogen J.A., Katzenellenbogen B.S. Different residues of the human estrogen receptor are involved in the recognition of structurally diverse estrogens and antiestrogens. J. Biol. Chem. 272:1997;5069-5075.
41. Williams S.P. Sigler P.B. Atomic structure of progesterone complexed with its receptor. Nature. 393:1998;392-396.
42. Mernyák E, Wölfling J, Bunkóczi G, Luo L, Schneider TR, Schneider G. Stereoselective synthesis of the two trans 16-hydroxymethyl-3-methoxy-13a-estra-1,3,5(10)-trien-17-ol isomers. Collect Czech Chem Commun, submitted for publication.