6714-06-3Relevant articles and documents
An efficient procedure for the regiospecific preparation of D-homo-steroid derivatives
Pellicciari,Natalini,Fringuelli
, p. 433 - 441 (1987)
α-Diazo-β-hydroxy esters 3, obtained by condensation of ketones 1 with ethyl diazo(lithio)acetate 2, are efficiently converted into the corresponding β-ketoesters 4 by exposure to dirhodium (II) tetraacetate. Application of this two-step sequence to 3β-acetoxy-5-androstene-17-one 5b and to 3-acetoxy estrone 10b afforded regiospecifically and in very high overall yield the corresponding ethyl 17a-oxo-D-homo-steroid-17-carboxylates 7a,b and 12a,b, which were decarboalkoxylated to give, respectively, 3β-hydroxy-D-homo-5-androstene-17a-one 8 and D-homoestrone 13.
Syntheses and antiproliferative effects of d-homo- and d-secoestrones
Mernyák, Erzsébet,Szabó, Johanna,Bacsa, Ildikó,Huber, Judit,Schneider, Gyula,Minorics, Renáta,Bózsity, Noémi,Zupkó, István,Varga, Mónika,Bikádi, Zsolt,Hazai, Eszter,W?lfling, János
, p. 128 - 136 (2014/07/21)
Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.
New methylene homologation method for cyclic ketones
Liu, Huaqing,Sun, Chunrui,Lee, Nam-Kyu,Henry, Roger F.,Lee, Daesung
supporting information, p. 11889 - 11893 (2012/10/29)
Teaching new tricks to an old dog: By intercepting adducts between ketones and lithium trimethylsilyldiazomethane, a new Tiffeneau-Demjanov type methylene homologation could be realized in a single-step operation. Among proton sources and Lewis acids, silica gel was found to be the most effective reagent for the protonation of intermediates and their subsequent ring expansion (see scheme). Copyright
Structure-based design, synthesis and in vitro characterization of potent 17β-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone
Moeller, Gabriele,Deluca, Dominga,Gege, Christian,Rosinus, Andrea,Kowalik, Dorota,Peters, Olaf,Droescher, Peter,Elger, Walter,Adamski, Jerzy,Hillisch, Alexander
scheme or table, p. 6740 - 6744 (2010/06/12)
In search for specific drugs against steroid-dependent cancers we have developed a novel set of potent inhibitors of steroidogenic human 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD 1). The X-ray structure of 17β-HSD 1 in complex with estradiol served
Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers
Woelfling, Janos,Mernyak, Erzsebet,Frank, Eva,Falkay, George,Marki, Arpad,Minorics, Renata,Schneider, Gyula
, p. 277 - 288 (2007/10/03)
An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13α-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13α-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17β-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13α-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13α-D-homoestrone derivatives are estrogen receptor-selective molecules.
Reactions of 3-Phenylthiobut-3-en-2-one. Part 4. Novel and Efficient Synthesis of 7-hydroxycalamenene, Ferruginol, and D-Homoestrone
Takaki, Ken,Ohsugi, Masakatsu,Okada, Michikazu,Yasumura, Masateru,Negoro, Kenji
, p. 741 - 745 (2007/10/02)
The annelation reaction of 3-phenylthiobut-3-en-2-one with carvomenthone (1) gives 8a-hydroxy-4α-isopropyl-1-methyl-6-phenylthioperhydronaphthalen-7-one (2), which is converted into 7-hydroxycalamenene (4) by subsequent dehydration, methylation, and aroma
