71765-95-2Relevant academic research and scientific papers
PREPARATION OF 16-SUBSTITUTED 3-HYDROXYESTRA-1,3,5(10)-TRIENE-17-ONE STARTING WITH THE BROMINATION OF ESTRONE ACETATE
Fedorova, O. I.,Morozova, L. S.,Alekseeva, L. M.,Grinenko, G. S.
, p. 437 - 440 (2007/10/02)
The bromination of estrone acetate (Ia) leads to a mixture of acetates of 16α-bromo-16β-bromo-, and 16,16-dibromoestrone (IIa, IIIa, and IVa) in a ratio of 63:28:9.On treatment with an aqueous methanolic solution of potash, depending on the conditions, a mixture of (IIa) and (IIIa) gives 3,16α-dihydroxyestra-1,3,5(10)-trien-17-one (V) or 3,17β-dihydroxyestra-1,3,5(10)-trien-16-one (VI).When 5 g of (Ia) was brominated with 2.8 g of Br2 in chloroform and the products were chromatographed on silica gel, 0.36 g of (IVa), C20H22Br2O3, mp 165-166 deg C (from ether) 0.37 g of (IIIa), mp 169-170.5 deg C, 4.6 g of a mixture of (IIa) and (IIIa), 30 mg of (Ia) and 0.2 g of a mixture of 16α- and 16β-bromoestrones was obtained.The action of potash on a mixture of (IIa) and (IIIa) in aqueous MeOH at 20 deg C led to the epimerization of the (IIa) into (IIIa) and then the conversion of the latter into (V) with mp 203.5-206 deg C; diacetate with mp 172-173 deg C (acetone-ethanol).Similarly, but with heating (98 deg C, 3 h), a mixture of (IIa) and (IIIa) was converted into (VI), with mp 234-236 deg C.Characteristics of the IR and PMR spectra of the compounds obtained are given.
STRUCTURE-ACTIVITY RELATIONSHIPS OF ESTROGENS, EFFECTS OF 14-DEHYDROGENATION AND AXIAL METHYL GROUPS AT C-7, C-9 AND C-11
Gabbard, R. Bruce,Segaloff, Albert
, p. 791 - 805 (2007/10/02)
Thirty compounds were evaluated in the rat for uterotropic effects, inhibition of gonadotropin release, and competitive displacement of (3H) estradiol-17β from uterine cytosolic preparations. 7α-Methylestradiol-17β was 150percent as active as estradiol-17β as an uterotropic agent.Estradiol-17β was the most active inhibitor of gonadotropin release. 11β-Methylestradiol-17β had 124percent of the activity of estradiol-17β in displacing (3H) estradiol-17β from the "estrogen receptor." The 9α-methyl group considerably decreased the potency of estrogens in any of the three assays.The 14-dehydromodification was advantageous only in the estradiol-17β 3-methyl ether series.Uterotropic activities and inhibition of gonadotropin release did not parallel.The best compound for inhibiting gonadotropin release, as compared to uterotropic activity, was estrone.The "estrogen receptor" assay data correlated fairly well with uterotropic assay data, but only for compounds having free 3-hydroxyl groups; even so, some exceptions were noted.
Syntheses of Seleno Estrogens
Arunachalam, Thangavel,Caspi, Eliahu
, p. 3415 - 3420 (2007/10/02)
The syntheses of phenylseleno and methylseleno analogues of estradiol are described.
A short efficient synthesis of 16-oxygenated estratriene 3-sulfates
Numazawa, Tohoku,Kimura, Katsuhiko,Nagaoka, Masao
, p. 557 - 566 (2007/10/02)
A novel synthesis of sodium 17-oxo-16α-hydroxy-1,3,5(10)-estratrien-3-yl sulfate (4), sodium 16α,17β-dihydroxy-1,3,5(10)-estratrien-3-yl sulfate (5) and sodium 16-oxo-17β-hydroxy-1,3,5(10)-estratrien-3-yl sulfate (6) is described. 16α-Bromo-3-hydroxy-1,3,5(10)-estratrien-17-one (1) was efficiently sythesized in one step with 70-97percent yield by bromination of 3-hydroxy-1,3,5(10)-estratrien-17-one with cupric bromide. 3,16α-Dihydroxy-1,3,5(10)-estratrien-17-one (3) was quantitatively obtained by controlled stereospecific hydrolysis of the bromoketone 1 with sodium hydroxide in aqueous pyridine.The bromoketone 1 was converted to the 16α-hydroxy-17-ketone 3-sulfate 4 by sulfation with chlorosulfonic acid in pyridine and a subsequent controlled hydrolysis in a high yield without formation of the other ketols.Treatment of the sulfate 4 with sodium borohydride gave the triol sulfate 5.The sulfate 4 was also rearranged to the 17β-hydroxy-16-ketone 6 with sodium hydroxide in water in a quantitative yield.
Estrogen receptor based imaging agents. 1. Synthesis and receptor binding affinity of some aromatic and D-ring halogenated estrogens
Heiman,Senderoff,Katzenellenborgen,Neeley
, p. 994 - 1002 (2007/10/02)
Steroidal and nonsteroidal estrogens substituted with halogens ortho to the phenolic hydroxyl group and in the D ring at C-16 have been prepared as potential estrogen receptor-based imaging agents for human breast tumors. Estrogens bearing an aromatic flu
