15833-07-5

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C18H23BrO2/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-16(20)15(19)9-13(10)11/h8-9,11-12,14,17,20-21H,2-7H2,1H3

Upstream product

• 19590-55-7 2,4-dibromoestradiol 
• 113680-55-0 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 32158-57-9 estra-1,3,5(10)-triene-3,17β-diol 3-methoxymethyl ether 
• 50-28-2 estradiol 
• 15856-39-0 2-bromo-3,17β-estradiol diacetate 
• 113680-59-4 2-trimethylsilylestra-1,3,5(10)-triene-3,17β-diol 3,17-bis(methoxymethyl) ether 
• 113680-60-7 2-trimethylsilyl-1,3,5(10)-triene-3,17β-diol 3-methoxymethyl ether 
• 133586-87-5 2-phenylselenenylestradiol 
• 1474-52-8 17β-oestradiol diacetate 
• 50-28-2 estradiol 
• 15856-39-0 Acetic acid (13S,17S)-3-acetoxy-2-bromo-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester 

Downstream Products

• 686721-46-0 2-bromo-3-benzyloxyestra-1,3,5(10)-trien-17β-ol 
• 1818-12-8 2-Methyl-oestradiol 
• 26788-23-8 4-methoxy-17β-estradiol 
• 50-28-2 estradiol 
• 362-07-2 2-Methoxyestradiol 
• 5150-62-9 Estradiol 3,17-bis-TMS ether 

Relevant academic research and scientific papers

Electrochemical A-ring bromination of estrogens

A-ring bromination of estrogens has been achieved by constant current electrolysis of the solutions of these substrates and Et4NBr in appropriate solvents. Thus, electrolysis consuming 2 F mol-1 charge gave mixtures of 2- and 4-estrogens (1:1.1-2.5; up to 97%), whereas 4 F mol -1 charge experiments yielded 2,4-dibromoestrogens as the sole products.

Cross-coupling of [11C]methyllithium for 11C-labelled PET tracer synthesis

The cross-coupling of aryl bromides with [11C]CH3Li for the labelling of a variety of tracers for positron emission tomography (PET) is presented. The radiolabelled products were obtained in excellent yields, at rt and after short reaction times (3-5 min) compatible with the half-life of 11C (20.4 min). The automation of the protocol on a synthesis module is investigated, representing an important step towards a fast method for the synthesis of 11C-labelled compounds for PET imaging. This journal is

18F-labelling of A-ring substituted 16α-fluoro-estradiols as potential radiopharmaceuticals for PET imaging

The 2-methoxy derivative of estradiol is currently in Phase II clinical trial as an anticancer agent while the 4-methyl derivative has been shown to interact with cytoplasmic and nuclear estrogen receptors in rat pituitary gland and hypothalamus. We hypothesize that the 16α-18F-analogs of these estrogens could be suitable radiotracers to evaluate action mechanisms of the parent compounds. In this study we report the synthesis of the 16α-18F and 16α-19F-analogs of the A-ring substituted estradiols in high yield via stereoselective opening of the intermediate 16β,17β-O-cyclic sulfones with [18F]F- or F- followed by deprotection.

Chemical synthesis of six novel 17β-estradiol and estrone dimers and study of their formation catalyzed by human cytochrome P450 isoforms

Our earlier studies have shown that over 20 nonpolar 17β-estradiol metabolite peaks were detected following incubations of radioactive 17β-estradiol with human liver microsomes or recombinant human cytochrome P450 isoforms in the presence of NADPH as a co

Chemical synthesis of two novel diaryl ether dimers of estradiol-17β

We recently detected the formation of estradiol-17β (estradiol) dimers, linked together through a diaryl ether bond between the C-3 phenolic oxygen of one estradiol molecule and the 2- or 4-position aromatic carbon of another estradiol, following incubations of [3H]estradiol with human liver microsomes or cytochrome P450 enzymes in the presence of NADPH. Using estradiol as the starting material, we designed a four-step method for the chemical synthesis of these two estrogen dimers with the Ullmann condensation reaction as a key step. Step 1: Synthesis of 2- or 4-bromoestradiol from estradiol. Step 2: Protection of the C-3 phenolic hydroxyl group of the 2- or 4-bromoestradiol. Step 3: The Ullmann condensation reaction between the phenol-protected bromoestradiol and the estradiol potassium salt under our modified reaction conditions (with a 41% product yield). Step 4: Removal of the C-3 benzyl group by catalytic hydrogenation. The chromatographic and various spectrometric properties of the two synthesized compounds were identical to those metabolically formed by human cytochrome P450 3A4.

Reaction of Benzeneselenyl Halides with Estrogens

The reaction of estradiol and estrone with benzeneselenyl chloride affords mainly 2-phenylselenyl adducts which are readily converted into the corresponding 2-halogenated estrogens upon treatment with a variety of reagents.

Efficient regioselective a-ring functionalization of oestrogens

Complete series of 2-halo- and 2-cyano-oestrogens have been prepared in good to high yields: 2-chloro, 2-bromo, 2-iodo, and 2-cyano derivatives via oestrogen-thallium (III) bis(trifluoroacetate) intermediates, and 2- and 4- fluorooestrogens by direct functionalization using N-fluoropyridinium triflate.

An Alternative Route to 2-Bromo- and 2-Iodo-estradiols from Estradiol

Through careful choice of reaction conditions, alkylation of estradiol with chloromethyl methyl ether may yield either the 3,17β-bis(methoxymethyl) ether or the 3-methoxymethyl ether derivative.Treatment of either of these protected estradiols with s-butyllithium, then with trimethylsilyl chloride affords, regioselectively, the 2-trimethylsilyl derivatives which can conveniently be converted into 2-bromo- or 2-iodo-estradiol.

A NEW SYNTHETIC ROUTE TO 2- AND 4-METHOXYESTRADIOLS BY NUCLEOPHILIC SUBSTITUTION

A new synthetic route to 2- and 4-methoxyestradiols is described.Benzo-15-crown-5 with CuI catalyzes the specific nucleophilic substitution at the carbon atom carrying a non-activated halogen on ring A of the estradiol.

Synthesis of 2-Methoxy- and 4-Methoxy-Estrogens with Halogen-Methoxy Exchange Reaction

Synthesis of 2-methoxy- and 4-methoxy-estrone (6) and (9), 2-methoxy- and 4-methoxy-estradiol (15) and (18), and 2-methoxy- and 4-methoxy-estratriol (24) and (27) are described.Catalytic hydrogenation over Pd/C of 2,4-dibromo or 2,4-diiodo estrogens gave regioselectively the corresponding 4-halogeno derivatives in excellent yields.Reaction of 2-iodo or 4-iodo estradiol and 2-iodo or 4-iodo estriol with NaOCH3 in MeOH and dimethylformamide (DMF) in the presence of CuCl2 gave in an excellent yield and in a good yield, while (6) and (9) were also similarly obtained by the reaction with pyridine instead of DMF.