19590-55-7

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DIBROMOESTRADIOL is used as a research compound for studying its anti-cancer effects, specifically in hormone-sensitive tumors like breast cancer. Its ability to inhibit the growth of cancer cells makes it a promising candidate for further investigation and potential development as a therapeutic agent.
Used in Cancer Research:
In the field of cancer research, 2,4-DIBROMOESTRADIOL is utilized as a tool to explore the mechanisms by which it inhibits the growth of breast cancer cells. Understanding these mechanisms could lead to the development of novel therapeutic strategies for treating hormone-sensitive cancers.
Used in Drug Metabolism Studies:
2,4-DIBROMOESTRADIOL is employed as an inhibitor of cytochrome P450 enzymes in drug metabolism studies. Its potent inhibitory effects allow researchers to investigate the role of these enzymes in the metabolism of various drugs and hormones, potentially leading to the discovery of new drug interactions and metabolic pathways.

InChI:InChI=1/C18H22Br2O2/c1-18-7-6-9-10(13(18)4-5-15(18)21)2-3-11-12(9)8-14(19)17(22)16(11)20/h8-10,13,15,21-22H,2-7H2,1H3

Upstream product

• 64-17-5 ethanol 
• 50-28-2 estradiol 
• 79-15-2 N-bromoacetamide 
• 15087-02-2 estradiol-17β 17-(β-D-glucuronide) sodium salt 

Downstream Products

• 1630-83-7 4-bromo-β-estradiol 
• 50-28-2 estradiol 
• 434-22-0 19-nortestosterone 
• 15833-07-5 2-bromoestradiol 
• 26788-23-8 4-methoxy-17β-estradiol 
• 362-05-0 2-Hydroxyestradiol 
• 6301-87-7 2-Aminoestratriene-3,17beta-diol 
• 549-02-0 10β,17β-dihydroxyestra-1,4-dien-3-one 
• 15087-02-2 estradiol-17β 17-(β-D-glucuronide) sodium salt 

Relevant academic research and scientific papers

A NEW SYNTHETIC ROUTE TO PYROGALLOLESTROGEN DIMETHYL ETHERS BY NUCLEOPHILIC SUBSTITUTION OF 2,4-DIBROMOESTROGENS

A novel synthetic route to pyrogallolestrogen dimethyl ethers was developed.Benzo-15-crown-5 with CuI catalyses the specific nucleophilic substitution of bromo atoms by methoxide ions.

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.

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.

Synthesis of analogs of 2-methoxyestradiol with enhanced inhibitory effects on tubulin polymerization and cancer cell growth

A new series of estradiol analogs was synthesized in an attempt to improve on the anticancer activity of 2-methoxyestradiol, a naturally occurring mammalian tubulin polymerization inhibitor. The compounds were evaluated as inhibitors of tubulin polymeriza

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.

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.

Novel and Efficient Synthesis of Estriol and its 16-Glucuronide via 2,4,16α-Tribromoestrone

A novel synthesis of estra-1,3,5(10)-triene-3,16α,17β-triol (5), sodium 3,17β-dihydroxyestra-1,3,5(10)-trien-16α-yl-β-D-glucopyranosuronate (12b) aand sodium 3-hydroxyestra-1,3,5(10)-trien-17β-yl-β-D-glucopyranosuronate (10b) is described. 2,4,16α-Tribromo-3-hydroxyestra-1,3,5(10)-trien-17-one (2a) was efficiently synthesized in one step with quantitative yield by bromination of 3-hydroxyestra-1,3,5(10)-trien-17-one (1) with cupric bromide.Treatment of (2a) with NaOH in aqueous pyridine under the controlled conditions gave the 16α-hydroxy-17-ketone (4a) without ketol rearrangement.The ketol (4a) was converted in quantitative yield into the triol (5) via a sodium borohydride reduction in the presence of palladium chloride.Reaction of (4a) with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranosuronate using silver carbonate as a catalyst yielded the 16-monoglucuronide acetate methyl ester (11).The reductive removal of the bromines of (11) with sodium borohydride followed by NaOH hydrolysis gave the glucuronide (12b).A direct glucuronidation of 2,4-dibromoestra-1,3,5(10)-triene-3,17β-diol (8) and a subsequent hydrolysis of the 17-glucuronide (9) gave the glucuronide (10b).