1630-83-7

Basic information

• Product Name: 4-BROMOESTRADIOL
• Synonyms: 1,3,5(10)-ESTRATRIEN-4-BROMO-3,17-BETA-DIOL;4-BROMOESTRADIOL;4-Bromo-17β-estradiol;4-Bromo 172-Estradiol
• CAS NO: 1630-83-7
• Molecular Formula: C₁₈H₂₃BrO₂
• Molecular Weight: 351.28
• Product Categories: Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 1630-83-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 455.4°Cat760mmHg
• Flash Point: 229.2°C
• Appearance: /
• Density: 1.411g/cm³
• Vapor Pressure: 4.39E-09mmHg at 25°C
• Refractive Index: 1.618
• Solubility: Methanol
• CAS DataBase Reference: 4-BROMOESTRADIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOESTRADIOL(1630-83-7)
• EPA Substance Registry System: 4-BROMOESTRADIOL(1630-83-7)

Safety Data

• Hazardous Substances Data: 1630-83-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Solid

Uses

17β-Estradiol (E888000) metabolite. An inhibitor of androstenedione aromatization, which is responsible for the conversion of androgens to estrogens. Agonistic ligands for the estrogen receptor in MCF-7 breast cancer cells.

InChI:InChI=1/C18H23BrO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h4,6,11-12,14,16,20-21H,2-3,5,7-9H2,1H3

Upstream product

• 19590-55-7 2,4-dibromoestradiol 
• 50-28-2 estradiol 
• 15833-06-4 4-bromo-3,17β-estradiol diacetate 
• 80108-79-8 4-bromo-2-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol 

Downstream Products

• 686721-45-9 C₄₃H₅₂O₄ 
• 6171-48-8 4-Methyl-oestradiol 
• 1630-82-6 4-bromo-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 5150-62-9 Estradiol 3,17-bis-TMS ether 
• 50-28-2 estradiol 
• 686721-44-8 4-bromoestradiol 3-O-benzyl ether 
• 26788-23-8 4-methoxy-17β-estradiol 
• 55898-45-8 4-(trimethylsilyl)estra-1,3,5(10)-triene-3,17β-diol 

Relevant articles and documents

Synthesis and Antitumor Evaluation of Novel Hybrids of Phenylsulfonylfuroxan and Estradiol Derivatives

Fifteen novel furoxan-based nitric oxide (NO) releasing hybrids of estradiol derivatives were synthesized and evaluated in vitro anti-proliferative activity in MDA-MB-231, A2780, Hela and HUVEC cell lines. Most of them displayed potent anti-proliferative effects. Among the compounds, 4-bromo-3-((phenylsulfonyl)-1,2,5-oxadiazole 2-oxide)-oxy-propoxy-estradiol (11 b) exhibited the best activity with IC50 values of 3.58–0.0008 μM. Preliminary pharmacological studies showed that 11 b induced apoptosis and hardly affected the cell cycle of MDA-MB-231 cell line. NO-releasing capacity and inhibition of ERK/MAPK pathway signaling might explain the potent antineoplastic activity of these compounds. The preliminary structure-activity relationship (SAR) showed that steroidal scaffolds with a linker in 3-position were favorable moieties to evidently increase the bioactivities of these hybrids. Overall, these results implied that 11 b merited to be further investigated as a promising anti-cancer candidate.

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.