60788-62-7

Usage

Uses

Used in Medical Imaging:
2,4-DibroMo Estrone is used as a diagnostic agent for tumor imaging. Its application in this field is due to its potential to enhance the visualization and detection of tumors, aiding in the early diagnosis and treatment planning for cancer patients.
Used in Pharmaceutical Research:
As a metabolite of 2,4-Dibromo-17β-estradiol, 2,4-DibroMo Estrone may also be used in pharmaceutical research for the development of new drugs targeting hormone-related conditions or cancer therapies. Its chemical properties and interaction with biological systems make it a valuable compound for further investigation and potential application in drug discovery.

Upstream product

• 53-16-7 Estrone 

Downstream Products

• 53-16-7 Estrone 
• 1630-82-6 4-bromo-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 76048-16-3 2,4-diphenyl-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 95125-87-4 2-monobromestrone 
• 14984-43-1 2-Aminoestrone 
• 58562-33-7 4-methoxyestrone 
• 734-32-7 estra-4-ene-3,17-dione 

Relevant academic research and scientific papers

New estrone oxime derivatives: Synthesis, cytotoxic evaluation and docking studies

The interest in the introduction of the oxime group in molecules aiming to improve their biological effects is increasing. This work aimed to develop new steroidal oximes of the estrane series with potential antitumor interest. For this, several oximes were synthesized by reaction of hydroxylamine with the 17-ketone of estrone derivatives. Then, their cytotoxicity was evaluated in six cell lines. An estrogenicity assay, a cell cycle distribution analysis and a fluorescence microscopy study with Hoechst 3358 staining were performed with the most promising compound. In addition, molecular docking studies against estrogen receptor α, steroid sulfatase, 17β-hydroxysteroid dehy-drogenase type 1 and β-tubulin were also accomplished. The 2-nitroestrone oxime showed higher cytotoxicity than the parent compound on MCF-7 cancer cells. Furthermore, the oximes bearing halogen groups in A-ring evidenced selectivity for HepaRG cells. Remarkably, the ?9,11-estrone oxime was the most cytotoxic and arrested LNCaP cells in the G2 /M phase. Fluorescence microscopy studies showed the presence of condensed DNA typical of prophase and condensed and fragmented nuclei characteristic of apoptosis. However, this oxime promoted the proliferation of T47-D cells. Interestingly, molecular docking studies estimated a strong interaction between ?9,11-estrone oxime and estrogen receptor α and β-tubulin, which may account for the described effects.

Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons

Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.

?9,11-Estrone derivatives as potential antiproliferative agents: synthesis, in vitro biological evaluation and docking studies

A series of ?9,11-estrone derivatives with A- and D-ring modifications has been synthesized and evaluated as antiproliferative agents. The cytotoxicity was assessed in six cell lines (MCF-7, T47-D, LNCaP, HepaRG, Caco-2 and NHDF) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and a cell cycle distribution analysis was performed by flow cytometry. Some compounds exhibited relevant cytotoxicity, particularly ?9,11-estrone, which was the most active against HepaRG cells (IC50 = 6.67 μM). Besides the relevance of the double bond in the C-ring, the presence of a 16E-benzylidene group increased the antiproliferative effect on MCF-7 and T47-D cells. Moreover, the introduction of iodine in positions 2 and 4 of estrone seemed to induce a selective cytotoxicity for HepaRG cells. Flow cytometry experiments evidenced a 34% reduction of HepaRG cell viability after treatment with ?9,11-estrone and a cell cycle arrest at the G0/G1 phase. Estrogenic activity was also observed for this compound at 0.1 μM in T47-D cells, and molecular docking studies estimated a marked interaction between this compound and the estrogen receptor α.

Synthesis and structure–activity relationships of 2- and/or 4-halogenated 13β- and 13α-estrone derivatives as enzyme inhibitors of estrogen biosynthesis

Ring A halogenated 13α-, 13β-, and 17-deoxy-13α-estrone derivatives were synthesised with N-halosuccinimides as electrophile triggers. Substitutions occurred at positions C-2 and/or C-4. The potential inhibitory action of the halogenated estrones on human aromatase, steroid sulfatase, or 17β-hydroxysteroid dehydrogenase 1 activity was investigated via in vitro radiosubstrate incubation. Potent submicromolar or low micromolar inhibitors were identified with occasional dual or multiple inhibitory properties. Valuable structure–activity relationships were established from the comparison of the inhibitory data obtained. Kinetic experiments performed with selected compounds revealed competitive reversible inhibition mechanisms against 17β-hydroxysteroid dehydrogenase 1 and competitive irreversible manner in the inhibition of the steroid sulfatase enzyme.

Chemoselective Suzuki-Miyaura reactions of 4-bromo-3-O-triflyl-estrone. Synthesis and atropisomerism of arylated estrones

4-Bromo-3-O-triflyl-estrone has been synthesized in 2 steps from estrone and was successfully employed in chemoselective palladium catalysed Suzuki-Miyaura reactions. Mono- and bis-arylations were carried out selectively by variation of ligands and solven

Synthesis, functionalization and biological activity of arylated derivatives of (+)-estrone

Various novel arylated estrone derivatives, such as 2-aryl-, 4-aryl- and 2,4-diaryl-estrones, by Suzuki-Miyaura reactions. While the synthesis of 4-arylestrones could be carried out under standard conditions, the synthesis of 2-arylestrones and 2,4-diarylestrones required a thorough optimization of the conditions and it proved to be important to use sterically encumbered biaryl ligands. The best results were obtained by the use of RuPhos. Combination of developed Suzuki coupling reactions with subsequent cyclization reactions afforded more complex hybrid structures, containing dibenzofuran, benzocoumarin and steroid moieties. These derivatives were tested as pancreatic lipase inhibitors and it was found that most of the compounds exhibited inhibition of pancreatic lipase but the maximum inhibitory potential was shown by 4-arylestrones. All of the synthesized derivatives showed inhibitory values in the range of 0.82 ± 0.01–59.7 ± 3.12 μM. The biological activity was also rationalized on the bases of docking studies.

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.

TOPICAL ANTIANDROGENIC STEROIDS

Steroidal antiandrogens and pharmaceutical compositions thereof, are used for reduction of the risk of developing, or for treatment of, androgen-dependent skin related diseases. In preferred embodiments, the antiandrogen EM-3180 is used for reduction of t

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

REGIOSELECTIVE SYNTHESIS OF A-RING HALOGENATED DERIVATIVES OF 17α-ETHYNYLOESTRADIOL

C-2 and C-4 fluorinated and brominated derivatives of 17α-ethynyl-oestradiol have been efficiently prepared via the corresponding halo-oestrones