122566-22-7

Usage

Uses

Used in Pharmaceutical Industry:
(17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol is used as an intermediate compound for the preparation of Δ6-estrogens, which are important in the development of pharmaceuticals targeting hormonal imbalances and related conditions. Its unique structure allows for the creation of novel estrogenic compounds with potential therapeutic benefits.
Used in Research and Development:
In the field of research and development, (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol serves as a valuable tool for studying the effects of estrogenic substances on biological systems. It can be used to investigate the mechanisms of action of estrogens and to develop new drugs with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
(17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol can also be utilized as a starting material or building block in the synthesis of more complex organic molecules, particularly those with potential applications in the pharmaceutical, agrochemical, or materials science industries. Its unique functional groups and structural features make it a versatile component in organic synthesis.

Upstream product

• 3589-91-1 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene 
• 50-28-2 estradiol 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 1428627-89-7 4-{4-[6-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)-hex-1-ynyl]-phenyl}piperazine-1-carboxylic acid tert-butyl ester 
• 1428627-90-0 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene 
• 1428627-91-1 3-{4-[6-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)hex-1-ynyl]phenyl}3-oxopropionic acid ethyl ester 
• 1428627-92-2 2-{4-[6-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)-hex-1-ynyl]-benzyl}malonic acid diethyl ester 
• 1428627-93-3 3,17β-bis(hydroxy)-7α-[6-(4-pyrrol-1-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene 
• 1428627-94-4 3,17β-bis(hydroxy)-7α-[6-(4-piperidin-1-ylmethyl-phenyl)-hex-5-ynyl]-estra-1,3,5(10)-triene 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 862700-70-7 3,17β-bis(2-tetrahydropyranyloxy)-7α-[9-(4,4,5,5,5-pentafluoropentyl)thiononyl]estra-1,3,5(10)-triene-6-one 
• 129453-61-8 fulvestrant 
• 571-92-6 6-ketoestradiol 
• 7291-41-0 6-Dehydroestradiol 
• 408512-85-6 7α-[6-(N-(2-(tert-butyldimethylsilanyloxy)-ethyl)-diphenylphosphinamido)-hexan-1-yl]-estra-1,3,5(10)triene-3,17β-bis-2-tetrahydropyranyl ether 
• 740809-75-0 7α-[6-(N-(2-hydroxyethyl)-diphenylphosphinamido)-hexan-1-yl]-estra-1,3,5(10)triene-3,17β-bis-2-tetrahydropyranyl ether 
• 925673-28-5 N-butyl-N-methyl-7-(3-benzyloxy-2-iodo-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide 

Relevant academic research and scientific papers

Synthesis of novel estrogen receptor antagonists using metal-catalyzed coupling reactions and characterization of their biological activity

Estrogen receptor (ER) antagonists are valuable in the treatment of ER-positive human breast cancer. In this study, we designed and synthesized nine new derivatives of 17β-estradiol (E2) with a bulky side chain attached to its C-7α position, and determined their ER antagonistic activity using in vitro bioassays. Four of the derivatives showed a strong inhibition of ERα transactivation activity in a luciferase reporter assay and blocked ERα interactions with coactivators. Similarly, these derivatives also strongly inhibited the growth of the ERα-positive human breast cancer cells. Computational docking analysis was conducted to model the interaction of these antagonists with the human ERα and showed that they could tightly bind to the ERα in a manner similar to that of ICI-182,780, a pure ER antagonist. These results provide an example that attachment of a bulky side chain to the C-7α position of E2 can produce ER antagonists with ER affinity comparable to that of ICI-182,780.

Jostling for position: Optimizing linker location in the design of estrogen receptor-targeting PROTACs

Estrogen receptor-α (ER) antagonists have been widely used for breast cancer therapy. Despite initial responsiveness, hormone-sensitive ER-positive cancer cells eventually develop resistance to ER antagonists. It has been shown that in most of these resis

Process for the manufacture of 7-alpha-[9-(4,4,5,5,5-penta fluoropentylsulphinyl) nonyl]estra-1,3,5-(10)- triene-3,17-beta-diol

The present invention provides a novel multi-step process for the manufacturing Fulvestrant, which is economical and convenient to operate at commercial scale, and requires only simple chromatographic separations after the coupling step of adding the side chain to the 7 position of the steroid.

PROCESS FOR THE MANUFACTURE OF 7-ALPHA-[9-(4,4,5,5,5-PENTA FLUOROPENTVLSULPHINVL) NONVLLESTRA-L,3,5-(10)- TRIENE-3,17-BETA-DIOL

The present invention provides a novel multi-step process for the manufacturing Fulvestrant, which is economical and convenient to operate at commercial scale, and requires only simple chromatographic separations after the coupling step of adding the side chain to the 7 position of the steroid.

C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation

A series of estrone and estradiol derivatives having an N-butyl,methyl heptanamide side chain at C6-position were synthesized, tested as inhibitors of type 1 17β-HSD and assessed for their possible estrogenic activity. A better type 1 17β-HSD inhibition w

STEROIDS FOR CANCER TREATMENT

The present invention relates to novel compounds which are 7α-substituted 17-alkylene-16α-hydroxy steroidal estrogens. This invention specifically relates to estrogen derivatives which contain 7α-substituents and which exhibit anti-estrogenic properties. The present invention also relates to use of said compounds as a medicament, and for the treatment of estrogen dependent disorders, a pharmaceutical composition comprising one or more of said compounds and a method of treatment.

A rationally designed genotoxin that selectively destroys estrogen receptor-positive breast cancer cells

We describe a novel strategy to increase the selective toxicity of genotoxic compounds. The strategy involves the synthesis of bifunctional molecules capable of forming DNA adducts that have high affinity for specific proteins in target cells. It is propo

Synthesis and Binding Affinities of Novel Re-Containing 7α-Substituted Estradiol Complexes: Models for Breast Cancer Imaging Agents

The diagnosis and staging of breast cancer could be improved by the development of imaging radiopharmaceuticals that provide a noninvasive determination of the estrogen receptor status in the tumor cells. Toward this goal, we have synthesized a number of novel Re-containing 7α-substituted estradiol complexes. The introduction of the 7α side chain involves the alkylation of tetrahydropyranyloxy-protected 6-keto estradiol. The methods used to introduce the rhenium metal involve "3 + 1" and "4 + 1" mixed ligand complexes (2a-c and 5, respectively), tricarbonyl dithioether complexes (3), and the cyclopentadienyltricarbonylmetal organometallic system (4ab, 6, 7). These complexes showed binding affinities for the estrogen receptor (as high as 45% for the "3 + 1" complex 2c) when compared to the native ligand estradiol. The polarity of some complexes (4ab) was modified to improve biodistribution properties by introducing (poly)ether linkages into the 7α side chain (6, 7). These complexes provide a further refinement of our understanding of ligand structure-binding affinity correlations for the estrogen receptor, and they furnish the synthetic groundwork for the synthesis of the analogous Tc-99m complexes for evaluation as breast tumor imaging agents.