53573-82-3

Usage

Uses

Used in Pharmaceutical Industry:
(17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one is used as a precursor in the synthesis of antiestrogenic steroids. These antiestrogenic steroids are important for the development of medications that can counteract the effects of excess estrogen in the body, which can be beneficial in treating various conditions related to hormonal imbalances, such as certain types of cancer and endometriosis.
Used in Research and Development:
In addition to its pharmaceutical applications, (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one can also be utilized in research and development for studying the effects of estrogen and its role in various physiological processes. (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one can serve as a valuable tool in understanding the molecular mechanisms underlying estrogen-related diseases and in the development of novel therapeutic strategies.
Used in Drug Delivery Systems:
Similar to gallotannin, (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one can potentially be incorporated into drug delivery systems to improve the bioavailability and therapeutic outcomes of antiestrogenic steroids. By employing various organic and metallic nanoparticles as carriers, the compound can be more effectively delivered to target cells, enhancing its efficacy in treating conditions related to estrogen dysregulation.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 50-28-2 estradiol 
• 571-92-6 6-ketoestradiol 
• 122566-22-7 (8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ol 
• 3589-91-1 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene 

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 
• 251322-18-6 7α-(15-benzyloxy-7,10,13-trioxapentadecan-1-yl)-17β-(t-butyldimethylsilanyloxy)-3-(2-methoxyethoxymethoxy)estra-1,3,5(10)-triene 
• 251322-05-1 7α-[6-(S-benzoylthio)hexan-1-yl]-3,17β-bis(t-butyldimethylsilanyloxy)estra-1,3,5(10)-triene 
• 251322-26-6 3-(benzyloxy)-7α-(6-benzyloxy-4-oxahexan-1-yl)-17β-(t-butyldimethylsilanyloxy)estra-1,3,5(10)-triene 
• 251322-06-2 7α-[6-(S-benzoylthio)hexan-1-yl]estra-1,3,5(10)-triene-3,17β-diol 
• 251322-25-5 3-(benzyloxy)-17β-(t-butyldimethylsilanyloxy)-7α-(3-hydroxypropan-1-yl)estra-1,3,5(10)-triene 

Relevant academic research and scientific papers

Chemical synthesis and biochemical characterization of a biotinylated derivative of 17β-estradiol with a long side chain covalently attached to its C-7α position

High-affinity biotinylated derivatives of 17β-estradiol (E2) are of value for isolation of various estrogen-binding proteins (including estrogen receptors) and also for studying protein-protein interactions involving these proteins. In this study, we developed a simplified route for the chemical synthesis of a biotinylated derivative of E2 (compound 7) with a side chain attached to its C-7α position. Compound 7, i.e., 7α-{7-[8-(biotinamido)-octanamido]-heptyl}-estradiol, could be readily synthesized from 6-keto-estradiol-3,17β-di-tetrahydropyranyl ether (compound 2, which can be prepared from E2), with a final yield of 36%. In vitro receptor-binding assay confirmed that the synthesized affinity ligand has a high binding affinity for both human estrogen receptor α and β. When the affinity ligand (compound 7) was immobilized with avidin on an affinity column, it effectively bound human estrogen receptor α, and the receptor protein could be selectively eluted with a biotin-containing buffer. Using the same affinity ligand, prolyl 4-hydroxylase β-subunit (also known as protein disulfide isomerase) was identified as one of the high-affinity E2-binding proteins in the whole cytosolic protein mixture prepared from MCF-7 human breast cancer cells. Computational molecular modeling analysis showed that compound 7 can bind to human estrogen receptor α in a similar manner as ICI-182,780 and raloxifene, and their binding energy values are also similar.

PROCESS FOR THE PREPARATION OF FULVESTRANT

The present invention relates to an improved process for the preparation of Fulvestrant (I). Also, provided is novel intermediate of Fulvestrant and a process for the preparation of the same.

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

Design, synthesis, and estrogenic activity of a novel estrogen receptor modulator - A hybrid structure of 17β-estradiol and vitamin E in hippocampal neurons

We recently discovered that ICI 182,780 (1), an antagonist of estrogen receptor (ER)-dependent proliferation in reproductive tissues, functions as an estrogenic agonist in primary neurons. The present study investigated whether the agonist properties of 1 in neurons could be translated into structural analogs. 7α-[(4R,8R)-4,8,-12-trimethyltridecyl]estra-1,3,5-trien-3, 17β-diol (2), a hybrid structure of 17β-estradiol and vitamin E, was synthesized and found to bind to both ERα and ERβ. In vitro analyses demonstrated that 2 was neuroprotective and effective in activating molecular mechanisms associated with estrogenic agonist activity in rat primary hippocampal neurons. Collectively, the data support an estrogenic agonist profile of 2 action comparable to 1 in primary neurons, confirming that estrogenic activity of 1 in neurons is not a unique phenomenon. These results provide support for the development of a brain-selective ER modulator, with potential as an efficacious and safe estrogen alternative to prevent Alzheimer's disease and cognitive decline in postmenopausal women.

ENT-STEROIDS AS SELECTIVELY ACTIVE ESTROGENS

From EXEMP_CLAIMS : Ent-Steroids namely ent-Estriol ent-Estriol-3-sulfamate ent-Estriol-3-(N-acetyl)sulfamate ent-Estriol-3,16,17-tripropionate ent-Estrone-3-sulfamate ent-Estrone-3-(N-acetyl)sulfamate ent-Estradiol-3-sulfamate ent-Estradiot-3,17-disulfam

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.