Category: 63675-74-1

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63675-74-1, Name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene, belongs to benzothiophene compound, is a common compound. Recommanded Product: 63675-74-1In an article, once mentioned the new application about 63675-74-1.

Intermediates and a process for preparing benzo[b]thiophenes

The present invention provides a process for preparing a class of compounds having the structure wherein: n is 0, 1, or 2; R is hydrogen or C1-C4 alkyl; X1 is hydrogen, cyano, 4-hydroxybenzoyl, 4-halobenzoyl, or 4-(C1-C4 alkoxy)benzoyl; Y is NR4R5, 4-hydroxyphenyl, or 4-(C1-C4 alkoxy)phenyl; R4 and R5 are independently hydrogen or C1-C4 alkyl. The compounds are useful intermediates in the preparation of a class of compounds including the selective estrogen receptor modulating compound 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]-thiophene (raloxifene).The present invention provides a process for preparing a class of compounds having the structure wherein: n is 0, 1, or 2; R is hydrogen or C1-C4 alkyl; X<1> is hydrogen, cyano, 4-hydroxybenzoyl, 4-halobenzoyl, or 4-(C1-C4 alkoxy)benzoyl; Y is NR<4>R<5>, 4-hydroxyphenyl, or 4-(C1-C4 alkoxy)phenyl; R<4> and R<5> are independently hydrogen or C1-C4 alkyl. The compounds are useful intermediates in the preparation of a class of compounds including the selective estrogen receptor modulating compound 6-hydroxy-2-(4-hydroxyphenyl)-3-Ae4-(2-piperidinoethoxy)benzoylUebenzoAeb Ue-thiophene (raloxifene).

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Discovery of 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene

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Process for the synthesis of benzo[b]thiophenes

The present invention is directed to a new process for the synthesis of 2-aryl benzo[b]thiophenes, and to novel intermediates therefor.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Antiestrogens. 2. Structure-Activity Studies in a Series of 3-Aroyl-2-arylbenzothiophene Derivatives Leading to <6-Hydroxy-2-(4-hydroxyphenyl)benzothien-3-yl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone Hydrochloride (LY156758), a Remarkably Effective Estrogen Antagonist with On…

In an effort to prepare nonsteroidal antiestrogens demonstrating greater antagonism and less intrinsic estrogenicity than those currently available, a series of 3-aroyl-2-arylbenzothiophene derivatives was synthesized.These compounds were prepared by Friedel-Crafts aroylation of appropriate O-protected 2-arylbenzothiophene nuclei with basic side-chain-bearing benzoyl chlorides followed by removal of the protective groups to provide the desired compounds containing both hydroxyl and basic side-chain functionality.A particularly useful method for the cleavage of aryl methoxy ethers without removal of (dialkylamino)ethoxy side chain functionality elsewhere in the molecule was found to be AlCl3/EtSH.The benzothiophene derivatives were tested for their ability to inhibit the growth-stimulating action of estradiol on the immature rat uterus.Seemingly minor changes in the side-chain amine moiety were found to have profound effects on the ability of the compounds to antagonize estradiol.Analogues having basic side chains containing cyclic (pyrrolidine, piperidine, and hexamethyleneamine) moieties were found to have less intrinsic estrogenicity and to antagonize estradiol action more completely than their noncyclic counterparts.The most effective antiestrogen in the series, compound 44, <6-hydroxy-2-(4-hydroxyphenyl)benzothien-3-yl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone, elicited a modest uterotropic activity that did not increase with increasing dose.In antagonism of estradiol, 44 exhibited a degree of inhibition surpassing that of tamoxifen at any dose tested.The new benzothiophene antiestrogen was also shown to have high affinity for rat uterine cycloplasmic estrogen receptor and to be an inhibitor of the growth of DMBA-induced rat mammary tumors.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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2-Phenylbenzo[b]thiophene-based antiestrogens with mammary tumor inhibiting activity

In this study we extended our studies on heterocyclic antiestrogens to 2-phenylbenzo[b]thiophenes which can be considered as isosteric to the 2- phenylindole system. We synthesized a number of 6-hydroxy-2-(4- hydroxyphenyl)benzo[b]thiophenes with carbamoyl and amino functions in the side chain at carbon-3 and analyzed their biological properties. The binding affinities for the estrogen receptor are mainly influenced by the chain length whereas the hormonal profile depends on the nature of the functional group. From this study 3-[10-(2,2,3,3,4,4,4,-heptafluorobutyl- methylcarbamoyl)decyl]-6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene (6e) emerged as an antiestrogen with all the characteristics of a pure antagonist. It did not stimulate gene expression in HeLa cells cotransfected with the expression vector for the human estrogen receptor HEGO and the luciferase reporter plasmid EREwtc luc nor did it show any estrogenic activity in the mouse uterus weight test. In the latter assay, it completely abrogated the stimulatory effect of estrone. Due to its antiestrogenic potency it strongly inhibited the growth of estrogen-sensitive human MCF-7 breast cancer cells with an IC50 value of 5 nM. These data suggest that an amide function is combination with the fluorination of the terminal carbon atoms is an appropriate modification to abolish the estrogenic action of the 2- phenylbenzothiophene system.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A new anti-tubulin agent containing the benzo[b]thiophene ring system

A new type of inhibitor of tubulin polymerization was discovered based on the 3-aroyl-2-arylbenzo[b]thiophene molecular skeleton. The lead compound in this series, 2-(4′-methoxyphenyl)-3-(3′,4′,5′-trimethoxybenzoyl)-6- methoxybenzo[b]thiophene 1, inhibited tubulin polymerization, caused an increase in the mitotic index of CA46 Burkitt lymphoma cells, and inhibited the growth of several human cancer cell lines.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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COMPOSITIONS AND METHODS FOR TREATING ESTROGEN-RELATED MEDICAL DISORDERS

Disclosed herein are methods for treatment of estrogen-related medical disorders. The methods of treatment may comprise administering to a subject in need of such treatment a composition comprising a therapeutically effective amount of at least one compound of formula (I) or a pharmaceutically acceptable salt thereof.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Discovery of ERD-308 as a Highly Potent Proteolysis Targeting Chimera (PROTAC) Degrader of Estrogen Receptor (ER)

The estrogen receptor (ER) is a validated target for the treatment of estrogen receptor-positive (ER+) breast cancer. Here, we describe the design, synthesis, and extensive structure-activity relationship (SAR) studies of small-molecule ERalpha degraders based on the proteolysis targeting chimeras (PROTAC) concept. Our efforts have resulted in the discovery of highly potent and effective PROTAC ER degraders, as exemplified by ERD-308 (32). ERD-308 achieves DC50 (concentration causing 50% of protein degradation) values of 0.17 and 0.43 nM in MCF-7 and T47D ER+ breast cancer cell lines, respectively, and induces >95% of ER degradation at concentrations as low as 5 nM in both cell lines. Significantly, ERD-308 induces more complete ER degradation than fulvestrant, the only approved selective ER degrader (SERD), and is more effective in inhibition of cell proliferation than fulvestrant in MCF-7 cells. Further optimization of ERD-308 may lead to a new therapy for advanced ER+ breast cancer.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Discovery of 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene

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Treatment of mammary cancer

Mammary cancers are inhibited by administration of a combination of two drugs. The first compound is 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, and the second compound is tamoxifen.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

New explortion of 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Formula: C16H14O2S, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 63675-74-1, name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene. In an article£¬Which mentioned a new discovery about 63675-74-1

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Substituted 2,3-aryl-benzothiophene compounds having estrogenic activity

The invention provides 2,3-aryl-benzothiophene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions including hyperlipidemia, and estrogen-dependent cancer.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem