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SUBSTITUTED BENZO(B)THIOPHENE COMPOUNDS HAVING ACTIVITY AS SELECTIVE ESTROGEN RECEPTOR MODULATORS

The present invention provides compounds with nitrogen, sulfur or carbon linked basic side chains of formula STR1 where R 1 and R. sup.2 are independently hydrogen, halo, hydroxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy, arylcarbonyloxy, aryloxycarbonyloxy, or alkylsulfonyloxy; O–SO 2–(C 4-C 6 alkyl), chloro, fluoro, or bromo; W is CHOH, C(O), or CH 2 ; Y is–CH 2–,–NH–,–NMe–,–S–,–SO 2–; and R 3 and R. sup.4 are independently hydrogen, alkyl, alkylcarbonyl, alkylamino-carbonyl, or arylcarbonyl, or together with the nitrogen to which they are attached form 1-pyrrolidinyl, 1-piperidinyl, or a 5-or 6-membered imide or cyclic amide ring.

The present invention also provides pharmaceutical compositions containing the compounds optionally containing estrogen or progestin, and the use of such compounds, alone, or in combination with estrogen or progestin, for treating osteoporosis, aortal smooth muscle cell proliferation, (particularly restenosis), and estrogen-dependent cancer (particularly breast cancer).

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A Chimeric SERM-histone deacetylase inhibitor approach to breast cancer therapy

Breast cancer remains a significant cause of death in women, and few therapeutic options exist for estrogen receptor negative (ER (-)) cancers. Epigenetic reactivation of target genes using histone deacetylase (HDAC) inhibitors has been proposed in ER (-) cancers to resensitize to therapy using selective estrogen receptor modulators (SERMs) that are effective in ER (+) cancer treatment. Based upon preliminary studies in ER (+) and ER (-) breast cancer cells treated with combinations of HDAC inhibitors and SERMs, hybrid drugs, termed SERMostats, were designed with computational guidance. Assay for inhibition of four typea I HDAC isoforms and antagonism of estrogenic activity in two cell lines yielded a SERMostat with 1-3a muM potency across all targets. The superior hybrid caused significant cell death in ER (-) human breast cancer cells and elicited cell death at the same concentration as the parent SERM in combination treatment and at an earlier time point.

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Reference：
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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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Related Products of 63675-74-1, Chemistry is the experimental science by definition. We want to make observations to prove hypothesis. For this purpose, we perform experiments in the lab. 63675-74-1, Name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene,introducing its new discovery.

Benzothiophene compounds, intermediates, compositions, and methods

The present invention provides intermediate compounds and processes for the preparation of compounds of formula I STR1 wherein R1a is –H or –OR7a in which R7a is –H or a hydroxy protecting group; R2a is –H, halo, or –OR8a in which R8a is –H or a hydroxy protecting group; R3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; n is 2 or 3; and Z is –O– or –S–; or a pharmaceutically acceptable salt thereof.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A PROCESS FOR PREPARING BENZO[B]THIOPHENE DERIVATIVES

The present invention relates in general to the field of organic chemistry, and in particular to the preparation of benzo[b]thiophene derivatives. These benzo[b]thiophene derivatives are useful as intermediates in the synthesis of pharmaceutically active agents such as raloxifene or derivatives thereof.

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Benzothiophene – Wikipedia,
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Electric Literature of 63675-74-1, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.63675-74-1, Name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene, molecular formula is C16H14O2S. In a article，once mentioned of 63675-74-1

Novel nonsteroidal selective estrogen receptor modulators. Carbon and heteroatom replacement of oxygen in the ethoxypiperidine region of raloxifene

Compounds were synthesized where oxygen in the ethoxypiperidine region of raloxifene is replaced with carbon, sulfur, or nitrogen linkages. Thia- and aza-substituted compounds were prepared by novel methodology. The compounds were evaluated in vitro as selective estrogen receptor modulators (SERMs). Calculations suggested the compounds exhibit an ER-alpha binding affinity/conformational energy relationship.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Application of 63675-74-1, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.63675-74-1, Name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene, molecular formula is C16H14O2S. In a article，once mentioned of 63675-74-1

Estrogen receptors (ERs) play a major role in the growth of human breast cancer cells. A selective estrogen receptor down-regulator (SERD) that acts as not only an inhibitor of ligand binding, but also induces the down-regulation of ER, would be useful for the treatment for ER-positive breast cancer. We previously reported that tamoxifen derivatives, which have a long alkyl chain, had the ability to down-regulate ERalpha. With the aim of expanding range of the currently available SERDs, we designed and synthesized raloxifene derivatives, which had various lengths of the long alkyl chains, and evaluated their SERD activities. All compounds were able to bind ERalpha, and RC10, which has a decyl group on the amine moiety of raloxifene, was shown to be the most potent compound. Our findings suggest that the ligand core was replaceable, and that the alkyl length was important for controlling SERD activity. Moreover, RC10 showed antagonistic activity and its potency was superior to that of 4,4?-(heptane-4,4-diyl)bis(2-methylphenol) (18), a competitive antagonist of ER without SERD activity. These results provide information that will be useful for the development of promising SERDs candidates.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Cycloisomerization of homopropargylic thiols to dihydrothiophenes is promoted by group VI metal carbonyls. Related thiacyclization transformations under basic and radical conditions are also described, including regioselective formation of benzothiophenes from aryl methyl sulfides and alkynes.

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Benzothiophene – Wikipedia,
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Electric Literature of 63675-74-1, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.63675-74-1, Name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene, molecular formula is C16H14O2S. In a Patent，once mentioned of 63675-74-1

TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS WITH SELECTIVE ESTROGEN RECEPTOR MODULATORS

The present invention provides a method of treating depression, mood swings, or Alzheimer’s disease in a patient in need of such treatment by administering a selective estrogen receptor modulating compound of the formula STR1 in which R 1 and R 2 are independently hydroxy and alkoxy of one to four carbon atoms; and R 3 and R 4 are independently methyl or ethyl, or R 3 and R 4, taken together with the nitrogen atom to which they are attached, form a pyrrolidino, methyl-pyrrolidino, dimethylpyrrolidino, piperidino, morpholino, or hexamethyleneimino ring.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Synthetic Route of 63675-74-1, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.63675-74-1, Name is 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene, molecular formula is C16H14O2S. In a Patent，once mentioned of 63675-74-1

Process for preparing benzoic acids

An improved process for the preparation of 4[(2-piperidin-1-yl)ethoxy]benzoic acid derivatives, comprising reacting a haloalkyl amine of formula (III) with a compound of formula (IV) in the presence of a hydrated inorganic base in an appropriate solvent.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem