Extracurricular laboratory:new discovery of Methyl 3-aminobenzo[b]thiophene-2-carboxylate

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Syntheses of substituted 2,4-dioxo-thienopyrimidin-1-acetic acids and their evaluation as aldose reductase inhibitors

A series of 2,4-dioxo-thieno[2,3-d], [3,2-d] and [3,4-d]pyrimidin-1-acetic acids (2) with a benzyl moiety at the N-3 position were prepared and tested in vitro for aldose reductase inhibitory activity against partially purified enzyme from rat lens. Some of these compounds were also evaluated for inhibition of sorbitol accumulation in the sciatic nerve or lens of streptozotocin-induced diabetic rats in vivo. Among the synthesized compounds, several showed potent aldose reductase inhibitory activity with IC50s in the 10-8 M range. Particularly, the potencies of non-substituted thieno- (2a and 2aa), 5-methylthieno- (2c), 5,6-dimethylthieno- (2g), 6-isopropylthieno- (2j and 2k), 6-chlorothienopyrimidine (2q) and benzothienopyrimidine (2ac) analogs were approximately equipotent ot FK-366 (1A) and Ponalrestat (1B) as references. Although most compounds were inactive in vivo, 2 compounds, 2k and 2q, possessed moderate in vivo activity.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example

Phosphodiesterase (PDE) 7 is a high affinity cAMP-specific PDE whose functional role in T-cells has been the subject of some controversy. Recent findings on tissue distribution, however, support the hypothesis that PDE7 could be a good target for the treatment of airway diseases, T-cell related diseases or central nervous system (CNS) disorders. Therefore, the identification of selective inhibitors targeted against PDE7 enzyme has become an attractive area of research. We report here the first use of the descriptors generated by the CODES program for ligand-based virtual screening. This program codifies molecules from a topological point of view and the generated descriptors are related to the chemical nature of the atoms, the atomic bonds and the connectivity with the rest of the molecule. They are also able to distinguish among stereoisomers. By using this approach, 173 compounds were codified, and their similarity with the reference compound was analysed. Based on the analysis, new potential PDE7 inhibitors have been identified, synthesized and biologically evaluated confirming that CODES descriptors are valid for ligand-based virtual screening and provided new lead compounds for further optimization as potent and selective PDE7 inhibitors.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

The Absolute Best Science Experiment for 5-Bromobenzothiophene

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Regiospecific alkyl addition of (hetero)arene-fused thiophenes enabled by a visible-light-mediated photocatalytic desulfuration approach

A photoredox-mediated, regiospecific alkyl addition reaction of (hetero)arene-fused thiophenes has been developed, employing bench-stable N-benzoyl alkyl-sulfinamides as the alkyl sources. This protocol offers a unique desulfuration approach to generate alkyl radicals that proceeds via nitrogen-centered radical intermediates.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Electric Literature of 5394-13-8, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.5394-13-8, Name is 2-Bromobenzo[b]thiophene, molecular formula is C8H5BrS. In a Article£¬once mentioned of 5394-13-8

Addition Reactions of Benzothiophen. Part 3. Addition and Ring-opening Reactions with Phenolic Ethers

In the presence of aluminium chloride, anisole, phenetole, diphenyl ether, and (methylthio)benzene are added rapidly across the 2,3-bond in benzothiophen to give, inter alia, a mixture of 2- and 3-(p-substituted aryl)-2,3-dihydrobenzothiophens (3) and (4).Contrary to expectation, the 2-isomer predominates in all cases, and the addition is irreversible.Reaction with anisole also leads to a novel ring-opened product, viz. (E)-4-methoxy-2′-methylthiostilbene (9a), which was synthesised unambigiuously.It is believed that benzothiophen is S-methylated by PhOMe-AlCl3 in a ‘push-pull’ reaction, and that the resulting positive charge is delocalised into the ring, thus allowing the 2-position to participate in electrophilic attack on a second molecule of anisole.The resulting quadrivalent sulphur intermediate achieves stabilisation by means of a rapid ring-opening reaction.Other aromatic methyl ethers give analogous products, but phenetole diphenyl ether, and (methylthio)benzene do not promote ring-opening.The ring-opening reaction is aided by the addition of MeBr- or EtBr-AlCl3; even phenetole will then undergo ring-opening.Under these conditions the S-alkyl group in the ring-opened product comes from the starting ether, and not from the added MeBr or EtBr.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Archives for Chemistry Experiments of Methyl benzo[b]thiophene-2-carboxylate

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Ru-Catalyzed Selective C(sp3)?H Monoborylation of Amides and Esters

A ruthenium-catalyzed method has been developed for the C(sp3)?H monoborylation of various unactivated alkyl and aryl amides and challenging esters, with a low-cost and bench-stable boron source, providing boronates with exclusive selectivity, high efficiency, and high turnover number (up to 8900). This novel strategy may offer a versatile and environmentally friendly alternative to current methods for selective C(sp3)?H borylation that employ even more expensive metals, such as iridium and rhodium.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthetic Route of 5394-13-8, 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.5394-13-8, Name is 2-Bromobenzo[b]thiophene, molecular formula is C8H5BrS. In a article£¬once mentioned of 5394-13-8

A new synthetic approach to 6-unsubstituted phenanthridine and phenanthridine-like compounds under mild and metal-free conditions

A new and mild synthetic approach for the synthesis of 6-unsubstituted phenanthridine and phenanthridine-like compounds under metal-free conditions at room temperature has been developed. The strategy involved a tandem azide rearrangement/intramolecular annulation and oxidation reactions of biarylmethyl azide precursors to obtain the desired products in up to 99% yields with high regioselectivity.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Discovery of 2-Bromobenzo[b]thiophene

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Application of 5394-13-8, 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.5394-13-8, Name is 2-Bromobenzo[b]thiophene, molecular formula is C8H5BrS. In a article£¬once mentioned of 5394-13-8

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF

Discloses a novel compound capable of improving the luminous efficiency, stability and lifetime of an element, and an organic electronic element. or an electronic device using the same. (by machine translation)

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

A new application about 5-Bromobenzothiophene

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Reference of 4923-87-9, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 4923-87-9, molcular formula is C8H5BrS, introducing its new discovery.

Identification of fused-ring alkanoic acids with improved pharmacokinetic profiles that Act as G protein-coupled receptor 40/free fatty acid receptor 1 agonists

The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2?,6?-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl} propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to beta-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4?-(2-ethoxyethoxy)-2?,6?-dimethylbiphenyl-3-yl]methoxy} -2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Electric Literature of 20503-40-6, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 20503-40-6, molcular formula is C8H7NO2S, introducing its new discovery.

COVALENT IRREVERSIBLE INHIBITORS OF USP7 AS ANTI-CANCER AGENTS

Compounds and pharmaceutical compositions for treating cancer by, for example, modulating immune system activity, are provided.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Final Thoughts on Chemistry for 5-Bromobenzothiophene

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Nickel-catalyzed difunctionalization of unactivated alkenes initiated by unstabilized enolates

This report demonstrates the possibility of a nickel-catalyzed difunctionalization of unactivated alkenes initiated by an unstabilized enolate nucleophile. The process tolerates a diverse range of electrophiles, including aryl, heteroaryl, alkenyl, and amino electrophiles. An electron-deficient phosphine ligand and a tetrabutylammonium salt additive were crucial for promoting efficient vicinal difunctionalization.

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