Month: August 2021

Chemical Properties and Facts of Methyl 5-aminobenzo[b]thiophene-2-carboxylate

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The solution-phase synthesis of two 1000-membered positional scanning libraries of distamycin A analogues is described enlisting acid/base liquid-liquid extractions for isolation and purification of all intermediates and final products. The results of their screening for functional activity (L1210 cytotoxic potency) and DNA binding affinity were compared with those derived from libraries containing the same compound members but prepared in a smaller 10-compound mixture format. The positional scanning libraries, which are substantially less demanding to prepare, allowed the accurate detection of the global observations and the clearly more potent activities, but more subtle discoveries and less distinguishable activities were not detected. This is a natural consequence of testing the larger 100-compound mixtures and the relative insensitivity of the assays to the contribution of any single, uniquely acting compound in the mixture. Thus, the disadvantages associated with the loss of some information contained within the library must be balanced against the advantages of the ease of library synthesis and judged in light of the library screening objectives. Copyright (C) 2000 Elsevier Science Ltd.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

More research is needed about 5-Bromobenzothiophene

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For the first time, an approach to 3,4-disubstituted thietes was developed through two complementary paths. While the first one relies on alpha-metalation, the second is based on direct C-H functionalization. A new library of sophisticated sulfur-containing four-membered rings is described, paving the way to new bioactive analogues and small heterocycle incorporation.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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The invention discloses a [1 – [2 – methyl – 3 – benzothienyl], 2 – (2 – methyl – 5 – (4 – phenyl) – (2 – formyl quinoline – 8 – benzothiazolyl) – 3 – thienyl)] full-PVC pentene and its preparation method and application. Preparation method: to benzo thiophene as raw materials, through the iodomethane substituted, brominated, with the perfluoro pentene reaction to generate single substituted perfluoro pentene; to 2 – methyl thiophene as raw materials, bromination, through the n-BuLi and tributyl borate reaction, Stuzki coupling reaction through the end of the with the thiophene ring containing aldehyde group benzene connected, then with ethylene glycol protection after single substituted perfluoro pentene reaction, by reducing dioxiding hydroxy, any change of containing methyl radical bromine, with 8 – hydroxy quinoline – 2 – aldehyde reaction, finally with 2 – amino thiophenol reaction, to obtain the target compound. Prepared by the invention compounds can be used for continuous detection of a specific ion and amino acid, its selectivity is very good. (by machine translation)

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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

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The title compound 5 is synthesized by the reaction of the potassium salt of 3-aminobenzothiophene-2-carboxylic acid with phosgene.Compound 5 is readily alkylated to give 6 with methyl iodide, benzyl bromide, or propargyl bromide in the presence of sodium hydride.Reaction of 5 and 6 with nucleophiles follows specifically different pathways.Compound 5 is readily ionized to the isocyanate species 13 and subsequently reacts with methanol or methylamine to produce exclusively the carbamate 7 or ureido acid 9.The N-substituted derivative 6, in analogous reaction withmethanol or methylamine, produce exclusively the amino ester 8 or the amino amide 10.The N-benzyl derivative 6b reacts with the cyclic S-methylthiopseudourea 11 to give the tetracycle 12, a new ring system.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Top Picks: new discover of C8H5BrS

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A highly efficient method of visible light mediated Ni(II)-catalyzed photoredox N-arylation of Cbz-amines/Boc-amines with aryl electrophiles at room temperature is reported. The methodology provides a common access to a wide variety of N-aromatic and N-heteroaromatic carbamate products that find use in the synthesis of several biologically active molecules and provides a distinct advantage over traditional palladium-catalyzed Buchwald reaction.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Our Top Choice Compound: C8H6OS

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Heating acetoxybenzothiophens with AlCl3-benzene can give the normal Fries-rearranged products (for the 4-OAc and 7-OAc isomers); these sometimes react further to give their 2,3-dihydro- (for 4-OAc and 7-OAc) or 2-phenyl derivatives (for 6-OAc).Alternatively, benzene can add across the 2,3-double bond of the acetoxy-compound, to give the 2- (for 6-OAc) or 3-phenyl-2,3-dihydrobenzothiophens (for 7-Oac).With AlCl3 in dichloromethane, 6-acetoxybenzothiophen undergoes intermolecular transfer of an acetyl group to give a mixture of 6-acetoxy-2- and 3-acetylbenzothiophens and 6-hydroxybenzothiophen.With AlCl3 in benzene at room temperature, 4-acetoxybenzothiophen gives a rearranged product, 4,5-dihydro-2,4-diphenylbenzothiophen-7(6H)-one (3a) (17percent).In the presence of AlCl3 for 0.5 h, 4-, 5-, 6-, and 7-hydroxybenzothiophens undergo addition of benzene or toluene, to give the appropriate 2-aryl-2,3-dihydrohydroxybenzothiophens (1).Yields are high for the 4- and 6-hydroxy-isomers (80-85percent), but lower for the 5- (55percent) and 7-isomers (10percent).In each of these reactions the starting hydroxybenzothiophen is partly converted into its 2,3-dihydro-derivative. 5- and 7-Hydroxybenzothiophen also each give the same 4,5-dihydro-2,4-diarylbenzothiophen-7(6H)-one (3) (25percent) in this reaction.When the reaction period with benzene or toluene is extended to 5 days, the amount of solvent addition product (1) decreases, but all four hydroxy-isomers now give the same rearranged product (3).The mechanism of this unusual rearrangement is discussed in terms of a spiro-intermediate.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Archives for Chemistry Experiments of Methyl 6-bromobenzo[b]thiophene-2-carboxylate

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In order to explore novel tau-imaging agents that can selectively detect neurofibrillary tangles in Alzheimers disease (AD) brains, we designed and synthesized a series of heterocyclic phenylethenyl and (3-pyridinyl)ethenyl derivatives with or without a dimethyl amino group. In in vitro autoradiography using AD brain sections, all radioiodinated ligands with a dimethyl amino group bound to Abeta deposits in the sections. In contrast, the ligands without a dimethyl amino group showed different patterns of radioactivity accumulation in the sections depending on the kind of heterocycle contained in their molecules. Particularly, a phenylethenyl benzimidazole derivative ([125I]64) showed marked radioactivity accumulation in the temporal lobe which corresponded with the distribution of tau deposits. [125I]64 also showed the most favorable pharmacokinetics in normal mouse brains (3.69 and 0.06% ID/g at 2 and 60 min postinjection, respectively) among all ligands in this study. Taken together, these results suggest that [123I]64 may be a new candidate tau-imaging agent.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Extended knowledge of C10H8O2S

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A series of 4-substituted (benzo[b]thiophene-2-carbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardioprotective efficacy both in vitro and in vivo. Several analogs exhibited a strong inhibition on NHE-1, and which was generally well correlated with their cardioprotective efficacy. Especially the 4-nitro 20 and cyano 50 compounds excellently improved the cardiac function and reduced infarct size against ischemia/reperfusion injury.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Can You Really Do Chemisty Experiments About 19301-35-0

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This work focuses on the development of specific substrates for estrogen sulfotransferase (SULT1E1) to produce molecular imaging probes for this enzyme. SULT1E1 is a key enzyme in estrogen homeostasis, playing a central role in the prevention and development of human disease. In vitro sulfation assays showed alkyl and aryl substitutions to a fused heterocyclic system modeled after beta-naphthol (betaN), based on compounds that interact with the estrogen receptor, rendered several molecules with enhanced specificity for SULT1E1 over SULT1A1*1, SULT1A1*2, SULT1A3, and SULT2A1. Several 6-hydroxy-2-arylbenzothiazoles tested demonstrated excellent affinity – V max/Km ratios – and specificity for SULT1E1. Km values ranged from 0.12-2.36 muM. A strong correlation was observed between polarity of the 4?-sustituent on the 2-aryl moiety (Hammett sigmap) and the log(Vmax/Km) (r = 0.964). Substrate sensitivity is influenced by the acidity of the 6-phenolic group demonstrated by correlating its 1H NMR chemical shift (deltaOH) with the log(V max/Km) (r = 0.963). Acidity is mediated by the electron withdrawing capacity of the 4?-substituent outlined by the correlation of the C-2 13C NMR chemical shift (deltaC2) with the log(Vmax/Km) (r = 0.987). 2-[4-(Methylamino)phenyl]-6- hydroxybenzothiazole (2b) was radiolabeled with carbon-11 (11C-(2b)) and used in vivo for microPET scanning and tissue metabolite identification. High PET signal was paralleled with the presence of radiolabeled 11C-(2b)-6-O-sulfate and the SULT1E1 protein detected by western blot. Because this and other members of this family presenting specificity for SULT1E1 can be labeled with carbon-11 or fluorine-18, in vivo assays of SULT1E1 functional activity are now feasible in humans.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

More research is needed about Methyl 3-aminobenzo[b]thiophene-2-carboxylate

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For an organic compound represented by formula 1, organic optoelectronic device and the display device are disclosed. [Formula 1] In said formula 1, Ar1 , Ar2 , L1 , L2 , R1 To R3 Efined specification is based on. (by machine translation)

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem