Extracurricular laboratory:new discovery of Benzo[b]thiophen-5-ol

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Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst

A method for the hydroxylation of aryl and heteroaryl halides, promoted by a catalyst based on a biarylphosphine ligand tBuBrettPhos (L5) and its corresponding palladium precatalyst (1), is described. The reactions allow the cross-coupling of both potassium and cesium hydroxides with (hetero)aryl halides to afford a variety of phenols and hydroxylated heteroarenes in high to excellent yield.

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Benzothiophene – Wikipedia,
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Brief introduction of 130-03-0

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One-step synthesis of thioaurones

A rapid, one-step preparation of 2-(arylmethylidene)-1-benzothiophen-3-ones (thioaurones) using directed alpha-metallation, ring closure and aldol-type condensation is described. The reaction leads exclusively to the Z-isomer.

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More research is needed about C8H6OS

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Synthesis and studies on spectroscopic as well as electron donating properties of the two alkoxy benzo[b]thiophenes

Synthesis, characterization, steady state and time resolved, using time correlated single photon counting as well as laser flash photolysis techniques, spectroscopic investigations were made for two alkoxy benzo[b]thiophene molecules: 5-methoxy benzo[b]thiophene (5MBT) and 5-methoxymethyl benzo[b]thiophene (5MMBT). In both non-polar n-heptane (NH) and polar acetonitrile (ACN) solvents and at ambient temperature the electronic absorption spectra of these thiophenes exhibit different band systems whose assignments were made from the measurements of the steady state excitation polarization spectra. Steady state fluorescence spectra of these molecules in the different polarity solvents show the presence of non-specific interactions. From the redox properties of the benzothiophenes, measured by cyclic voltammetry, their electron donating properties were observed in the presence of the well-known electron acceptor 9cyanoanthracene (9CNA). Further, detailed studies by laser flash photolysis techniques show that ion-recombination mechanism predominates after the initial excitation of the acceptor moiety using the third harmonic of Nd:YAG laser. This recombination together with the external heavy atom effect (the donor containing ‘sulphur’ atom) appears to be responsible for the formation of the triplet of the monomeric acceptor 9CNA. From the steady state experiments it is shown that both in non-polar NH and highly polar ACN the quenching in the fluorescence emission of 9CNA in the presence of the benzothiophene donors is brought about primarily by the external heavy atom effect and in ACN, although the presence of the photoinduced ET reaction is confirmed, this process seems, from the observed bimolecular dynamic quenching rate, kq, to be significantly masked by the external heavy atom effect.

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More research is needed about 16587-47-6

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Thermolysis of Thiophenedicarboxylic Acid Anhydrides as a Route to Five-Membered Hetarynes

Flow vacuum thermolysis (FVT) of the anhydrides of thiophene-2,3- (5) and -3,4-dicarboxylic acid (6) and of thianaphthene-2,3-dicarboxylic acid (7) in the presence of thiophene, 1,3-cyclohexadiene, or benzene gave thianthrene (15a), presumably by aromatization of an intermadiate Diels-Alder adduct of the diene traps and the aryne 2,3-didehydrothiophene (8).A similar rationale explains the formation of dibenzothiophene from 7 and thiophene, the four monomethylthianaphthenes 22-25 from 5 and cyclopentadiene, 5,6-dimethylthianaphthene (15f) from 5 and 2,3-dimethylbutadiene, and a mixture of hydroxythianaphthenes (15d) from 5 and furan.The latter reaction also produces a mixture of isomeric cyclopentanothiophenes (19) which probably arise by decarbonylation of 15d.An FVT reaction of 5 with propyne as the trap gave a mixture of allenyl-(28) and propynylthiophenes 29 which probably arise by an ene reaction of the trap and the aryne 8.Decomposition of the anhydrides 5 and 6 in molten anthracene led only to Friedel-Crafts products such as thienylanthracenes 33 and quinones 34 from 5 and 39 and 40 from 6.The diene reactivity of thiophene 13a in the gas phase was demonstrated by the formation of naphthalene from its reaction with benzyne generated from the thermolysis of indanetrione and by the formation of indene from 13a plus cyclopentadiene.Possible, but improbable, interpretations of the FVT results without invoking a five-membered hetaryne intermediate are considered.

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More research is needed about C8H6OS

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Isomer-Specific Hydrogen Bonding as a Design Principle for Bidirectionally Quantitative and Redshifted Hemithioindigo Photoswitches

A new class of bidirectionally quantitative photoswitches based on the hemithioindigo (HTI) scaffold is reported. Incorporation of a pyrrole hydrogen-bond donor leads to a bathochromic shift allowing for quantitative bidirectional isomerization. Additionally, extending conjugation from the electron-rich pyrrole results in quantitative visible-light photoswitches, as well as photoswitches that isomerize with red and near-infrared light. The presence of the hydrogen bond leading to the observed redshift is supported by computational and spectroscopic evidence.

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Extended knowledge of 6386-80-7

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Studies on cognitive enhancing agents. III. Antiamnestic and antihypoxic activities of a series of 1-bicycloaryl-2-(omega-aminoalkoxy)ethanols

2-(2-Aminoethoxy)-1-hydroxyethyl derivatives of bicyclic arenes (naphthalene, thianaphthene, benzofuran, and indole) were prepared and screened for antiamnestic (AA) and antihypoxic (AH) activities which were evaluated by measuring the reversing potency in electroconvulsion-induced amnesia and the protective effect against hypoxia, respectively, in mice. Compound 3o, 1-(benzo[b]thiophen-5-yl)-2-(2-diethylaminoethoxy)ethanol, showed the best AA and AH activity profile, being superior to our prototype compound, 2-(2-dimethylaminoethoxy)-1-phenylethanol (1). Elongation of the ethylene linkage in the side chain of 3o to 3- and 4-carbon moieties brought about a significant decrease in AH activity. Compound 3o was further investigated for its protective effect against CO2-induced memory impairment and for acute toxicity in mice. It is ten-fold more potent than tacrine in the amnesia-reversal assay and is considerably less toxic than tacrine.

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New heteroaryl carbamates: Synthesis and biological screening in vitro and in mammalian cells of wild-type and mutant HIV-protease inhibitors

New heteroaryl HIV-protease inhibitors bearing a carbamoyl spacer were synthesized in few steps and high yield, from commercially available homochiral epoxides. Different substitution patterns were introduced onto a given isopropanoyl-sulfonamide core that can have either H or benzyl group. The in vitro inhibition activity against recombinant protease showed a general beneficial effect of both carbamoyl moiety and the benzyl group, ranging the IC50 values between 11 and 0.6 nM. In particular, benzofuryl and indolyl derivatives showed IC50 values among the best for such structurally simple inhibitors. Docking analysis allowed to identify the favorable situation of such derivatives in terms of number of interactions in the active site, supporting the experimental results. The inhibition activity was also confirmed in HEK293 mammalian cells and was maintained against protease mutants. Furthermore, the metabolic stability was comparable with that of the commercially available inhibitors.

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Benzothiophene – Wikipedia,
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Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model

FLT3 mutation is among the most common genetic mutations in acute myeloid leukemia (AML), which is also related with poor overall survival and refractory in AML patients. Recently, FLT3 inhibitors have been approved for AML therapy. Herein, a series of new compounds with pyrazole amine scaffold was discovered, which showed potent inhibitory activity against FLT3-ITD and significant selectivity against both FLT3-ITD and AML cells expressing FLT3-ITD. Compound 46, possessing the most promising cellular activity, blocked the autophosphorylation of FLT3 pathway in MV4-11 cell line. Furthermore, the apoptosis and downregulation of P-STAT5 were also observed in tumor cells extracted from the MV4-11 cell xenografts model upon compound 46 treatment. Compound 46 was also metabolically stable in vitro and suppressed tumor growth significantly in MV4-11 xenografts model in vivo. Compound 46 showed no toxicity to the viscera of mice and caused no decrease in body weight of mice. In conclusion, the results of this study could provide valuable insights into discovery of new FLT3 inhibitors, and compound 46 was worthy of further development as potential drug candidate to treat AML.

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Chemistry, like all the natural sciences, begins with the direct observation of nature¡ª in this case, of matter. category: benzothiophene, C9H8S. A document type is Patent, introducing its new discovery., category: benzothiophene

BENZOTHIOPHENE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME

The present invention relates to a compound represented by following general formula (I): wherein R1 and R2 are independently selected from a substituted or unsubstituted C4 to C30 arylamine group, a substituted or unsubstituted C4 to C40 carbazole group, a substituted or unsubstituted C4 to C40 benzothiophene group or a substituted or unsubstituted C4 to C40 benzofuran group; L is a bridging group, and selected from a single bond substituted C4 to C40 arylamine group, a substituted C4 to C40 carbazole group, a substituted C4 to C40 benzothiophene group, O atom, N atom or S atom; R3-R10 are independently selected from H atom, a C1-C20 aliphatic compound containing linear or branched alkanes, alkenes or alkynes or a C6-C30 aromatic group, or two adjacent groups linking to be a ring forming a naphthothiophene derivatives; m and n are selected from integers of 1 to 3, as well as the addition of m and n is larger than 0 but less than or equal to 3. Also, the present invention relates to organic electroluminescent devices using the compound represented by general formula (I), especially a hole transporting material, a hole injecting material or a main material of organic luminescent material used in an OLED device.

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22913-24-2, Name is Methyl benzo[b]thiophene-2-carboxylate, belongs to benzothiophene compound, is a common compound. Recommanded Product: 22913-24-2In an article, once mentioned the new application about 22913-24-2.

Synthesis of substituted dihydrobenzothiopyrans and dihydrobenzopyrans by cation-mediated cyclisation reactions

Treatment with acid of thiosalicylaldehyde- and salicylaldehyde-derived phenyl 3-phenyl-2-propenyl thioethers and ethers possessing latent oxonium ion functionality triggers simple or tandem cyclisation to give substituted dihydrobenzothiopyrans and dihydrobenzopyrans. Some derivatisation reactions of the products are described.

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