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INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION AND ANXIETY

The present invention provides compounds of formula (I): which are useful for treating depression, anxiety, and alleviating the symptoms caused by withdrawal or partial withdrawal from the use of tobacco or of nicotine.

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Benzothiophene – Wikipedia,
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Application of directed metalation in synthesis. Part 4: Expedient synthesis of substituted benzo[b]thiophene and naphthothiophene

A short, simple and inexpensive synthesis of several diversely substituted benzo[b]thiophenes and one naphthothiophene is described. The method involves introduction of methylsulfanyl group ortho- to the amide function of readily available N,N-diethylamides of aryl carboxylic acid by directed metalation. Thioindoxyls, obtained in high yields through side-chain deprotonation and cyclisation in one pot, are reduced to benzo[b]thiophene or napthothiophene.

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Chromatographic studies of purity and segregation behaviour of natural impurities present in coal tar acenaphthene and pyrene

Twenty one (two unidentified) and 14 impurities were detected and identified in the bottom parts of the zone refined ingots of commercially available ex-coal tar acenaphthene and pyrene, respectively, with the help of Hewlett-Packard gas chromatographs type 6890 GC System and 5890 series II equipped with fused silica capillary columns and the FID and MS detectors. The result of quantitative determination have shown that naphthalene, 2-methylnaphthalene and 9H-fluorene, and 7-methylanthracene, 1-phenylnaphthalene, fluoranthene and unknown compound with the molecular weight of 208 may be treated as the major impurities of the above hydrocarbons, respectively. These results have also shown that with the exception of methyldibenzofuran present as impurity in acenaphthene, the segregation coefficients of all the remaining detected impurities are lower than unity. Moreover, it was found that the final distribution of the major impurities after 100 passes of the melting zone may be described with high accuracy by a third-order equation. The purification procedure worked out on the basis of the determined impurity segregation behaviour enabled the preparation of the hydrocarbons with purity ?99.999mass% from which high quality crystals were grown.

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Benzothiophene – Wikipedia,
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Heterocyclic thromboxane synthetase inhibitors and pharmaceutical compositions containing them

Heterocyclic thromboxane synthetase inhibitors of the formula STR1 wherein R1, which is attached to the 2-, 3- or 4-position, is hydrogen, halogen, C1 -C4 alkyl, hydroxy or C1 -C4 alkoxy; Y, which is attached to the 2- or 3-position, is –COOH, –COO(C1 -C4 alkyl) or –CONH2 ; X is O, S, NH, N(C1 -C4 alkyl) or N(benzyl); and R, which is attached to the 5-, 6- or 7-position, is a group of the formula STR2 or (3- or 4-pyridyl)-Z2 – wherein Z1 is –CH2 –, –CH2 CH2 — or –CH2 CH2 O– and Z2 is –CH2 –, –CH2 CH2 –, –CH=CH–, –CH2 O– or –OCH2 –; and their pharmaceutically acceptable salts; processes for their preparation, and pharmaceutical compositions containing them.

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Sulfur from benzothiophene and alkylbenzothiophenes supports growth of Rhodococcus sp. strain JVH1

Rhodococcus sp. strain JVH1 was previously reported to use a number of compounds with aliphatic sulfide bridges as sulfur sources for growth. We have shown that although JVH1 does not use the three-ring thiophenic sulfur compound dibenzothiophene, this strain can use the two-ring compound benzothiophene as its sole sulfur source, resulting in growth of the culture and loss of benzothiophene. Addition of inorganic sulfate to the medium reduced the conversion of benzothiophene, indicating that benzothiophene metabolism is repressed by sulfate and that benzothiophene is therefore used specifically as a sulfur source. JVH1 also used all six isomers of methylbenzothiophene and two dimethylbenzothiophene isomers as sulfur sources for growth. Metabolites identified from benzothiophene and some methylbenzothiophenes were consistent with published pathways for benzothiophene biodesulfurization. Products retaining the sulfur atom were sulfones and sultines, the sultines being formed from phenolic sulfinates under acidic extraction conditions. With 2-methylbenzothiophene, the final desulfurized product was 2-methylbenzofuran, formed by dehydration of 3-(o-hydroxyphenyl) propanone under acidic extraction conditions and indicating an oxygenative desulfination reaction. With 3-methylbenzothiophene, the final desulfurized product was 2-isopropenylphenol, indicating a hydrolytic desulfination reaction. JVH1 is the first microorganism reported to use all six isomers of methylbenzothiophene, as well as some dimethylbenzothiophene isomers, as sole sulfur sources. JVH1 therefore possesses broader sulfur extraction abilities than previously reported, including not only sulfidic compounds but also some thiophenic species.

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Degradation of the petroleum component’s monomethylbenzothiophenes on exposure to light

The photochemical degradation of monomethylated benzo[b]thiophenes in aqueous solution was studied to elucidate the fate of crude oil components after an oil spill. One principal reaction pathway involves oxidation of the methyl group(s) to the carboxylic acids via aldehydes. Another pathway leads via oxidation of the thiophene ring to the quinone and then, after ring opening, to 2-sulfobenzoic acids as the ultimate products for all compounds. Opening of the benzo ring is also seen in which case thiophene aldehydes or ketones are formed.

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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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ALKYLATION OF THIOPHENES AND PREPARATION OF BENZOTHIOPHENES USING MODIFIED MONTMORILLONITE CLAY CATALYSTS

Regioselective benzylation of thiophene and benzothiophene using benzyl chloride and a ZnCl2-promoted montmorillonite catalysts is described.An improved process for the cyclization of (arylthio)acetaldehyde dialkyl acetals to benzothiophenes using the same catalyst is also documented.

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Advances toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 1

A series of 1-aryloxy-3-piperidinylpropan-2-ols possessing potent dual 5-HT1A receptor antagonism and serotonin reuptake inhibition was discovered. 1-(1H-Indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols exhibited selective and high affinity at the 5-HT1A receptor and serotonin reuptake inhibition at nanomolar concentrations for dual activities.

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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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