Discovery of 4-Methylbenzo[b]thiophene

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Bacterial transformations of benzothiophene and methylbenzothiophenes

The abilities of three Pseudomonas strains to transform each of the six isomers of methylbenzothiophene was studied. These compounds would not support growth but were biotransformed in a cell suspension of one of the isolates and in cultures of the other two isolates while they grew on 1- methylnaphthalene or glucose. Sulfur-containing metabolites were identified by GC/MS and GC/FTIR, and when possible, by comparison with authentic standards. Sulfoxides and sulfones were frequently detected and were the most abundant products from 2- and 3-methylbenzothiophene. Two of the isolates oxidized the methyl groups to carboxylic acids which were abundant products from 3-, 5-, and 6-methylbenzothiophenes. Benzothiophenemethanols were often detected, but in very low amounts. 2,3-Diones were observed as metabolites of benzothiophene and those methylbenzothiophenes with a methyl group on the benzene ring. Isomers of tolyl methyl sulfoxide were observed as ring cleavage products from 6- and 7-methylbenzothiophene.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthesis and Structure-Activity Relationship of Benzothienylallylamine Antimycotics

Benzothiophene analogues of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied.Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2.Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzothienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far.In general, substituted benzothiophenes can be used not only as potential equivalents of naphthalene in bioactive compoudns but also as a tool to selectively modify biological activities.

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Benzothiophene | C8H6S – PubChem

 

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An improved synthesis of substituted benzo[b]thiophenes using microwave irradiation

An easy and high-yielding method for the synthesis of substituted benzo[b]thiophenes using microwave irradiation is described.

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Oxidation mechanism of dibenzothiophene compounds: A computational study

The potential energy surfaces of the oxidation of three model heterocyclic organic sulfides dibenzothiophene (DBT), 4-methylbenzothiophene (MDBT) and 4,6-dimethyldibenzothiophene (2MDBT) were examined using HCO3H as oxidants adopting MP2, omegaB97X-D, M06-2X and B3LYP methods at 6-311+G (d,p) level. The stationary points on the potential energy surfaces for the first and second oxidation reaction were fully optimized and characterized. The natural orbital population analysis (NPA) was also performed to understand the charge distribution. The calculated results may contribute to understanding the reaction mechanism of the ODS of refractory DBT sulfides.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A liquid chromatography?atmospheric pressure photoionization tandem mass spectrometric method for the determination of organosulfur compounds in petroleum asphalt cements

We present a sensitive liquid chromatography?atmospheric pressure photoionization tandem mass spectrometric (UHPLC-APPI-MS/MS) method for the determination of selected organosulfur compounds in Brazilian asphalt cements. It was possible to detect 14 organosulfur compounds of different classes where sulfoxides and sulfones presented higher sensibility in ionization than thiophenes and aromatic sulfides. A dopant-assisted APPI method was also tested, however, when chromatographic flow rate was optimized a decrease in signal was observed for all compounds. PAHs were tested and ruled out as possible interfering compounds and the matrix effect of asphalt cements was within an acceptable range for the quantification of organosulfur compounds. The proposed method was found to have satisfactory linearity and accuracy with recoveries between 83.85 and 110.28% for thianaphthene and 3-methylbenzothiophene, respectively. Therefore, the method allowed the characterization of organosulfur compounds in Brazilian asphalt cements and demonstrated changes in the amount quantified in asphaltenic and maltenic fractions after the RTFOT?+?SUNTEST aging process.

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Benzothiophene – Wikipedia,
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POLYNUCLEOTIDE CONSTRUCTS HAVING DISULFIDE GROUPS

The invention features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains one or more bulky groups proximal to the disulfide group. The invention also features polynucleotide constructs containing one or more components (i) containing a disulfide linkage, where each of the one or more components (i) is attached to an internudeotide bridging group or a terminal group of the polynucleotide construct, and each of the one or more components (i) contains at least 4 atoms in a chain between the disulfide linkage and the phosphorus atom of the internudeotide bridging group or the terminal group; and where the chain does not contain a phosphate, an amide, an ester, or an alkenylene. The invention also features methods of delivering a polynucleotide to a cell using the polynucleotide constructs of the invention.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A method for measuring 1-octanol-water partition coefficients.

A new direct method to determine the 1-octanol-water partition coefficients (Kow, expressed as log Kow) was tested. A dialysis tubing was used to separate water from the octanol phase containing the analyte (naphthalene, aniline, benzo(b)thiopene, etc.), avoiding the frequently encountered problem of emulsions. Different tubings with molecular weight cutoffs of 2000-12,000 mol wt were equally suitable. The analyte concentrations were determined by LC, allowing compounds to be measured in impure samples. The correlation coefficient was 0.998 for log Kow between experimental and theoretical data. The method quickly determines log Kow without a great hardware expense. A >90% savings in equilibration time can be easily achieved by using ultrasonic agitation. The method is experimentally straightforward.

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Some scientific research about 4-Methylbenzo[b]thiophene

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Abiotic oxidation of petroleum bitumens under natural conditions

Five series of crude oil samples exposed to atmospheric conditions have been analysed at the molecular level, each series comprising several samples originating from the same crude oil but altered to different extents. The aim of our investigation was to compare the specific impact of abiotic oxidation to other alteration processes such as biodegradation, evaporation and water washing. Bulk analyses revealed that increasing alteration is accompanied by an increase in oxygen content which parallels a relative increase of the proportions, as well as of the molecular weights of the macromolecular constituents of the bitumens. Gas chromatographic-mass spectrometric analyses of polar fractions showed the presence of oxygen-containing compounds (steroid ketones, benzothiophenic acids and sulfones) which result from oxidation of petroleum lipids. The hypothesis that part of these oxygenated compounds results from abiotic oxidation processes rather than from biodegradation is supported, notably, by the fact that oxygen incorporation generally occurred without any diastereomeric discrimination. This is also supported by simulation experiments performed on petroleum lipids, which showed that abiotic oxidation induces cleavage reactions affecting C-C and C-S bonds which may intervene in the transformation of geomacromolecules in the environment by degradation (‘depolymerization’). Thus abiotic oxidation may play a major role in the fate of petroleum pollutants in the environment by transforming lipidic organic matter from petroleum into more water soluble and, therefore, more biodegradable constituents. However, these can be more toxic to the environment as the water-soluble fraction may be easily taken up by biota. (C) 2000 Elsevier Science Ltd. Five series of crude oil samples exposed to atmospheric conditions have been analyzed at the molecular level, each series comprising several samples originating from the same crude oil but altered to different extents. The aim of our investigation was to compare the specific impact of abiotic oxidation to other alteration processes such as biodegradation, evaporation and water washing. Bulk analyses revealed that increasing alteration is accompanied by an increase in oxygen content which parallels a relative increase of the proportions, as well as of the molecular weights of the macromolecular constituents of the bitumens. Gas chromatographic-mass spectrometric analyses of polar fractions showed the presence of oxygen-containing compounds (steroid ketones, benzothiophenic acids and sulfones) which result from oxidation of petroleum lipids. The hypothesis that part of these oxygenated compounds results from abiotic oxidation processes rather than from biodegradation is supported, notably, by the fact that oxygen incorporation generally occurred without any diastereomeric discrimination. This is also supported by simulation experiments performed on petroleum lipids, which showed that abiotic oxidation induces cleavage reactions affecting C-C and C-S bonds which may intervene in the transformation of geomacromolecules in the environment by degradation (`depolymerization’). Thus abiotic oxidation may play a major role in the fate of petroleum pollutants in the environment by transforming lipidic organic matter from petroleum into more water soluble and, therefore, more biodegradable constituents. However, these can be more toxic to the environment as the water-soluble fraction may be easily taken up by biota.

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Benzothiophene – Wikipedia,
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Dihydroimidazo[2,1-b]thiazole and dihydro-5h-thiazolo[3,2-A]pyrimidines as antidepressant agents

The present invention relates to certain novel substituted dihydroimidazo[2,1-b]thiazole and dihydro-5H-thiazolo[3,2-a]pyrimidine compounds of Formula (I) including pharmaceutically acceptable salts thereof in which have affinity for 5-HT1A receptors and which inhibits neuronal reuptake of 5-hydroxytryptamine and/or noradrenaline, to processes for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, obesity, drug addiction, drug abuse, cognitive disorders, Alzheimer’s disease, obsessive-compulsive behaviour, panic attacks, social phobias, eating disorders such as bulimia, anorexia, snacking and binge eating, non-insulin dependent diabetes mellitus, hyperglycaemia, hyperlipidaemia, stress, as an aid to smoking cessation and in the treatment and/or prophylaxis of seizures, neurological disorders such as epilepsy and/or in which there is neurological damage such as stroke, brain trauma, cerebral ischaemia, head injuries and haemorrhage.

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Benzothiophene – Wikipedia,
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N-ALKOXYALKYL-N,N-DIALKYLAMINE DERIVATIVES OR SALTS THEREOF, AND REMEDIES FOR NERVE DEGENERATION DISEASES CONTAINING THE SAME

An N-alkoxyalkyl-N,N-dialkylamine derivative represented by the following general formula [1]:wherein the ring D represents a 5- or 6-membered heterocyclic ring or hydrocarbon ring; R3and R4, which are the same or different, represent an unsubstituted or substituted alkyl, cycloalkyl or aralkyl group; and R1, R2, R5, R6, R7, R8, m and n are as defined in the specification, or a salt thereof has an anti-hypoxic activity, a nerve-protecting activity and a nerve regeneration promoting activity and is useful for the treatment of neurodegenerative diseases.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem