Heterocyclic Building Blocks-Benzothiophene

Tan, Ming published the artcileRoasting treatments affect physicochemical, aroma and nutritional quality of strong fragrant rapeseed oil, Related Products of benzothiophene, the main research area is roasting aroma nutritional quality rapeseed oil.

The strong fragrant rapeseed oil (SFRO) attracts the growing interest in China due to its fragrant flavor, attractive color, and phys. and oxidative stability. It is usually produced with simple processes including rapeseed roasting, mech. pressing, and degumming with hot water (80-90°C). To produce SFROs with high quality and nutritional contents, the seed roasting parameters including temperature up to 220°C and time ranging from 10 min to 30 min were investigated. Results showed that 20-min roasting at temperature 160°C resulted in the highest oil extraction yield of 33.20% with the lowest water content of 0.121%. The produced SFRO had the roasted, nutty and soft tastes with the maximum overall score, the highest total tocopherol and sterol contents of 789.73 mg/kg and 4582.80 mg/kg, resp., and high CoQ10 content of 65.57 mg/kg. Over-roasting at roasting temperature of over 180°C and time of over 30 min led to the high Lovibond red readings, off-flavors, and increased concentrations of high saturated fatty acids and Benzo[a]pyrene (BaP). Our findings would provide a reference to produce SFROs with the highest extraction yield and nutrient contents, acceptable physicochem. properties, optimal profile of the fatty acids and the key aroma compounds, and relatively-low BaP concentration

Journal of Food Composition and Analysis published new progress about Extraction. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Related Products of benzothiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Hicks, Michael B. published the artcileAssessment of coulometric array electrochemical detection coupled with HPLC-UV for the absolute quantitation of pharmaceuticals, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is coulometry electrochem detection liquid chromatog pharmaceutical.

The use of a coulometric array detector in tandem with HPLC-UV was evaluated for the absolute quantitation of pharmaceutical compounds without standards, an important capability gap in contemporary pharmaceutical research and development. The high-efficiency LC flow-through electrochem. detector system allows for the rapid evaluation of up to 16 different potentials, aiding in the identification and quantitation of electrochem. reactive species. By quantifying the number of electrons added or removed from an analyte during its passage through the detector, the number of moles of the analyte can be established. Herein we demonstrate that mols. containing common electroactive functional groups (e.g. anilines, phenols, parabens and tertiary alkyl amines) can in some cases be reliably quantified in HPLC-EC-UV without the need for authentic standards Furthermore, the multichannel nature of the CoulArray detector makes it well suited for optimizing the conditions for electrochem. reaction, allowing the impact of changes in potential, flow rate, temperature and pH to be conveniently studied. The electrochem. oxidation of albacivir, zomepirac, diclofenac, rosiglitazone and several other marketed drugs resulted in large linear ranges, predictable recoveries and excellent quantitation using the total moles of electrons and back-calculating using Faraday’s law. Importantly, we observed several instances where subtle structural changes within a given class of mols. (e.g. aromatic ring isomers) led to unanticipated changes in electrochem. behavior. Consequently, some care should be taken when applying the technique to the routine quantitation of compound libraries where standards are not available.

Analyst (Cambridge, United Kingdom) published new progress about Coulometry. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Cavasin, Anna Theresa published the artcileReliable and Performant Identification of Low-Energy Conformers in the Gas Phase and Water, Safety of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is low energy conformer gas phase water.

Prediction of compound properties from structure via quant. structure-activity relationship and machine-learning approaches is an important computational chem. task in small-mol. drug research. Though many such properties are dependent on three-dimensional structures or even conformer ensembles, the majority of models are based on descriptors derived from two-dimensional structures. Here we present results from a thorough benchmark study of force field, semiempirical, and d. functional methods for the calculation of conformer energies in the gas phase and water solvation as a foundation for the correct identification of relevant low-energy conformers. We find that the tight-binding ansatz GFN-xTB shows the lowest error metrics and highest correlation to the benchmark PBE0-D3(BJ)/def2-TZVP in the gas phase for the computationally fast methods and that in solvent OPLS3 becomes comparable in performance. MMFF94, AM1, and DFTB+ perform worse, whereas the performance-optimized but far more expensive functional PBEh-3c yields energies almost perfectly correlated to the benchmark and should be used whenever affordable. On the basis of our findings, we have implemented a reliable and fast protocol for the identification of low-energy conformers of drug-like mols. in water that can be used for the quantification of strain energy and entropy contributions to target binding as well as for the derivation of conformer-ensemble-dependent mol. descriptors.

Journal of Chemical Information and Modeling published new progress about Conformers. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Safety of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Takakusa, Hideo published the artcileMarkers of electrophilic stress caused by chemically reactive metabolites in human hepatocytes, Quality Control of 40180-04-9, the main research area is drug hepatotoxicity reactive metabolite heme oxygenase biomarker.

The metabolic activation of a drug to an electrophilic reactive metabolite and its covalent binding to cellular macromols. is considered to be involved in the occurrence of idiosyncratic drug toxicity (IDT). As a cellular defense system against oxidative and electrophilic stress, phase II enzymes are known to be induced through a Kelch-like ECH-associated protein 1/nuclear factor E2-related factor 2/antioxidant response element system. We presumed that it is important for the risk assessment of drug-induced hepatotoxicity and IDTs to observe the biol. responses evoked by exposure to reactive metabolites, and then investigated the mRNA induction profiles of phase II enzymes in human hepatocytes after exposure to problematic drugs associated with IDTs, such as ticlopidine, diclofenac, clozapine, and tienilic acid, as well as safe drugs such as levofloxacin and caffeine. According to the results, the problematic drugs exhibited inductive effects on heme oxygenase 1 (HO-1), which contrasted with the safe drugs; therefore, the induction of HO-1 mRNA seems to be correlated with the occurrence of drug toxicity, including IDT caused by electrophilic reactive metabolites. Moreover, glutathione-depletion and cytochrome P 450-inhibition experiments have shown that the observed HO-1 induction was triggered by the electrophilic reactive metabolites produced from the problematic drugs through P 450-mediated metabolic bioactivation. Taken together with our present study, this suggests that HO-1 induction in human hepatocytes would be a good marker of the occurrence of metabolism-based drug-induced hepatotoxicity and IDT caused by the formation of electrophilic reactive metabolites.

Drug Metabolism and Disposition published new progress about Biomarkers. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Quality Control of 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Bala, Snega published the artcileMolecular characterization and identification of copper transport in Wilson disease, Quality Control of 40180-04-9, the main research area is ATP7B diuretic copper mol docking Wilson disease.

Wilson’s disease or hepatolenticular degeneration in an autosomal recessive genetic disorder in which copper accumulates in tissues. The condition is due to mutations in Wilson disease protein (ATP7B). A special feature of WD is that medical therapy is used to treat presymptomatic as well as symptomatic individuals, and hepatic transplantation can reverse the metabolic abnormality. In the present research work, an attempt has been made to map the binding site residues of ATP7B protein (receptor). The 3D structure of the monomeric protein was not yet not been exptl. elucidated for which the theor. structure was determined by homol. modeling using 2UVC as template and the structure was validated and refined by SAVS and MODELLER. The generated 3D structure of ATP7B protein was solvated at 310k and energy minimized using Gromacs. Similarly, 2D structures of several diuretic compounds were retrieved, refined and energy minimized using Arguslab software. The diuretic compounds were then subjected to analyze their adsorption, distribution, metabolism, excretion and their toxicity properties. This anal. was done using the online server PREADME/TOX. The protein-ligand interactions between the ATP7B protein and the diuretic compounds were analyzed using Autodock – PyRx and the docking models were visualized and analyzed by PyMol. Based on the output of the docking models and the binding energies the best lead compound was determined which can be used for fighting against the Wilson disease.

Journal of Computational Methods in Molecular Design published new progress about Asteraceae. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Quality Control of 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Gershbein, Leon L. published the artcileAction of drugs and chemical agents on rat liver regeneration, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is liver regeneration chem drug; hormone liver regeneration; vaccine liver regeneration.

A large number (> 270) of drugs, chems., and other agents were tested for their effects on the regeneration of liver in hepatectomized rats. Seven anticonvulsants, 4 antiinflammatory drugs, 4 sedatives-hypnotics, the antipyretic-analgesic aminopyrine  [58-15-1], the antifungal griseofulvin  [126-07-8], a uricosuric, a muscle relaxant, a hydrocholeretic, an antihypertensive, and a thyroid inhibitor were hepatotrophic. Most the remaining drugs were inactive in this screening, whereas a few suppressed liver regeneration.

Drug and Chemical Toxicology (1977) published new progress about Analgesics. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Sangion, Alessandro published the artcilePBT assessment and prioritization of contaminants of emerging concern: Pharmaceuticals, Application In Synthesis of 40180-04-9, the main research area is persistence bioaccumulation toxicity assessment prioritization contaminant emerging concern pharmaceutical; PBT; Pharmaceuticals; Prioritization; QSAR; Screening.

The strong and widespread use of pharmaceuticals, together with incorrect disposal procedures, has recently made these products contaminants of emerging concern (CEC). Unfortunately, little is known about pharmaceuticals’ environmental behavior and ecotoxicity, so that EMEA (European Medicines Agency) released guidelines for the pharmaceuticals’ environmental risk assessment. In particular, there is a severe lack of information about persistence, bioaccumulation and toxicity (PBT) of the majority of the thousands of substances on the market. Computational tools, like QSAR (Quant. Structure Activity Relationship) models, are the only way to screen large sets of chems. in short time, with the aim of ranking, highlighting and prioritizing the most environmentally hazardous for focusing further exptl. studies. In this work we propose a screening method to assess the potential persistence, bioaccumulation and toxicity of more than 1200 pharmaceutical ingredients, based on the application of two different QSAR models. We applied the Insubria-PBT Index, a MLR (Multiple Linear Regression) QSAR model based on four simple mol. descriptors, implemented in QSARINS software, and able to synthesize the PBT potential in a unique cumulative value and the US-EPA PBT Profiler that assesses the PBT behavior evaluating sep. P, B and T. Particular attention was given to the study of Applicability Domain in order to provide reliable predictions. An agreement of 86% was found between the two models and a priority list of 35 pharmaceuticals, highlighted as potential PBTs by consensus, was proposed for further exptl. validation. Moreover, the results of this computational screening are in agreement with preliminary exptl. data in the literature. This study shows how in silico models can be applied in the hazard assessment to perform preliminary screening and prioritization of chems., and how the identification of the structural features, mainly associated with the potential PBT behavior of the prioritized pharmaceuticals, is particularly relevant to perform the rational a priori design of new, environmentally safer, pharmaceuticals.

Environmental Research published new progress about Analgesics. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Application In Synthesis of 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Chan, Alix I. published the artcileDiscovery of a Covalent Kinase Inhibitor from a DNA-Encoded Small-Molecule Library × Protein Library Selection, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is human kinase MAP2K6 inhibitor DNA encoded small mol library.

We previously reported interaction determination using unpurified proteins (IDUP), a method to selectively amplify DNA sequences encoding ligand:target pairs from a mixture of DNA-linked small mols. and unpurified protein targets in cell lysates. In this study we applied IDUP to libraries of DNA-encoded bioactive compounds and DNA-tagged human kinases to identify ligand:protein binding partners out of 32,096 possible combinations in a single solution-phase library × library experiment The results recapitulated known small mol.:protein interactions and also revealed that ethacrynic acid is a novel ligand and inhibitor of MAP2K6 kinase. Ethacrynic acid inhibits MAP2K6 in part through alkylation of a non-conserved cysteine residue. This work validates the ability of IDUP to discover ligands for proteins of biomedical relevance.

Journal of the American Chemical Society published new progress about Alkylation. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Lopez-Garcia, M. Pilar published the artcileThiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: Inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid, Name: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is thiophene derivative cytochrome P4502C9 suicide substrate; tienilate metabolite cytochrome P4502C9 suicide substrate; immunoallergic hepatitis tienilate metabolite cytochrome P4502C9.

Oxidation of tienilic acid (TA) by microsomes of yeast expressing two closely related human liver cytochrome P-450s (P 450), P 450 2C9 and 2C10, led to catalysis-dependent loss of activity of these P450s. Under identical conditions, oxidation of a tienilic acid isomer (TAI) failed to give any P 450 inactivation. The loss of P 450 activity during TA oxidation was concomitant with product (5-hydroxytienilic acid, 5-OHTA) formulation, showed pseudo-first-order and saturation kinetics, and was inhibited by an alternative substrate, tolbutamide. Covalent binding of TA metabolites to microsomal proteins occurred in parallel with enzyme inactivation and was partially inhibited by the presence of glutathione in the reaction medium. However, glutathione did not protect P 450 enzyme from inactivation. Thus, TA exhibited all of the characteristics of a mechanism-based inactivator for P 450 2C9 and 2C10 enzymes. The following kinetic parameters were determined in the case of P 450 2C10: t1/2,max = 3.4 min, kinact = 3.6 10-3 s-1, KI = 4.3 μM, kinact/K1 = 813 L mol-1 s-1, and partition ratio = 11.6. Moreover, a specific covalent binding of 0.9 mol of TA metabolite per mol of P 450 2C10 was found to occur before the complete loss of enzyme activity (in incubations performed in the presence of glutathione). A plausible mechanism for P 450 2C10 (2C9) inactivation during TA oxidation is proposed. It involves the intermediate formation of an electrophilic thiophene sulfoxide, which may react at position 5 of its thiophene ring either with H2O to give 5-OHTA or with a nucleophilic group of an amino acid residue of the P 450 active site, which results in its covalent binding to P 450 protein. This alkylation and inactivation of P 450 2C9 (2C10) by TA could be a starting point for the appearance of anti-P 4502C antibodies detected in patients treated with TA and suffering from immunoallergic hepatitis.

Biochemistry published new progress about Alkylation. 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Name: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Wang, Guang-Zu published the artcilePhotocatalytic decarboxylative alkylations of C(sp3)-H and C(sp2)-H bonds enabled by ammonium iodide in amide solvent, Quality Control of 1468-83-3, the main research area is alkylate glycine heteroarene regioselective; aryl glycine heteroarene hydroxyphthalimide redox ester; ammonium iodide salt catalyst decarboxylative alkylation.

A simple ammonium iodide salt in amide solvent catalyzes regioselective decarboxylative alkylation of C(sp3)-H bonds of N-aryl glycine derivatives, of C(sp2)-H bond of heteroarenes, and cascade radical addition to unsaturated bond followed by intramol. addition to arene, with a broad scope of N-hydroxyphthalimide derived redox active esters under visible light irradiation The reactions are suggested to proceed through photoactivation of a transiently assembled chromophore from electron-deficient phthalimide moiety and iodide anion through an anion-π interaction in solvent cage followed by diffusion to generate solvated free radical species to react with C-H substrates. The simplicity, practicality, and broad substrate scope of this method highlight the synthetic power of photocatalysis through transiently assembled chromophore, and will hopefully inspire further developments of low cost photocatalysis based on various non-covalent interactions, which are prevalent in supramol. chem. and biosystems, for sustainable organic synthesis.

Science China: Chemistry published new progress about Alkylation. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Quality Control of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem