Month: November 2022

Fujimoto, Hayato published the artcileThree-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis, Related Products of benzothiophene, the main research area is diene preparation hydrovinylation phosphine catalyst; acyl fluoride silyl enol ether alkynoate three component coupling.

Authors report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.

Journal of the American Chemical Society published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent) (alkynoates). 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

Zhao, Yue published the artcilePhotochemical (Hetero-)Arylation of Aryl Sulfonium Salts, Name: 3-Acetylthiophene, the main research area is aryl thianthrenium salt heteroarene light photochem arylation; heterobiaryl preparation.

The construction of (hetero)biaryls, which are ubiquitous scaffolds among medical substances, functional materials, and agrochems., constitutes a key application of cross-coupling methods. However, these usually require multiple synthetic steps. Herein, we report a simple photoinduced and catalyst-free C-H/C-H (hetero)arylation cross-coupling through aryl thianthrenium salts, which are formed site-selectively by direct C-H functionalization. The key to this approach is the UV-light, which can disrupt the C-S bond to form thianthrene radical cations and aryl radicals.

Organic Letters published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Name: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Aukland, Miles H. published the artcileMetal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation, Computed Properties of 1468-83-3, the main research area is arene heteroarene dibenzothiophene oxide photocatalyst regioselective cross coupling reaction; heterobiaryl preparation.

An expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners was reported. The approach was underpinned by the functionalization of a C-H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy was exemplified by the synthesis of a bioactive natural product and the modification of complex mols. of societal importance.

Nature Catalysis published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Computed Properties of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Antenucci, Achille published the artcileIron(III)-Catalyzed Hydration of Unactivated Internal Alkynes in Weak Acidic Medium, under Lewis Acid-Assisted Bronsted Acid Catalysis, HPLC of Formula: 1468-83-3, the main research area is arylketone preparation regioselective; internal alkyne hydration iron Lewis Bronsted acid catalyst.

Alkylarylalkynes, e.g., I are converted with full regioselectivity into the corresponding arylketones, e.g., II by formal hydration of the triple bond under weak acidic conditions, at times and temperatures (â‰?5 °C) comparable to those used for terminal alkynes. The process catalyzed by Fe2(SO4)3nH2O in glacial acetic acid exhibits good functional group compatibility, including that with bulky triple bond substituents, and can be extended to the one-pot transformation of aryltrimethylsilylacetylenes ArCCSi(CH3)3 (Ar = thiophen-3-yl, 3,5-(OCH3)2C6H3, 3-F3CC6H4) into acetyl derivatives ArC(O)CH3 via a desilylation-hydration sequence. The overall reactivity pattern along with proton affinity data indicate that the triple bond is activated by proton transfer rather than by π-interaction with the metal ion. This mechanistic feature, at variance with that of noble metal catalysts, accounts for the total regioselectivity and the insensitivity to steric hindrance exhibited by the Fe2(SO4)3nH2O/AcOH catalytic system.

Advanced Synthesis & Catalysis published new progress about Alkyl aryl ketones Role: SPN (Synthetic Preparation), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, HPLC of Formula: 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Xu, Jingxiu published the artcileN-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature, Quality Control of 1468-83-3, the main research area is quinoline preparation; aminobenzyl alc Friedlander reaction ketone heterocyclic carbene catalyst.

A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedlander reaction from 2-aminobenzyl alc. and aryl ketones using DMSO as an oxidant at room temperature is reported. The quinolines, e.g., I (R1 = 4-MeC6H4, 2-ClC6H4, 3-thienyl, etc., R2 = H; R1 = Ph, R2 = Me), were synthesized in acceptable yields.

RSC Advances published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent) (amino). 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

Rao, Ponugoti published the artcileEffects of novel ethacrynic acid derivatives on human trabecular meshwork cell shape, actin cytoskeletal organization, and transcellular fluid flow, COA of Formula: C13H8Cl2O4S, the main research area is ethacrynic acid derivative trabecular meshwork actin cytoskeleton transcellular fluid.

To determine efficacy and therapeutic index in the context of ocular hypotensive activity of the new ethacrynic acid (ECA) derivatives of the 8000 series (SA8248 and SA8389), 9000 series (SA9000, SA9622 and SA9995) and ticrynafen, we undertook a comparative evaluation of the dose-dependent effects of these compounds on human trabecular meshwork (HTM) cell shape, actin cytoskeletal organization, focal adhesions and transcellular fluid flow. Responses were either scored using an arbitrary scale of 1 – 5 or quantified. Compounds of the 9000 series (SA9995 >SA9000 >SA9622) were found to be 14- to 20-fold more potent than ECA, ticrynafen or analogs from the 8000 series (SA8389>SA8248) in terms of ability to induce cell shape alterations in HTM cells. Similarly, compounds of the 9000 series (SA9995 >SA9622 >SA9000) were found to be much stronger (2 to 20 fold) than ECA, ticrynafen or analogs of the 8000 series in terms of affecting decreases in actin stress fiber content in HTM cells. Analogs of the 9000 series (SA9622 >SA9995 >SA9000) were also observed to be 8 to 10 fold more potent than ECA (SA8389 >ECA >SA8248 >ticrynafen) at eliciting decreases in cellular focal adhesions. Interestingly, analogs of the 9000 series (SA9000>SA9622>SA9995) and SA8248 demonstrated a huge increase (by many folds) in transcellular fluid flow of HTM cell monolayers as compared to ECA and ticrynafen. Collectively, these analyses revealed that the structural modification of ECA improves its ocular hypotensive efficacy, indicating that the SA9000 series compounds might be promising novel ocular hypotensive drugs.

Biological & Pharmaceutical Bulletin published new progress about Actins Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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, COA of Formula: C13H8Cl2O4S.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Pumford, Neil R. published the artcileProtein targets of xenobiotic reactive intermediates, Application of 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is protein target xenobiotic reactive intermediate review.

A review and discussion with 168 references Many xenobiotics are metabolically activated to electrophilic intermediates that form covalent adducts with proteins; the mechanism of toxicity is either intrinsic or idiosyncratic in nature. Many intrinsic toxins covalently modify cellular proteins and somehow initiate a sequence of events that leads to toxicity. Major protein adducts of several intrinsic toxins have been identified and demonstrate significant decrease in enzymic activity. The reactivity of intermediates and subcellular localization of major targets maybe important in the toxicity. Major protein adducts of several intrinsic toxins have been identified and demonstrate significant decreases in enzymic activity. The reactivity of intermediates and subcellular localization of major targets may be important in the toxicity. Idiosyncratic toxicities are mediated through either a metabolic or immune-mediated mechanism. Xenobiotics that cause hypersensitivity/autoimmunity appear to have a limited number of protein targets, which are localized within the subcellular fraction where the electrophile is produced, are highly substituted, and are accessible to the immune system. Metabolic idiosyncratic toxins appear to have limited targets and are localized within a specific subcellular fraction. Identification of protein targets has given us insights into mechanisms of xenobiotic toxicity.

Annual Review of Pharmacology and Toxicology published new progress about Proteins Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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

Hosaka, Shuto published the artcileBiomimetic trapping cocktail to screen reactive metabolites: use of an amino acid and DNA motif mixture as light/heavy isotope pairs differing in mass shift, Quality Control of 40180-04-9, the main research area is biomimetic trapping cocktail metabolite mass spectrometry drug screening; Activated drug; Cocktail reagent; Mass spectrometry; Trapping reagent.

Candidate drugs that can be metabolically transformed into reactive electrophilic products, such as epoxides, quinones, and nitroso compounds, are of special concern because subsequent covalent binding to bio-macromols. can cause adverse drug reactions, such as allergic reactions, hepatotoxicity, and genotoxicity. Several strategies have been reported for screening reactive metabolites, such as a covalent binding assay with radioisotope-labeled drugs and a trapping method followed by LC-MS/MS analyses. Of these, a trapping method using glutathione is the most common, especially at the early stage of drug development. However, the cysteine of glutathione is not the only nucleophilic site in vivo; lysine, histidine, arginine, and DNA bases are also nucleophilic. Indeed, the glutathione trapping method tends to overlook several types of reactive metabolites, such as aldehydes, acylglucuronides, and nitroso compounds Here, we introduce an alternate way for screening reactive metabolites as follows: A mixture of the light and heavy isotopes of simplified amino acid motifs and a DNA motif is used as a biomimetic trapping cocktail. This mixture consists of [2H0]/[2H3]-1-methylguanidine (arginine motif, Δ 3 Da), [2H0]/[2H4]-2-mercaptoethanol (cysteine motif, Δ 4 Da), [2H0]/[2H5]-4-methylimidazole (histidine motif, Δ 5 Da), [2H0]/[2H9]-n-butylamine (lysine motif, Δ 9 Da), and [13C0,15N0]/[13C1,15N2]-2′-deoxyguanosine (DNA motif, Δ 3 Da). Mass tag triggered data-dependent acquisition is used to find the characteristic doublet peaks, followed by specific identification of the light isotope peak using MS/MS. Forty-two model drugs were examined using an in vitro microsome experiment to validate the strategy. [Figure not available: see fulltext.].

Analytical and Bioanalytical Chemistry published new progress about DNA Role: ARG (Analytical Reagent Use), ANST (Analytical Study), USES (Uses). 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

Sharma, Ashok K. published the artcileToxiM: a toxicity prediction tool for small molecules developed using machine learning and chemoinformatics approaches, Formula: C13H8Cl2O4S, the main research area is hepatotoxicity ToxiM machine learning chemoinformatics asbestos ethylene glycol; chemoinformatics; classification models; machine leaning; permeability; regression model; solubility; toxicity prediction.

The exptl. methods for the prediction of mol. toxicity are tedious and time-consuming tasks. Thus, the computational approaches could be used to develop alternative methods for toxicity prediction. We have developed a tool for the prediction of mol. toxicity along with the aqueous solubility and permeability of any mol./metabolite. Using a comprehensive and curated set of toxin mols. as a training set, the different chem. and structural based features such as descriptors and fingerprints were exploited for feature selection, optimization and development of machine learning based classification and regression models. The compositional differences in the distribution of atoms were apparent between toxins and non-toxins, and hence, the mol. features were used for the classification and regression. On 10-fold cross-validation, the descriptor-based, fingerprint-based and hybrid-based classification models showed similar accuracy (93%) and Matthews’s correlation coefficient (0.84). The performances of all the three models were comparable (Matthews’s correlation coefficient = 0.84-0.87) on the blind dataset. In addition, the regression-based models using descriptors as input features were also compared and evaluated on the blind dataset. Random forest based regression model for the prediction of solubility performed better (R2 = 0.84) than the multi-linear regression (MLR) and partial least square regression (PLSR) models, whereas, the partial least squares based regression model for the prediction of permeability (caco-2) performed better (R2 = 0.68) in comparison to the random forest and MLR based regression models. The performance of final classification and regression models was evaluated using the two validation datasets including the known toxins and commonly used constituents of health products, which attests to its accuracy. The ToxiM web server would be a highly useful and reliable tool for the prediction of toxicity, solubility, and permeability of small mols.

Frontiers in Pharmacology published new progress about Asbestos Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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, Formula: C13H8Cl2O4S.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Satoh, Daisuke published the artcileEstablishment of a novel hepatocyte model that expresses four cytochrome P450 genes stably via mammalian-derived artificial chromosome for pharmacokinetics and toxicity studies, SDS of cas: 40180-04-9, the main research area is hepatocyte cytochrome P450 artificial chromosome pharmacokinetics toxicity.

The utility of HepG2 cells to assess drug metabolism and toxicity induced by chem. compounds is hampered by their low cytochrome P 450 (CYP) activities. To overcome this limitation, we established HepG2 cell lines expressing major CYP enzymes involved in drug metabolism (CYP2C9, CYP2C19, CYP2D6, and CYP3A4) and CYP oxidoreductase (POR) using the mammalian-derived artificial chromosome vector. Transchromosomic HepG2 (TC-HepG2) cells expressing four CYPs and POR were used to determine time- and concentration-dependent inhibition and toxicity of several compounds by luminescence detection of CYP-specific substrates and cell viability assays. Gene expression levels of all four CYPs and POR, as well as the CYP activities, were higher in TC-HepG2 clones than in parental HepG2 cells. Addnl., the activity levels of all CYPs were reduced in a concentration-dependent manner by specific CYP inhibitors. Furthermore, preincubation of TC-HepG2 cells with CYP inhibitors known as time-dependent inhibitors (TDI) prior to the addition of CYP-specific substrates determined that CYP inhibition was enhanced in the TDI group than in the non-TDI group. Finally, the IC50 of bioactivable compound aflatoxin B1 was lower in TC-HepG2 cells than in HepG2 cells. In conclusion, the TC-HepG2 cells characterized in the current study are a highly versatile model to evaluate drug-drug interactions and hepatotoxicity in initial screening of candidate drug compounds, which require a high degree of processing capacity and reliability.

PLoS One published new progress about Albumins Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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, SDS of cas: 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem