Category: benzothiophene

Petersen, Karina published the artcileToxicity of organic compounds from unresolved complex mixtures (UCMs) to primary fish hepatocytes, HPLC of Formula: 19156-54-8, the main research area is Oncorhynchus hepatocyte toxicity unresolved complex mixture; AhR agonist; Cytotoxicity; ER agonist; EROD; Naphthenic acids; Vitellogenin; Xenoestrogen; in vitro.

In the present study, several chems. with structures typical of those found in some UCMs, were assessed for their potential to disrupt membrane integrity, inhibit metabolic activity, activate the aryl hydrocarbon receptor (AhR), and activate the estrogen receptor (ER) in primary rainbow trout hepatocytes (Oncorhynchus mykiss). These endpoints were determined in order to screen for common toxic modes of action (MoA) in this diverse group of chems. EC50 values for cytotoxicity were obtained for 16 compounds and ranged from 77μM-24 mM, whereof aliphatic monocyclic acids, monoarom. acids, polycyclic monoarom. acids and alkylnaphthalenes were the most toxic. The observed cytotoxicity of the chems. correlated well with the hydrophobicity (LogKOW) suggesting that the toxicity was predominantly due to a non-specific MoA. Interestingly, two compounds induced the ER-mediated production of vitellogenin (Vtg) and six compounds induced the AhR-mediated Ethoxyresorufin-O-deethylase (EROD) enzymic activity to >20% of the pos. control; by doing so suggesting that they may act as ER or AhR agonists in fish. The heterogeneous group of ‘UCM compounds’ tested exhibited multiple MoA that may potentially cause adverse effects in fish. Addnl. studies to determine if these compounds may cause adverse effects in vivo at environmentally relevant concentrations, are warranted to identify if such compounds are indeed of potential environmental concern.

Aquatic Toxicology published new progress about Canned fish, rainbow trout. 19156-54-8 belongs to class benzothiophene, name is 4,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxylic acid, and the molecular formula is C9H10O2S, HPLC of Formula: 19156-54-8.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Yu, Rongrong published the artcileHighly Enantioselective Nickel-Catalyzed Hydrocyanation of Disubstituted Methylenecyclopropanes Enabled by TADDOL-based Diphosphite Ligands, Application In Synthesis of 1468-83-3, the main research area is nickel catalyzed enantioselective hydrocyanation methylenecyclopropane TADDOL phosphite.

A vast range of novel TADDOL-based diphosphite ligands were first synthesized and applied in the nickel-catalyzed asym. hydrocyanation of disubstituted methylenecyclopropanes. By employing these new catalysts, the conversion of diverse methylenecyclopropanes into their corresponding allylic nitriles was first enabled, in good yield with excellent enantioselectivities.

Organic Letters published new progress about Cyclopropanes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (methylenecyclopropanes). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Application In Synthesis of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Liu, Ruifeng published the artcile2D SMARTCyp Reactivity-Based Site of Metabolism Prediction for Major Drug-Metabolizing Cytochrome P450 Enzymes, Formula: C13H8Cl2O4S, the main research area is SMARTCyp cytochrome P450 3A4 2D6 2C9 2C19 1A2 human.

Cytochrome P 450 (CYP) 3A4, 2D6, 2C9, 2C19, and 1A2 are the most important drug-metabolizing enzymes in the human liver. Knowledge of which parts of a drug mol. are subject to metabolic reactions catalyzed by these enzymes is crucial for rational drug design to mitigate ADME/toxicity issues. SMARTCyp, a recently developed 2D ligand structure-based method, is able to predict site-specific metabolic reactivity of CYP3A4 and CYP2D6 substrates with an accuracy that rivals the best and more computationally demanding 3D structure-based methods. In this article, the SMARTCyp approach was extended to predict the metabolic hotspots for CYP2C9, CYP2C19, and CYP1A2 substrates. This was accomplished by taking into account the impact of a key substrate-receptor recognition feature of each enzyme as a correction term to the SMARTCyp reactivity. The corrected reactivity was then used to rank order the likely sites of CYP-mediated metabolic reactions. For 60 CYP1A2 substrates, the observed major sites of CYP1A2 catalyzed metabolic reactions were among the top-ranked 1, 2, and 3 positions in 67%, 80%, and 83% of the cases, resp. The results were similar to those obtained by MetaSite and the reactivity + docking approach. For 70 CYP2C9 substrates, the observed sites of CYP2C9 metabolism were among the top-ranked 1, 2, and 3 positions in 66%, 86%, and 87% of the cases, resp. These results were better than the corresponding results of StarDrop version 5.0, which were 61%, 73%, and 77%, resp. For 36 compounds metabolized by CYP2C19, the observed sites of metabolism were found to be among the top-ranked 1, 2, and 3 sites in 78%, 89%, and 94% of the cases, resp. The computational procedure was implemented as an extension to the program SMARTCyp 2.0. With the extension, the program can now predict the site of metabolism for all five major drug-metabolizing enzymes with an accuracy similar to or better than that achieved by the best 3D structure-based methods. Both the Java source code and the binary executable of the program are freely available to interested users.

Journal of Chemical Information and Modeling published new progress about Algorithm (SMARTCyp, 2D ligand structure-based method). 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

Chesman, Anthony S. R. published the artcileSome Products from C=O Condensations of Quinacridones, Recommanded Product: 3-Acetylthiophene, the main research area is quinacridone condensation nucleophile phosphoryl chloride.

Quinacridone chem. has been developed which provides a source of new compounds that have potential application in organic photovoltaic (OPV) devices. Phosphoryl chloride is used for the conversion of carbonyl groups in N,N’-dialkylquinacridones, generating reactive intermediates that enable selective condensation with either one or two nucleophilic mols. under mild conditions. Thus, e.g., treatment of 5,12-dioctylquinacridone with Me cyanoacetate in presence of POCl3 afforded I (74%).

Australian Journal of Chemistry published new progress about Acridones Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Wang, Ying-Ying published the artcileRh(III)-Catalyzed multi-site-selective C-H bond functionalization: condition-controlled synthesis of diverse fused polycyclic benzimidazole derivatives, Quality Control of 1468-83-3, the main research area is phenoxybenzimidazole hydroxybutynoate rhodium catalyst tandem activation cyclization Michael addition; spirobenzobenzoimidazooxazine furanone preparation; dihydrofuranyl spirobenzobenzoimidazooxazine furanone preparation; spirobenzoimidazo difuronaphthooxazine furan trione preparation.

Novel fused polycyclic- and multi-substituted 2-oxyl naphthalene benzimidazole derivatives were selectively synthesized via Rh(III)-catalyzed tandem C-H activation/cyclization. The efficient strategy for the construction of diverse annulation products was precisely controlled by changing the reaction conditions.

Organic Chemistry Frontiers published new progress about Alkenylation. 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

Zheng, Wei-Feng published the artcileTetrasubstituted allenes via the palladium-catalysed kinetic resolution of propargylic alcohols using a supporting ligand, Application of 3-Acetylthiophene, the main research area is allenoic acid preparation enantioselective; propargylic alc kinetic resolution carboxylation reaction palladium catalyst.

A straightforward catalytic asym. synthesis of tetrasubstituted 2,3-allenoic acids I (R1 = Bu, iso-Pr, 2-phenylethyl, etc.; R2 = Ph, thiophen-3-yl, cyclohexyl, etc.; R3 = Me, Et; R2R3 = 1,2,3,4-tetrahydronaphthalen-1-ylidene) from readily available racemic propargylic alcs. R1CCC(R2)(R3)(OH) has been reported. Enabled by the co-catalysis of palladium and a Bronsted acid in the presence of a com. available chiral ligand (DTBM-SEGphos) and an achiral monophosphine supporting ligand (PPh3), the kinetic resolution of propargylic alcs. proceeded efficiently in the presence of water and 1 atm CO, affording tetrasubstituted 2,3-allenoic acids in excellent enantioselectivity and atom economy with a good functional group compatibility. Performing a second kinetic resolution on the unreacted alc. gave access to the other enantiomer of the product. These allenes are precursors to compounds with quaternary carbon centers and other chiral tetrasubstituted allene building blocks, which are of great interest.

Nature Catalysis published new progress about Allenes Role: SPN (Synthetic Preparation), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Application of 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Gonzalez-Granda, Sergio published the artcileAlcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols, Category: benzothiophene, the main research area is propargylic alc Meyer Schuster rearrangement gold catalyst enzymic reduction; allylic alc enantioselective synthesis; alcohols; enzymes; gold; rearrangements; stereoselectivity.

The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer-Schuster rearrangement of a series of readily available propargylic alcs. followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcs. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alc. dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65-86%). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives The use of alc. dehydrogenases of opposite selectivity led to the production of both allyl alc. enantiomers (93->99% ee) for a broad panel of substrates.

Angewandte Chemie, International Edition published new progress about Allylic alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Category: benzothiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Schmalzbauer, Matthias published the artcileRedox-Neutral Photocatalytic C-H Carboxylation of Arenes and Styrenes with CO2, Recommanded Product: 3-Acetylthiophene, the main research area is aryl carboxylic acid preparation; arene carbon dioxide redox neutral photocatalytic CH carboxylation; cinnamic acid diastereoselective preparation; styrene carbon dioxide redox neutral photocatalytic CH carboxylation.

A redox-neutral CH carboxylation of arenes and styrenes using a photocatalytic approach was described for the synthesis of aryl/unsaturated-carboxylic acids RCOOH [R = 1-naphthyl, CH=CHPh, 5-cyano-2-thienyl, etc.]. Upon blue-light excitation, the anthrolate anion photocatalyst was able to reduce many aromatic compounds to their corresponding radical anions, which react with CO2 to afford carboxylic acids. High-throughput screening and computational anal. suggest that a correct balance between electron affinity and nucleophilicity of substrates was essential. This novel methodol. enabled the carboxylation of numerous aromatic compounds, including many that were not tolerated in classical carboxylation chem. Over 50 examples of CH functionalizations using CO2 or ketones illustrated a broad applicability.

Chem published new progress about Carboxylation. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Dai, Zengjin published the artcileDirect reductive amination of ketones with ammonium salt catalysed by Cp*Ir(III) complexes bearing an amidato ligand, COA of Formula: C6H6OS, the main research area is half sandwich iridium complex amidato bidentate ligand preparation; racemic alpha chiral primary amine preparation; ketone direct reductive amination Leuckart Wallach reaction.

A series of half-sandwich Ir(III) complexes bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex I, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Asym. transformation was also attempted with chiral Ir complexes, and 16% ee of the desired primary amine was obtained. Despite the unsatisfactory enantio-control achieved so far, the current exploration might stimulate more efforts towards the discovery of better chiral catalysts for this challenging but important transformation.

Organic & Biomolecular Chemistry published new progress about Ketones Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, COA of Formula: C6H6OS.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Wang, Wei published the artcileDiastereo- and Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters via Iridium/Europium Bimetallic Catalysis, Application of 3-Acetylthiophene, the main research area is allyl carbonate oxindole iridium catalyst diastereoselective enantioselective allylation; Allylic Alkylation; Allylic Electrophiles; Bimetallic Catalysis; N,N′-Dioxide; Quaternary Stereocenters.

The diastereo- and enantioselective construction of vicinal all-carbon quaternary stereocenters is a formidable task. We here report a synergistic bimetallic catalysis via a chiral N,N′-dioxide-europium (Eu) complex and a phosphoramidite-iridium (Ir) catalyst for the asym. allylation of oxindole derivatives by using challenging trisubstituted allylic esters. The allylated products bearing vicinal all-carbon quaternary stereocenters were obtained with good diastereoselectivities (up to 20 : 1 dr) and excellent enantioselectivities (up to 99 % ee). Control experiments showed that the complementary diastereomers of the products were not accessible by the change of the stereochem. of the chiral N,N′-dioxide ligand.

Angewandte Chemie, International Edition published new progress about Allylation catalysts, stereoselective. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Application of 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem