Month: November 2022

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

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

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

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

Dong, Xiao-Yang published the artcileCopper-Catalyzed Asymmetric Coupling of Allenyl Radicals with Terminal Alkynes to Access Tetrasubstituted Allenes, Synthetic Route of 1468-83-3, the main research area is enyne alkyne alkyl bromide copper carboalkynylation catalyst; allene stereoselective preparation; 1,4-enynes; alkyl bromides; allenes; asymmetric radical reactions; copper.

In contrast to the wealth of asym. transformations for generating central chirality from alkyl radicals, the enantiocontrol over the allenyl radicals for forging axial chirality represents an uncharted domain. The challenge arises from the unique elongated linear configuration of the allenyl radicals that necessitates the stereo-differentiation of remote motifs away from the radical reaction site. We herein describe a copper-catalyzed asym. radical 1,4-carboalkynylation of 1,3-enynes via the coupling of allenyl radicals with terminal alkynes, providing diverse synthetically challenging tetrasubstituted chiral allenes. A chiral N,N,P-ligand is crucial for both the reaction initiation and the enantiocontrol over the highly reactive allenyl radicals. The reaction features a broad substrate scope, covering a variety of (hetero)aryl and alkyl alkynes and 1,3-enynes as well as radical precursors with excellent functional group tolerance.

Angewandte Chemie, International Edition published new progress about Alkynes, α- Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Synthetic Route of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Zhang, Guan published the artcileN2H4-H2O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides, Application In Synthesis of 1468-83-3, the main research area is quinoline oxide green preparation; nitrochalcone hydrazine hydrate umpolung cyclization.

Umpolung was a unique strategy which converts the property of an atom into the opposite one. An efficient and general method for the construction of quinoline N-oxides I [R = Me, Ph, 2-pyridyl, etc.; R1 = 6-F, 6-Br, 6,7-di-OMe, etc.] via umpolung of carbonyl groups was developed from ortho-nitro chalcones and hydrazine in basic conditions. The strategy was transition-metal free and had good functional group tolerance, environmental friendliness, as well as mild reaction conditions with nitrogen gas as the byproduct.

Organic Letters published new progress about Cyclization. 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

Cao, Haoying published the artcileSynthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis, Category: benzothiophene, the main research area is beta nitro ketone preparation; geminal bromonitroalkane silyl enol ether visible light photoredox catalysis.

Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis. Products which were then easily converted into β-amino ketones, 1,3-amino alcs., α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.

Chemical Communications (Cambridge, United Kingdom) published new progress about Coupling reaction catalysts. 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

Beaune, P. H. published the artcileAnti-cytochrome P450 autoantibodies in drug-induced disease, Related Products of benzothiophene, the main research area is review cytochrome P450 autoantibody drug.

A review with 23 references Drugs may induce hepatitis through immune mechanisms. In this review we have used the examples of 2 drugs to elucidate the first steps leading to the triggering of such disease, namely tienilic acid (TA) and dihydralazine (DH). These drugs are transformed into reactive metabolite(s) by cytochrome P 450 (2C9 for TA and 1A2 for DH) (step 1). The reactive metabolites produced are very short-lived and bind directly to the enzymes which generated them (step 2). A neoantigen is thus formed which triggers an immune response (step 3), characterized by the presence of autoantibodies in the patient’s serum (step 4). The autoantibodies are directed against the cytochrome P 450 which generated the metabolite(s). Although the process by which TA and DH induce hepatitis has been elucidated, further studies are necessary to generalize this mechanism. In addition, an animal model will also be useful to fully understand the immune mechanism of this type of disease.

European Journal of Haematology, Supplementum published new progress about Drugs. 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, Related Products of benzothiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Thompson, Richard A. published the artcileIn Vitro Approach to Assess the Potential for Risk of Idiosyncratic Adverse Reactions Caused by Candidate Drugs, Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is risk idiosyncratic adverse drug.

Idiosyncratic adverse drug reactions (IADRs) in humans can result in a broad range of clin. significant toxicities leading to attrition during drug development as well as postlicensing withdrawal or labeling. IADRs arise from both drug and patient related mechanisms and risk factors. Drug related risk factors, resulting from parent compound or metabolites, may involve multiple contributory mechanisms including organelle toxicity, effects related to compound disposition, and/or immune activation. In the current study, we evaluate an in vitro approach, which explored both cellular effects and covalent binding (CVB) to assess IADR risks for drug candidates using 36 drugs which caused different patterns and severities of IADRs in humans. The cellular effects were tested in an in vitro Panel of five assays which quantified (1) toxicity to THLE cells (SV40 T-antigen-immortalized human liver epithelial cells), which do not express P450s, (2) toxicity to a THLE cell line which selectively expresses P 450 3A4, (3) cytotoxicity in HepG2 cells in glucose and galactose media, which is indicative of mitochondrial injury, (4) inhibition of the human bile salt export pump, BSEP, and (5) inhibition of the rat multidrug resistance associated protein 2, Mrp2. In addition, the CVB Burden was estimated by determining the CVB of radiolabeled compound to human hepatocytes and factoring in both the maximum prescribed daily dose and the fraction of metabolism leading to CVB. Combining the aggregated results from the in vitro Panel assays with the CVB Burden data discriminated, with high specificity (78%) and sensitivity (100%), between 27 drugs, which had severe or marked IADR concern, and 9 drugs, which had low IADR concern, we propose that this integrated approach has the potential to enable selection of drug candidates with reduced propensity to cause IADRs in humans.

Chemical Research in Toxicology published new progress about Cytotoxicity. 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, Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Williams, Dominic P. published the artcilePredicting Drug-Induced Liver Injury with Bayesian Machine Learning, Related Products of benzothiophene, the main research area is machine learning drug liver toxicity prediction risk assessment.

Drug induced liver injury (DILI) can require significant risk management in drug development, and on occasion can cause morbidity or mortality, leading to drug attrition. Optimizing candidates preclinically can minimise hepatotoxicity risk but it is difficult to predict due to multiple etiologies encompassing DILI, often with multifactorial and overlapping mechanisms. In addition to epidemiol. risk factors, physicochem. properties, dose, disposition, lipophilicity, and hepatic metabolic function are also relevant for DILI risk. Better human relevant, predictive models are required to improve hepatotoxicity risk assessment in drug discovery. The authors’ hypothesis is that integrating mechanistically relevant hepatic safety assays with Bayesian machine learning will improve hepatic safety risk prediction. The authors present a quant. and mechanistic risk assessment for candidate nomination using data from in vitro assays (hepatic spheroids, BSEP, mitochondrial toxicity and bioactivation), together with physicochem. (cLogP) and exposure (Cmaxtotal) variables from a chem. diverse compound set (33 no/low-, 40 medium- and 23 high-severity DILI compounds). The Bayesian model predicts the continuous underlying DILI severity and uses a data-driven prior distribution over the parameters to prevent overfitting. The model quantifies the probability that a compound falls into either no/low, medium, or high-severity categories, with a balanced accuracy of 63% on held-out samples, and a continuous prediction of DILI severity along with uncertainty in the prediction. For a binary yes/no DILI prediction, the model has a balanced accuracy of 86%, a sensitivity of 87%, a specificity of 85%, a pos. predictive value of 92%, and a neg. predictive value of 78%. Combining physiol. relevant assays, improved alignment with FDA recommendations, and optimal statistical integration of assay data, leads to improved DILI risk prediction.

Chemical Research in Toxicology published new progress about Biotransformation. 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, Related Products of benzothiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem