Heterocyclic Building Blocks-Benzothiophene

Snow, Ina B. published the artcileRenal sites of natriuretic and uricosuric activity of ticrynafen in the mongrel dog, Quality Control of 40180-04-9, the main research area is ticrynafen natriuresis uricosuria mechanism; resorption uric acid sodium ticrynafen.

Following establishment of steady state plasma concentrations of ticrynafen (I) [40180-04-9] in the mongrel dog, the i.v. injection of large doses of p-aminohippurate (PAH) or Na salicylate reduced or blocked the urinary excretion of I. In a similar manner, the i.v. administration of I reduced the urinary excretion of PAH in preloaded dogs. Since PAH and salicylate are actively secreted by a renal tubular organic anion transport system, these data provided evidence for an active tubular secretion of I. The natriuresis and uricosuria from the administration of I to the mongrel dog were reduced by PAH and salicylate at doses which effectively blocked the secretion of I. Apparently, in the dog, the natriuretic and uricosuric activity of I results from the presence of I in the tubular lumen.

Nephron published new progress about Resorption, animal. 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

Cao, Hao-Qiang published the artcileDirect Enamido C(sp2)-H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates, SDS of cas: 1468-83-3, the main research area is amide unsaturated vinylamide oxidative phosphonylation preparation gem diphosphonate; proton coupled electron transfer enamide phosphonylation radical relay process; unsaturated gem vinylidenediphosphonate amino preparation diphosphonylation enamide silver promoted; bisphosphonates; enamides; radical relay; silver; synthetic methods.

Gem-Diphosphonates ArC(NHCOMe):C[P(O)(OR)2]2 (Ar = substituted Ph, pyridyl, pyrrolyl, thienyl, thiazolyl) were prepared by Ag2O-promoted oxidative diphosphonylation of vinylamides CH2:CArNHCOMe with hydrophosphonates HP(O)(OR)2. Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)-H diphosphorylation. This reaction represents a rare example of realizing the challenging double C-P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.

Chemistry – A European Journal published new progress about C-P bond formation. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, SDS of cas: 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

King, Adam M. published the artcileCapillary ultra performance liquid chromatography-tandem mass spectrometry analysis of tienilic acid metabolites in urine following intravenous administration to the rat, Computed Properties of 40180-04-9, the main research area is capillary UPLC MS tienilate metabolite determination urine pharmacokinetics; Bioanalysis; Capillary UPLC; DMPK; Metabolites; Tienilic acid.

Capillary scale (100 mm × 150 μm id) UPLC/MS/MS, performed using reversed-phase gradient chromatog. on sub 2μm particles, has been successfully employed for the characterization of the metabolites of the drug tienilic acid (TA) excreted via the urine following oral administration to the rat. The capillary LC system provided a significant increase (range ∼11-33-fold) in sensitivity compared with a conventional 150 mm × 2.1 mm id UPLC system. An investigation of the effect of the injection volume and sample mass loading on the capillary column on the results obtained for both endogenous metabolites and TA was performed. This demonstrated that the injection of up to 2μL of rat urine onto the system was permitted while still providing excellent chromatog. results and robustness. Qual. anal. of the urine revealed the presence of TA itself and a total of 15 metabolites of the drug, including those resulting from biotransformations such as hydroxylation or conjugation. The capillary chromatog. system was shown to be robust, and capable of providing comprehensive drug metabolite profiles from small format urine samples such as those obtained from preclin. studies in rodents.

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences published new progress about Conjugation (bond). 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, Computed Properties of 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Yu, Pei published the artcileIdentification of volatile sulfur-containing compounds and the precursor of dimethyl sulfide in cold-pressed rapeseed oil by GC-SCD and UPLC-MS/MS, Recommanded Product: 3-Acetylthiophene, the main research area is rapeseed oil volatile sulfur containing compound dimethyl sulfide; (Methyldisulfanyl)methane (PubChemCID 12232); (Methylsulfinyl)methane (PubChem CID 679); 1,3-Thiazole (PubChemCID 9256); 1-(3-Thienyl)ethanone (PubChemCID 15116); 2-Methyl-1,3-thiazole (PubChemCID 77129); 2-[(Methylsulfanyl)methyl]furan (PubChemCID 518937); 3-(Allyldisulfanyl)-1-propene (PubChem CID 16590); 3-(Methyldisulfanyl)-1-propene (PubChemCID 62434); 3-(Methylsulfanyl)-1-propene (PubChemCID 66282); 3-(Methylthio)butyraldehyde (PubChemCID 61845); 5-Methyl-2-thiophenecarboxaldehyde (PubChemCID 61663); Bis(methylsulfanyl)methane (PubChemCID 15380); Cold-pressed rapeseed oil; Diallyltrisulfane (PubChemCID 16315); Dimethyl sulfide; Dimethyl sulfide(PubChemCID 1068); Dimethyltrisulfane (PubChemCID 19310); Methanethiol (PubChemCID 878); S-Ethylethanethioate (PubChemCID 61171); S-Methylethanethioate (PubChemCID 73750); S-Propylethanethioate (PubChemCID 61295); S-methylmethionine; S-methylmethionine (PubChemCID 458); Sulfur chemiluminescence detection; Ultra-performance liquid chromatography tandem mass-spectrometry; Volatile sulfur-containing compounds.

Volatile sulfur-containing compounds (VSCs) provide an important contribution to foods due to their special odors. In this study, VSCs in 21 cold-pressed rapeseed oils (CROs) from 9 regions in China were extracted and separated by headspace solid-phase microextraction combined with gas chromatog. coupled with sulfur chemiluminescence detection. 19 VSCs were identified by authentic standards, and the total concentration of VSCs in all CROs ranged from 49.0 to 18129μg/kg. Di-Me sulfide (DMS), with its high odor activity value (7-14574), was the most significant aroma contributor to the CROs. Furthermore, S-methylmethionine (SMM) in rapeseed was first affirmed by ultra-performance liquid chromatog.-tandem mass spectrometry and isotope quantitation. The pos. correlation coefficient between DMS and SMM was 0.793 (p < 0.05), which confirmed SMM as a crucial precursor of DMS in CROs. This study provided a theor. basis for selecting rapeseed materials by the distribution of essential VSCs and the source of DMS. Food Chemistry published new progress about Cold-press molding. 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

Mahajan, Akhil published the artcileGreen synthesis of silver nanoparticles using green alga (Chlorella vulgaris) and its application for synthesis of quinolines derivatives, Product Details of C6H6OS, the main research area is silver nanoparticle catalyst green alga quinoline derivative.

Nanoparticles were used century ago but have regained their importance in recent years being simple, ecofriendly, pollutant free, nontoxic, low-cost approach, and due good atom economy. The authors demonstrated the synthesis of Ag nanoparticles using green algae (Chlorella vulgaris) which in turn was used for synthesis of biol. important quinolines. Algal extract was prepared and treated with Ag nitrate solution for the synthesis of Ag nanoparticles. Synthesized nanoparticles were characterized with the help of anal. tools like UV, FTIR, x-ray, and SEM and used as a catalyst for the synthesis of quinolines.

Synthetic Communications published new progress about Chlorella vulgaris. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Product Details of C6H6OS.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Gerets, Helga H. J. published the artcileInvestigation of the Nrf2 Stress Response at Cellular Level to Detect Compounds Inducing Oxidative and Electrophilic Stress, Formula: C13H8Cl2O4S, the main research area is Nrf2 oxidative electrophilic stress liver injury.

Drug-induced liver injury (DILI) remains a significant reason for drug attrition and withdrawal. DILI can be caused by several mechanisms, one of these is the formation of reactive metabolites (RM) leading to oxidative and electrophilic stress. Since such event activates NF-E2-related factor-2 (Nrf2) and its downstream pathways, it seems relevant to measure Nrf2 activation. In this article, Nrf2 activation was evaluated using two approaches. First, three human hepatocytes donors and HepG2 cells were exposed to five compounds known to produce RM- and four non-RM forming compounds The expression of seven genes under the regulation of Nrf2 was measured. An index was calculated taking into account the results of the seven genes. Subsequently, the mean index for the RM-forming and the non-RM-forming compounds was calculated for each donor, and the midpoint between these two values was determined, which represents the donor-specific threshold and the compounds were classified accordingly. All three donors obtained a sensitivity of 80% (4/5) and a specificity between 75% (3/4) and 100% (4/4). HepG2 cells obtained 80% (4/5) sensitivity, but very poor specificity 0% (0/4), which makes them less suitable, compared to human hepatocytes donors, for screening of electrophilic stress. Second, the Antioxidant-Response-Element-Reporter-Cell Line, AREc32, was exposed to the same set of compounds in addition to 13 RM-forming and 5 non-RM-forming compounds Using an arbitrary cutoff of 1.5, a sensitivity of 78% (14/18) and a specificity of 88% (7/8) were obtained. Acceptable predictive values and easiness of use make the AREC32 assay more suited to investigate Nrf2 activation compared to the first approach.

Applied In Vitro Toxicology published new progress about Cell line (AREc32). 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

Chen, Jinjin published the artcileTransition-metal-free selective pyrimidines and pyridines formation from aromatic ketones, aldehydes and ammonium salts, Category: benzothiophene, the main research area is aryl methylketone arylaldehyde ammonium acetate sodium periodate tandem multicomponent; triarylpyrimidine preparation; acetophenone benzaldehyde ammonium iodide three component cyclocondensaton; triphenylpyridine preparation.

An efficient synthesis of pyrimidines and pyridines was developed from readily available aromatic ketones, aldehydes and ammonium salts under transition-metal-free conditions. In this strategy, ammonium salts were used as nitrogen sources and only water was generated as a nontoxic byproduct. A catalytic amount of NaIO4 played an important role in the selectivity control, whereas substituted pyridines were dominantly formed in its absence.

Green Chemistry published new progress about Aldol condensation. 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

Iwamura, Atsushi published the artcileCYP2C9-mediated metabolic activation of losartan detected by a highly sensitive cell-based screening assay, Application In Synthesis of 40180-04-9, the main research area is cytochrome CYP2C9 drug metabolism losartan hepatotoxicity adenovirus vector bioassay.

Drug-induced hepatotoxicity is a major problem in drug development, and reactive metabolites generated by cytochrome P 450s are suggested to be one of the causes. CYP2C9 is one of the major enzymes in hepatic drug metabolism In the present study, we developed a highly sensitive cell-based screening system for CYP2C9-mediated metabolic activation using an adenovirus vector expressing CYP2C9 (AdCYP2C9). Human hepatocarcinoma HepG2 cells infected with our constructed AdCYP2C9 for 2 days at multiplicity of infection 10 showed significantly higher diclofenac 4′-hydroxylase activity than human hepatocytes. AdCYP2C9-infected cells were treated with several hepatotoxic drugs, resulting in a significant increase in cytotoxicity by treatment with losartan, benzbromarone, and tienilic acid. Metabolic activation of losartan by CYP2C9 has never been reported, although the metabolic activations of benzbromarone and tienilic acid have been reported. To identify the reactive metabolites of losartan, the semicarbazide adducts of losartan were investigated by liquid chromatog.-tandem mass spectrometry. Two CYP2C9-specific semicarbazide adducts of losartan (S1 and S2) were detected. S2 adduct formation suggested that a reactive metabolite was produced from the aldehyde metabolite E3179, but a possible metabolite from S1 adduct formation was not produced via E3179. In conclusion, a highly sensitive cell-based assay to evaluate CYP2C9-mediated metabolic activation was established, and we found for the first time that CYP2C9 is involved in the metabolic activation of losartan. This cell-based assay system would be useful for evaluating drug-induced cytotoxicity caused by human CYP2C9.

Drug Metabolism and Disposition published new progress about Adenoviral vectors. 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

Coen, Muireann published the artcileComparative NMR-based metabonomic investigation of the metabolic phenotype associated with tienilic acid and tienilic acid isomer, COA of Formula: C13H8Cl2O4S, the main research area is NMR metabonomic investigation metabolic phenotype tienilate isomer.

An NMR-based metabonomic approach was applied to study the systems level metabolic effects of two closely related thiophene compounds, tienilic acid (TA) and tienilic acid isomer (TAI). The metabonomic data were anchored with traditional clin. chem. and histopathol. analyses. TA was removed from the market as a result of suspected immune-mediated hepatotoxicity, whereas TAI is an intrinsic hepatotoxin. Equimolar doses of TA and TAI were administered to Sprague-Dawley rats, and sampling was conducted at 2, 6, and 24 h post-treatment. Histopathol. analyses revealed development of a significant hepatic lesion 24 h post-TAI treatment with a parallel increase in plasma alanine aminotransferase (ALT) activity. In contrast, TA was not associated with the development of a hepatic lesion or an increase in plasma ALT activity. High-resolution NMR spectral metabolic profiles were generated for liver extracts, plasma, and urine at multiple time points. Multivariate statistical tools were applied to model the metabolic profiles and identify discriminatory metabolites that reflected both the adaptation to TA administration and the onset and progression of TAI-induced hepatotoxicity. TAI was shown to induce marked metabolic effects on the metabolome at all time points, with dramatic metabolic perturbations at 24 h post-treatment correlating with the histopathol. and clin. chem. evidence of a hepatic lesion. The TAI-induced metabolic perturbations provided evidence for the generation of electrophilic reactive metabolites and a significant impairment of bioenergetic metabolic pathways. TA induced early metabolic perturbations that were largely resolved by 24 h post-treatment, suggesting the reestablishment of metabolic homeostasis and the ability to adapt to the intervention, with hepatic hypotaurine potentially representing a means of assessment of hepatic adaptation. This comparative metabonomic approach enabled the discrimination of metabolic perturbations that were common to both treatments and were interpreted as nontoxic thiophene-induced perturbations. Importantly, this approach enabled the identification of temporal metabolic perturbations that were unique to TAI or TA treatment and hence were of relevance to the development of toxicity or the ability to adapt. This approach is applicable to the future study of pharmacol. and structurally similar compounds and represents a refined means of identification of biomarkers of toxicity.

Chemical Research in Toxicology published new progress about Adaptation, animal. 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

Lewis, D. F. V. published the artcileMolecular modeling of human CYP2C subfamily enzymes CYP2C9 and CYP2C19: rationalization of substrate specificity and site-directed mutagenesis experiments in the CYP2C subfamily, HPLC of Formula: 40180-04-9, the main research area is CYP2C subfamily enzyme mol modeling; cytochrome P450 2C subfamily mol modeling.

The results of mol. modeling of human CYP2C isoenzymes, CYP2C9 and CYP2C19, are reported based on an alignment with a bacterial form of the enzyme, CYP102. The three-dimensional structures of the CYP2C enzymes are consistent with known exptl. evidence from site-directed mutagenesis, antibody recognition and regiospecificity of substrate metabolism The variations in substrate specificity between CYP2C9 and CYP2CI9 can be rationalized in terms of single amino acid residue changes within the putative active site region, of which I99H appears to be the most significant.

Xenobiotica published new progress about Electrostatic force. 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, HPLC of Formula: 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem