Heterocyclic Building Blocks-Benzothiophene

Lecoeur, S. published the artcileTienilic acid-induced autoimmune hepatitis: anti-liver and -kidney microsomal type 2 autoantibodies recognize a three-site conformational epitope on cytochrome P4502C9, Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is autoimmune hepatitis tienilic acid cytochrome P4502C9.

Tienilic acid-induced hepatitis is characterized by the presence of anti-liver and -kidney microsomal (anti-LKM2) autoantibodies in patient sera. Cytochrome P 4502C9 (CYP2C9), involved in the metabolism of tienilic acid, was shown to be a target for tienilic acid-reactive metabolites and for autoantibodies. To further investigate the relationship between drug metabolism and the pathogenesis of this drug-induced autoimmune disease, the specificity of anti-LKM2 autoantibodies toward CYP2C9 was first determined, and the antigen sites on CYP2C9 were localized. By constructing several deletion mutants derived from CYP2C9 cDNA and by probing the corresponding proteins with different anti-LKM2 sera, we defined three regions (amino acids 314-322, 345-356, and 439-455); they interacted to form a major conformational autoantibody binding site. This binding site was immunoreactive with 100% of sera and allowed removal of the entire reactivity of the sera tested by immunoblotting. Epitope mapping studies have been performed for CYP2D6, CYP17, CYP21A2, and, recently, CYP3A. Those data were compared with the results obtained in the current study with CYP2C9 in an attempt to elucidate one of the mechanisms by which CYP becomes immunogenic.

Molecular Pharmacology published new progress about Autoimmune hepatitis. 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

Vicente-Carrillo, A. published the artcileBoar spermatozoa successfully predict mitochondrial modes of toxicity: Implications for drug toxicity testing and the 3R principles, Related Products of benzothiophene, the main research area is boar sperm mitochondria toxicity drug testing; Boar; Drug; Mitochondria; Motility; Sperm; Toxicity.

Replacement of animal testing by in vitro methods (3-R principles) requires validation of suitable cell models, preferably obtained non-invasively, defying traditional use of explants. Ejaculated spermatozoa are highly dependent on mitochondrial production and consumption of ATP for their metabolism, including motility display, thus becoming a suitable model for capturing multiple modes of action of drugs and other chems. acting via mitochondrial disturbance. In this study, a hypothesis was tested that the boar spermatozoon is a suitable cell type for toxicity assessment, providing a protocol for 3R-replacement of animals for research and drug-testing. Boar sperm kinetics was challenged with a wide variety of known frank mito-toxic chems. with previously shown mitochondrial effects, using a semi-automated motility analyzer allied with real-time fluorescent probing of mitochondrial potential (MitoTracker & JC-1). Output of this sperm assay (obtained after 30 min) was compared to cell viability (ATP-content, data obtained after 24-48 h) of a hepatome-cell line (HepG2). Results of compound effects significantly correlated for all sperm variables and for most variables in (HepG2). Dose-dependent decreases of relative ATP content in HepG2 cells correlated to sperm speed (r = 0.559) and proportions of motile (r = 0.55) or progressively motile (r = 0.53) spermatozoa. The significance of the study relies on the objectivity of computerized testing of sperm motility inhibition which is comparable albeit of faster output than somatic cell culture models. Sperm suspensions, easily and painlessly obtained from breeding boars, are confirmed as suitable biosensors for preclin. toxicol. screening and ranking of lead compounds in the drug development processes.

Toxicology In Vitro published new progress about Antimicrobial agents. 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

Murcia-Soler, Miguel published the artcileDiscrimination and selection of new potential antibacterial compounds using simple topological descriptors, Product Details of C13H8Cl2O4S, the main research area is antibacterial topol structure activity relationship.

The aim of the work was to discriminate between antibacterial and non-antibacterial drugs by topol. methods and to select new potential antibacterial agents from among new structures. The method used for antibacterial activity selection was a linear discriminant anal. (LDA). It is possible to obtain a QSAR interpretation of the information contained in the discriminant function. We make use of the pharmacol. distribution diagrams (PDDs) as a visualizing technique for the identification and selection of new antibacterial agents.

Journal of Molecular Graphics & Modelling published new progress about Antibacterial agents. 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, Product Details of C13H8Cl2O4S.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Pacitto, Stephanie R. published the artcileChanges in gene expression induced by tienilic acid and sulfamethoxazole: testing the danger hypothesis, HPLC of Formula: 40180-04-9, the main research area is tienilic acid sulfamethoxazole gene expression microarray idiosyncratic drug toxicity; cell stress tienilate sulfamethoxazole idiosyncratic drug toxicity.

Tienilic acid (TA) was withdrawn due to idiosyncratic hepatotoxicity. Two hypotheses for the mechanisms of idiosyncratic reactions are the hapten and danger hypotheses, which are not mutually exclusive. Both human CYP 2C9 and rat CYP 2C11 metabolize TA to a reactive metabolite that was reported to bind exclusively to these enzymes. TA-Induced liver toxicity is associated with antibodies against CYP 2C9, thus TA appears to act as a hapten. However, if the binding were limited to CYP 2C, it is unlikely that this would lead to significant cell stress. If TA does not cause cell stress it would suggest that acting as a hapten is sufficient to induce an idiosyncratic reaction. To test whether TA can cause cell stress rats were dosed with TA and hepatic gene expression was profiled at 6 and 24 h after drug administration. TA induced changes in genes involved in oxidative stress (aldo-keto reductase, glutathione-S-transferase, thioredoxin reductase, epoxide hydrolase), inflammation (IL-1β, interferon regulatory factor 1, macrophage stimulating protein 1), cytotoxicity (caspase-12), and liver regeneration (p27Kip1, DUSP6, serine dehydratase, spectrin βII, inhibin βA). These data support the hypothesis that danger signals in the form of cell-stress may be involved in initiating the immune response observed in TA-induced toxicity. In sep. experiments, the authors examined the changes in gene expression induced in mice by sulfamethoxazole, which also causes idiosyncratic reactions. Sulfamethoxazole is an aromatic amine, and aromatic amines in general are associated with idiosyncratic drug reactions. They form reactive metabolites that both act as electrophiles and can redox cycle; therefore, it was assumed that sulfamethoxazole would cause some type of cell stress, the only question was what changes in mRNA expression would occur. In contrast to expectations, no changes induced by sulfamethoxazole could easily be interpreted as a danger signal. These data are presented together because they are the opposite of the expected results and convey a complex story.

Journal of Immunotoxicology published new progress about Antibacterial agents. 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

Tighadouini, Said published the artcileSynthesis, Biochemical Characterization, and Theoretical Studies of Novel β-Keto-enol Pyridine and Furan Derivatives as Potent Antifungal Agents, Synthetic Route of 1468-83-3, the main research area is keto enol pyridine furan antifungal antibacterial mol docking dynamic.

In the present study, we report the design and synthesis of new derivatives of the β-keto-enol grafted on pyridine and furan moieties (L1-L11). Structures of compounds were fully confirmed by Fourier transform IR spectroscopy (FT-IR), 1H NMR, 13C NMR, electrospray ionization/liquid chromatog.-mass spectrometry (ESI/LC-MS), and elemental anal. The compounds were screened for antifungal and antibacterial activities (Escherichia coli, Bacillus subtilis, and Micrococcus luteus). In vitro evaluation showed significant fungicidal activity for I, II, and III against fungal strains (Fusarium oxysporum f.sp albedinis) compared to the reference standard Especially, the exceptional activity has been demonstrated for I with IC50 = 12.83μg/mL. This compound and the reference benomyl mol. also showed a correlation between exptl. antifungal activity and theor. predictions by Petra/Osiris/Molinspiration (POM) calculations and mol. coupling against the Fgb1 protein. The highest inhibition of bacterial growth for I is due to its strongest binding to the target protein. This report may stimulate the further synthesis of examples of this substance class for the development of new drugs.

ACS Omega published new progress about Antibacterial agents. 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

Tighadouini, Said published the artcileNovel β-keto-enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies, Synthetic Route of 1468-83-3, the main research area is antibacterial antifungal crystal structure mol docking pharmacol SAR DFT; keto enol pyrazole derivative preparation.

A new family of promising inhibitors bearing β-keto-enol functionality with greatly improved pharmacophore properties has been prepared Herein, a series of novel derivatives of β-keto-enol group embedded with pyrazolic moiety has been designed and synthesized via a one-step procedure using mixed Claisen condensation in the attempt to develop potential antifungal agents. The structures of the synthesized compounds were confirmed by elemental anal., FT-IR, ESI/LC-MS, and 1H and 13C NMR. In addition, X-ray diffraction anal. (XRD) was used to determine the single crystal structure of compound I. All of the new compounds have been evaluated for their in vitro antifungal and antibacterial activities. Interestingly, the results indicate that most of the compounds display notable antifungal activity close to that of the benomyl fungicide taken as the standard drug. For the most active compound and for benomyl, a correlation has been evidenced between the exptl. antifungal activity and the theor. predictions by DFT calculations and mol. docking against Fgb1 protein.

Journal of Chemical Information and Modeling published new progress about Antibacterial agents. 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

Almohaywi, Basmah published the artcileDihydropyrrolones as bacterial quorum sensing inhibitors, Safety of 3-Acetylthiophene, the main research area is dihydropyyrolone preparation bacterial quorum sensing inhibitor SAR docking; Biofilm inhibition; Dihydropyrrolone; P. aeruginosa; Quorum sensing.

A range of dihydropyrrolone (DHP) analogs were synthesized via the lactone-lactam conversion of lactone intermediates. The synthesized compounds were tested for their ability to inhibit QS, biofilm formation and bacterial growth of Pseudomonas aeruginosa. The compounds were also docked into a LasR crystal structure to rationalize the observed structure-activity relationships. The most active compound identified in this study was 4-(4-bromophenyl)-5-methylene-1,5-dihydro-2H-pyrrol-2-one which showed 63.1% QS inhibition of at 31.25 μM and 60% biofilm reduction at 250 μM with only moderate toxicity towards bacterial cell growth.

Bioorganic & Medicinal Chemistry Letters published new progress about Antibacterial agents. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Safety of 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Wang, Chunlian published the artcileCopper-catalyzed three-component N-alkylation of quinazolinones and azoles, Recommanded Product: 3-Acetylthiophene, the main research area is alkylated quinazolinone preparation; quinazolinone methyl ketone dimethylpropionamide alkylation coupling copper catalyst; azole alkylated preparation; methyl ketone azole dimethylpropionamide alkylation coupling copper catalyst.

Synthesis of N-alkylated heterocycles such as quinazolinones I [R = H, 7-Cl, 7-F, etc.; R1 = Ph, 4-MeC6H4, 4-FC6H4, etc.] and azoles II [R1 = H, 4-Me, 4-OMe, etc.; n = 0, 1, 2, 3; X = N, CH, Y = N = CH, Z = CH, N; R2 = H, 4-EtOC6H4, cyclopropyl, etc.] via Cu-catalyzed three-component N-alkylation coupling reaction of N-heteroarenes with Me ketones and DMPA as a carbon source was developed. Using Me ketones as alkylation reagents and DMPA (N,N’-dimethylpropionamide) as a carbon source, the reaction proceeded smoothly under the Cu-based oxidative system and led to a series of functionalized N-heterocycles including 4-quinazolinones, triazoles and pyrazoles.

Organic & Biomolecular Chemistry published new progress about Alkylation catalysts. 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

Shinde, Suraj R. published the artcileDiscovery of oxazole-dehydrozingerone based hybrid molecules as potential anti-tubercular agents and their docking for Mtb DNA gyrase, Recommanded Product: 3-Acetylthiophene, the main research area is oxazole dehydrozingerone hybrid preparation antitubercular docking Mtb DNA gyrase.

The oxazole-dehydrozingerone hybrid mols. I (R = 4-Br, 4-Cl, 3-F, etc.) and oxazole-dehydrozingerone-thiophene derivatives were synthesized via cyclization, coupling and aldol condensation reactions. Synthesized compounds were screened against Mycobacterium tuberculosis H37Rv, MDR, and XDR strains. Compound I (R = 4-NO2) showed potential activity of 6.25μg/mL against H37Rv, while compound I (R = 3-NO2) exhibited potential activity of 12.5μg/mL. For the XDR strain, structure I (R = 4-Br, 4-Cl) demonstrated moderate efficiency of 12.5μg/mL. All of the synthesized mols. were tested in comparison with a standard drug. Computational docking studies were performed for the active compound I (R = 4-NO2) against the enzyme Mtb DNA Gyrase. The outcomes of the presented research will broadly help to the researchers working on developing antituberculosis drugs.

Results in Chemistry published new progress about Microwave irradiation. 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

Huang, Chun published the artcileDirect Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- and Azide-Free Conditions, Category: benzothiophene, the main research area is aryl triazole preparation; methyl ketone para toluenesulfonyl hydrazine aminopyridinium iodide cyclization iodine.

Authors herein report an iodine-mediated formal [2 + 2 + 1] cyclization of Me ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved using p-toluenesulfonyl hydrazines and 1-aminopyridinium iodide as azide surrogates, providing a novel route to NH-1,2,3-triazoles. Furthermore, this approach provides rapid and practical access to potent inhibitors of indoleamine 2,3-dioxygenase (IDO).

Journal of Organic Chemistry published new progress about Cyclization ([2+2+1]). 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