Category: benzothiophene

Efficient one pot multi-component domino Aldol condensation-Michael addition-Suzuki coupling reaction for the highly functionalized quinolines was written by Ubba, Eethamukkala;Kumar, Y. Suneel;Dasaradhan, C.;Khan, Fazlur-Rahman Nawaz;Jeong, Euh Duck;Chung, Eun Hyuk. And the article was included in Tetrahedron Letters in 2015.Formula: C8H7BO2S This article mentions the following:

A parallel and advantageous multi-component one pot reaction has been developed utilizing domino Aldol condensation-Michael addition-Suzuki coupling approach for a variety of 2,3-disubstituted highly functionalized quinolines. The domino reactions of 2-chloro-3-formylquinolines, acetophenones, and distinctive boronic acids, were carried out utilizing PdCl₂(PPh₃)₂/tripotassium phosphate/ethanol-water system. At 80 °C they gave diversified functionalized quinolines in good yields. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Formula: C8H7BO2S).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Formula: C8H7BO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Thiophene/thiazole-benzene replacement on guanidine derivatives targeting α₂-Adrenoceptors was written by Flood, Aoife;Trujillo, Cristina;Sanchez-Sanz, Goar;Kelly, Brendan;Muguruza, Carolina;Callado, Luis F.;Rozas, Isabel. And the article was included in European Journal of Medicinal Chemistry in 2017.Reference of 5936-58-3 This article mentions the following:

Searching for improved antagonists of α₂-adrenoceptors, a thorough theor. study comparing the aromaticity of phenyl-, pyridinyl-, thiophenyl- and thiazolylguanidinium derivatives were carried out [at M06-2X/6-311++G(p,d) computational level] confirming that thiophene and thiazole were good ‘ring equivalent’ to benzene in these guanidinium systems. Based on these results, a small but chem. diverse library of guanidine derivatives were synthesized to explore the effect that the bioisosteric change has on affinity and activity at α₂-adrenoceptors in comparison with our previously studied Ph derivatives All compounds were tested for their α₂-adrenoceptor affinity and unsubstituted guanidinothiophenes displayed the strongest affinities in the same range as the Ph analogs. In the case of cycloalkyl systems, thiophenes with 6-membered rings showed the largest affinities, while for the thiazoles the 5-membered analog presented the strongest affinity. From all the compounds tested for noradrenergic activity, only one compound exhibited agonistic activity, while two compounds showed very promising antagonism of α₂-adrenoceptors. In the experiment, the researchers used many compounds, for example, 2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (cas: 5936-58-3Reference of 5936-58-3).

2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (cas: 5936-58-3) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Reference of 5936-58-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Structure-Based Optimization of a Small Molecule Antagonist of the Interaction Between WD Repeat-Containing Protein 5 (WDR5) and Mixed-Lineage Leukemia 1 (MLL1) was written by Getlik, Matthaus;Smil, David;Zepeda-Velazquez, Carlos;Bolshan, Yuri;Poda, Gennady;Wu, Hong;Dong, Aiping;Kuznetsova, Ekaterina;Marcellus, Richard;Senisterra, Guillermo;Dombrovski, Ludmila;Hajian, Taraneh;Kiyota, Taira;Schapira, Matthieu;Arrowsmith, Cheryl H.;Brown, Peter J.;Vedadi, Masoud;Al-awar, Rima. And the article was included in Journal of Medicinal Chemistry in 2016.Recommanded Product: Benzo[b]thiophen-3-ylboronic acid This article mentions the following:

WD repeat-containing protein 5 (WDR5) is an important component of the multiprotein complex essential for activating mixed-lineage leukemia 1 (MLL1). Rearrangement of the MLL1 gene is associated with onset and progression of acute myeloid and lymphoblastic leukemias, and targeting the WDR5-MLL1 interaction may result in new cancer therapeutics. Our previous work showed that binding of small mol. ligands to WDR5 can modulate its interaction with MLL1, suppressing MLL1 methyltransferase activity. Initial structure-activity relationship studies identified N-(2-(4-methylpiperazin-1-yl)-5-substituted-phenyl) benzamides as potent and selective antagonists of this protein-protein interaction. Guided by crystal structure data and supported by in silico library design, we optimized the scaffold by varying the C-1 benzamide and C-5 substituents. This allowed us to develop the first highly potent (K_disp < 100 nM) small mol. antagonists of the WDR5-MLL1 interaction and demonstrate that N-(4-(4-methylpiperazin-1-yl)-3′-(morpholinomethyl)-[1,1′-biphenyl]-3-yl)-6-oxo-4-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide 16d (OICR-9429) is a potent and selective chem. probe suitable to help dissect the biol. role of WDR5. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Recommanded Product: Benzo[b]thiophen-3-ylboronic acid).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Recommanded Product: Benzo[b]thiophen-3-ylboronic acid

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Investigations on small molecule inhibitors targeting the histone H3K4 tri-methyllysine binding PHD-finger of JmjC histone demethylases was written by Bhushan, Bhaskar;Erdmann, Alexandre;Zhang, Yijia;Belle, Roman;Johannson, Catrine;Oppermann, Udo;Hopkinson, Richard J.;Schofield, Christopher J.;Kawamura, Akane. And the article was included in Bioorganic & Medicinal Chemistry in 2018.Recommanded Product: 1195-14-8 This article mentions the following:

Plant homeodomain (PHD) finger containing proteins are important epigenetic regulators and are of interest as potential drug targets. Inspired by the amiodarone derivatives reported to inhibit the PHD finger 3 of KDM5A (KDM5A(PHD3)), a set of compounds were synthesized. Amiodarone and its derivatives were observed to weakly disrupt the interactions of a histone H3K4me3 peptide with KDM5A(PHD3). Selected amiodarone derivatives inhibited catalysis of KDM5A, but in a PHD-finger independent manner. Amiodarone derivatives also bind to H3K4me3-binding PHD-fingers from the KDM7 subfamily. Further work is required to develop potent and selective PHD finger inhibitors. In the experiment, the researchers used many compounds, for example, 2-Methylbenzo[b]thiophene (cas: 1195-14-8Recommanded Product: 1195-14-8).

2-Methylbenzo[b]thiophene (cas: 1195-14-8) belongs to benzothiophene derivatives. Benzothiophene is used as starting material for the synthesis of bioactive molecules. The core structure is a part of various pharmaceutical substances and natural products. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Recommanded Product: 1195-14-8

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Pyrrolo[1,2-a]quinoxalines from chalcones: An alternate route was written by Togiti, Uday Kumar;Shukla, Adarash Kumar;Bhattacharya, Anupam. And the article was included in Tetrahedron Letters in 2021.Application In Synthesis of 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one This article mentions the following:

The synthesis of 2,4-disubstituted pyrrolo[1,2-a]quinoxalines from chalcones is reported. The key steps used are polyphosphoric acid (PPA) assisted acyl rearrangement of the pyrrole ring and Fe catalyzed reduction-cyclization leading to 2,4-disubstituted pyrrolo[1,2-a]quinoxalines. Despite the utilization of comparatively unreactive aromatic ketones, modest to good yields were obtained. In the experiment, the researchers used many compounds, for example, 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0Application In Synthesis of 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one).

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Application In Synthesis of 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

All solid state (ASS) polymeric membrane sensor (PMS) for the monitoring of nanomolar nickel concentration was written by Ganjali, Mohammad Reza;Alahdadi, Iraj;Aghazadeh, Mustafa;Pourbasheer, Eslam. And the article was included in International Journal of Electrochemical Science in 2015.Computed Properties of C26H26N2O2S This article mentions the following:

A nickel(II) selective all-solid-state PVC membrane sensor (ASS-PMS) has been designed and constructed for the monitoring of nanomolar nickel(II) concentrations in various samples. The applicability of the sensor to real samples was proved through its use for the anal. of the target ion in waste water samples. The all solid state support and transducer was build through coating a nickel wire with a composite of graphite powder and an epoxy resin, and next it was coated with a nickel selective PVC membrane, with the optimal composition of 33% of PVC, 57% of Nitrobenzene, 2% RTIL (1-n-butyl-3-methylimidazolium hexafluorophosphate), 3% of KpClTPB, and 5% of ionophore L. The potential response of the ASS-PMS change with the concentration of the target ion at a slope of 29.5 ± 0.3 mV/decade, which is indicative of a Nernstian behavior, and was linear in the concentration range of 1.0 × 10-8 to 1.0 × 10-3 mol L-1 of the nickel(II), reaching a lower detection limit as low as 5.0 × 10-9 mol L-1. The response of the ASS-PMS was found to be almost independent from interference from different conventional ionic species. The ASS-PMS was successfully applied to the potentiometric determination of nickel(II) concentrations in ions electroplating waste water samples. In the experiment, the researchers used many compounds, for example, 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene (cas: 7128-64-5Computed Properties of C26H26N2O2S).

2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene (cas: 7128-64-5) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Computed Properties of C26H26N2O2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroindolation of cis-Methindolylstyrenes To Access Tetrahydrobenzo[cd]indoles was written by Cai, Xiao;Tohti, Anargul;Ramirez, Cristian;Harb, Hassan;Fettinger, James C.;Hratchian, Hrant P.;Stokes, Benjamin J.. And the article was included in Organic Letters in 2019.SDS of cas: 5118-13-8 This article mentions the following:

Readily prepared cis-β-(α’,α’-dimethyl)-4′-methindolylstyrenes undergo acid-catalyzed intramol. hydroindolation to afford tetrahydrobenzo[cd]indoles. Our exptl. and computational investigations suggest that dispersive interactions between the indole and styrene preorganize substrates such that 6-membered ring formation is preferred, apparently via concerted protonation and C-C bond formation. When dispersion is attenuated (by a substituent or heteroatom), regioselectivity erodes and competing oligomerization predominates for cis substrates. Similarly, all trans-configured substrates that we evaluated failed to cyclize efficiently. In the experiment, the researchers used many compounds, for example, 4-Bromobenzo[b]thiophene (cas: 5118-13-8SDS of cas: 5118-13-8).

4-Bromobenzo[b]thiophene (cas: 5118-13-8) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.SDS of cas: 5118-13-8

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

χ-Shaped Bis(areno)-1,4-dihydropyrrolo[3,2-b]pyrroles Generated by Oxidative Aromatic Coupling was written by Krzeszewski, Maciej;Gryko, Daniel T.. And the article was included in Journal of Organic Chemistry in 2015.Product Details of 113893-08-6 This article mentions the following:

A synthesis of dihydropyrrolo[3,2-b]pyrroles fused with two peripheral arenes or heterocyclic units was realized through the concise route. These nearly planar compounds were prepared starting from assembling the central core via condensation of 2-aryl or 2-heteroarylbenzaldehydes with aromatic amines and diacetyl, followed by double intramol. oxidative aromatic coupling. This two-step procedure afforded the desired products in overall yields of 5-36%, and it tolerates structural diversity of starting materials. All the final dyes exhibit strong blue fluorescence in solution In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Product Details of 113893-08-6).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene is used as starting material for the synthesis of bioactive molecules. The core structure is a part of various pharmaceutical substances and natural products. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Product Details of 113893-08-6

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Axially chiral 3,3′-bi(1-benzothiophene)-2,2′-dicarboxylic acid and its derivatives was written by Mezlova, Marie;Petrickova, Hana;Malon, Petr;Kozmik, Vaclav;Svoboda, Jiri. And the article was included in Collection of Czechoslovak Chemical Communications in 2003.Reference of 19492-99-0 This article mentions the following:

Ullmann dimerization of substituted Me 3-X-1-benzothiophene-2-carboxylates (X = Cl, Br) gave rise to the corresponding dimeric 3,3′-bi(1-benzothiophene) esters. Resolution of the title acid by fractional crystallization of its mono- and bisquininium salt afforded pure (R)- and (S)-enantiomers, the optical purity and absolute configuration of which was confirmed by CD spectrometry and by X-ray crystallog. Ullmann dimerization of some of the chiral oxazolines proceeded without any diastereodifferentiation. Reduction of some of the (R)- and (S)-products afforded the corresponding (R)- and (S)-diols, which served as chiral ligands in a model enantioselective reduction of acetophenone. (R)- and (S)-1-phenylethan-1-ol were formed. In the experiment, the researchers used many compounds, for example, Methyl 5-methoxybenzo[b]thiophene-2-carboxylate (cas: 19492-99-0Reference of 19492-99-0).

Methyl 5-methoxybenzo[b]thiophene-2-carboxylate (cas: 19492-99-0) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Reference of 19492-99-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Desulfurization of benzo- and dibenzothiophenes with nickel boride was written by Back, Thomas G.;Yang, Kexin;Krouse, H. Roy. And the article was included in Journal of Organic Chemistry in 1992.Application In Synthesis of Dibenzo[b,d]thiophen-3-amine This article mentions the following:

Nickel boride, prepared from the reduction of nickel chloride hexahydrate with sodium borohydride in methanol-tetrahydrofuran, reduces benzothiophenes to alkylbenzenes and dibenzothiophenes to biphenyls. The reaction is rapid at or below room temperature and does not require protection from the atm. Best results are obtained when the nickel boride is generated in situ in the presence of the sulfur compound Hydroxyl, carboxyl, ester, and amino groups are unaffected while chloro, bromo, and nitro substituents are also reduced under these conditions. A short-lived intermediate, possibly a nickel hydride species, appears to be required in the desulfurization. Complexation of the substrate to the nickel boride surface, followed by stepwise reduction of the two CS bonds, occurs. The faster disappearance of dibenzothiophene containing the lighter ³²S isotope compared to that with ³⁴S [k(³²S)/k(³⁴S) = 1.005 to 1.006] suggests that CS bond cleavage is the rate determining step. In the experiment, the researchers used many compounds, for example, Dibenzo[b,d]thiophen-3-amine (cas: 25288-76-0Application In Synthesis of Dibenzo[b,d]thiophen-3-amine).

Dibenzo[b,d]thiophen-3-amine (cas: 25288-76-0) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Application In Synthesis of Dibenzo[b,d]thiophen-3-amine

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem