Category: benzothiophene

On August 26, 2015, Chen, Shuhui; Zhu, Wenyuan; Wang, Jianfei; Li, Jian; Wei, Yuquan; Yu, Luoting; Tao, Xin published a patent.Reference of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid The title of the patent was Thiophene-imidazole derivatives as hepatitis c virus inhibitors and their preparation, pharmaceutical compositions and use in the treatment of chronic hepatitis C virus infection. And the patent contained the following:

The invention discloses a series of thiophene or its variant derivative and composition as hepatitis C virus inhibitor, and relating to its application in preparation chronic HCV infection treatment medicine.In particular it relates to the series compound as NS5A inhibitor and composition thereof and pharmaceutical applications. Disclosed is thiophene-imidazole derivatives, e.g., I, as hepatitis C virus (HCV) inhibitors or variant derivatives thereof and compositions thereof. The invention further relates to the application in preparing chronic hepatitis C virus infection drugs. Particularly, the invention relates to a series of compounds used as NS5A inhibitors and compositions thereof and uses thereof for drug preparation Compound I was prepared by using cyclization, cross-coupling and condensation as the key steps. All the invention compounds were evaluated for their hepatitis c virus and NS5A inhibitory activity. From the assay, it was determined that example compound I exhibited the EC50 and CC50 values of 0.001 – 0.1 nM and > 10 nM against HCV 1b. The experimental process involved the reaction of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid(cas: 188240-63-3).Reference of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid

The Article related to thiophene imidazole preparation ns5a inhibitor treatment chronic hepatitis c, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Reference of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On August 27, 2015, Chen, Shuhui; Zhu, Wenyuan; Wang, Jianfei; Li, Jian; Wei, Yuquan; Yu, Luoting; Tao, Xin published a patent.COA of Formula: C9H9BrO2S The title of the patent was Thiophene-imidazole derivatives as hepatitis c virus inhibitors and their preparation, pharmaceutical compositions and use in the treatment of chronic hepatitis C virus infection. And the patent contained the following:

Disclosed is thiophene-imidazole derivatives, e.g., I, as hepatitis C virus (HCV) inhibitors or variant derivatives thereof and compositions thereof. The invention further relates to the application in preparing chronic hepatitis C virus infection drugs. Particularly, the invention relates to a series of compounds used as NS5A inhibitors and compositions thereof and uses thereof for drug preparation Compound I was prepared by using cyclization, cross-coupling and condensation as the key steps. All the invention compounds were evaluated for their hepatitis c virus and NS5A inhibitory activity. From the assay, it was determined that example compound I exhibited the EC50 and CC50 values of 0.001 – 0.1 nM and > 10 nM against HCV 1b. The experimental process involved the reaction of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid(cas: 188240-63-3).COA of Formula: C9H9BrO2S

The Article related to thiophene imidazole preparation ns5a inhibitor treatment chronic hepatitis c, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.COA of Formula: C9H9BrO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On February 13, 2020, Ngu, Khehyong published a patent.Reference of 5-Chlorobenzo[b]thiophene-3-carbaldehyde The title of the patent was Benzimidazoles as inhibitors of PAD enzymes and their preparation. And the patent contained the following:

The invention provides compounds of formula I or a pharmaceutically acceptable salt thereof, useful as inhibitors of PAD4, compositions thereof, and methods of treating PAD4-related disorders. Compounds of formula I wherein ring A is 4- to 15-membered heterocyclyl; B is (un)substituted indolyl, (un)substituted azaindolyl, (un)substituted benzothienyl and (un)substituted phenyl; R1 is substituted C3-6 cycloalkyl, (CH2)2-4R5a, substituted (CH2)1-4-C3-6 cycloalkyl, etc.; R3 is H, F, Cl, Br, etc.; R8 is independently H, F, Cl, CN, etc.; R5a is CONH2 and derivatives, NH2 and derivatives, NHCO2H and derivatives, etc.; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their PAD4 inhibitory activity. From the assay, it was determined that compound II exhibited IC50 value of 0.014μM. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Reference of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

The Article related to benzimidazole preparation pad inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Reference of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On December 4, 2008, Geneste, Herve; Sauer, Daryl; Braje, Wilfried; Amberg, Wilhelm; Mezler, Mario; Bakker, Margaretha Henrica Maria published a patent.Related Products of 16296-68-7 The title of the patent was Preparation of heterocyclic compounds, in particular pyrazole derivatives as positive modulators of metabotropic glutamate receptor 2 (mGlu2 receptor). And the patent contained the following:

Title compounds I [X = O, S, S(O), S(O)2, NH, NHC(O), NRx or a chem. bond; Rx = (un)substituted alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, Ph, 5- or 6-membered heteroaryl, etc.; Y = O, S, S(O), S(O)2, NH, NRx, (un)substituted O-phenylene, S-phenylene, NH-phenylene, or a chem. bond, A = alkylene; Ar = Ph or 5- or 6-membered heteroaryl; R1 = (un)substituted alkyl, alkoxy, haloalkyl, haloalkoxy, (un)substituted cycloalkyl, cycloalkyloxy, etc.; R2 = H, CN, OH, halo, (un)substituted alkyl, cycloalkyl, haloalkyl, alkoxy or haloalkoxy, or R1 and R2 may together with adjacent carbon atom which they bound form a (un)substituted 5- or 6-membered heterocyclic ring fused to the benzene ring; R3 = H, halo, (un)substituted alkyl, haloalkyl, alkoxy or haloalkoxy or (un)substituted cycloalkyl; Het = (un)substituted 5- or 6-membered (un)saturated or aromatic heterocycle], and their pharmaceutically acceptable salts or tautomers, are prepared and disclosed as pos. modulators of metabotropic glutamate receptor. Thus, e.g., II was prepared by reductive amination of 3-(thiophen-2-yl)-1H-pyrazole-4-carboxaldehyde with 1-(4-aminophenyl)butan-1-one. Selected compounds of the invention had activity in potentiating the mGlu2 receptor in the FLIPR assay, generally with an EC50 of < 10 μM, e.g., II showed EC50 value of < 1 μM as potentiator of mGlu2 receptor. The invention also relates to the use of these compounds for preparing a pharmaceutical composition and to a method of treating a medical disorder, selected from neurol. and psychiatric disorders associated with glutamate dysfunction. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Related Products of 16296-68-7

The Article related to pyrazole derivative preparation metabotropic glutamate mglu2 receptor modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Related Products of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Brabander, H. J. published an article in 1973, the title of the article was Synthesis of benzo[b]thiophene-3-carboxaldehydes and -3-carboxylic acids by light catalyzed NBS [N-bromosuccinimide] bromination of 3-methylbenzo[b]thiophenes.Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde And the article contains the following content:

The benzo[b]thiophene I (R = Me, R1 = Cl) was brominated with NBS to give a mixture of brominated compounds, which were hydrolyzed with 10% Na2CO3 to give 88% I (R = CHO, R1 = Cl) and 2-bromo-5- chlorobenzo[b]thiophene-3-carboxaldehyde (94:2:5). I (R = CHO, R1 = Cl) was brominated with NBS to give I (R = CO2H, R1 = Cl). I (R = CO2H, R1 = F) was similarly prepared The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde

The Article related to benzothiophenecarboxylic acid chloro, benzothiophene methyl bromination, bromination methylbenzothiophene, Heterocyclic Compounds (One Hetero Atom): Thiophenes and other aspects.Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On May 6, 2021, Zhang, Yang; Wu, Wentao; Zhu, Wenyuan; Chen, Shuhui published a patent.Safety of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid The title of the patent was Thiophene derivatives as xanthine oxidase inhibitors and application thereof. And the patent contained the following:

A class of xanthine oxidase (XO) inhibitors, and application thereof in the preparation of drugs for treating XO-related diseases. Specifically disclosed is a compound represented by formula I (R1 is independently selected from H, halide, OH, NH2, CN, etc.; n = 0, 1, 2, 3, or 4; R2 is selected from H, halide, OH, NH2 or CN; cyclic A is selected from C5-C6 cycloalkane or heterocylocalkane group) and a pharmaceutically acceptable salt thereof. For example, compound II is prepared by a multi-step synthesis starting from benzothiophene compound (CAS Number 2105532-70-3). The experimental process involved the reaction of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid(cas: 188240-63-3).Safety of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid

The Article related to thiophene derivative xanthine oxidase inhibitor drug disease, Heterocyclic Compounds (One Hetero Atom): Thiophenes and other aspects.Safety of 3-Bromo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On June 22, 2017, Violin, Jonathan D.; Soergel, David G. published a patent.Electric Literature of 16296-68-7 The title of the patent was Preparation of opioid receptor ligands useful in combination with cytochrome P450 inhibitors for treatment of pain. And the patent contained the following:

This application describes compounds of formula I as opioid receptor ligands, and compositions comprising I in combination with cytochrome P 450 inhibitors, useful for the treatment of pain and pain-related disorders. Claimed is a pharmaceutical composition comprising I or a pharmaceutically salt of I [wherein R21 and R22 independently = H or CH3; D1 = (un)substituted aryl; B3 = H or (un)substituted alkyl; B5 = (un)substituted (hetero)aryl] and at least one CYP2D6 inhibitor and CYP3A4 inhibitor; and a pharmaceutically acceptable carrier. Example compound (R)-II was prepared from the reaction of benzaldehyde with 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine in the presence of CH2Cl2 forming the corresponding imine which underwent reduction by NaBH4 affording the desired compound in 92% yield. Candidate compounds of I were evaluated for antinociceptive activity using an in vivo mouse model and hot plate assay from which (R)-II exhibited demonstrated 100% maximal possible effect at a dose of 10 mg/kg. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Electric Literature of 16296-68-7

The Article related to opioid receptor ligand preparation cytochrome p450 inhibitor combination pain, Heterocyclic Compounds (One Hetero Atom): Pyrans and other aspects.Electric Literature of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On May 10, 2012, Robertson, Mark J.; Hadzic, Gordana; Ambrus, Joseph; Pome, D. Yuri; Hyde, Emily; Whiting, Ainslie; Mariana, Anna; von Kleist, Lisa; Chau, Ngoc; Haucke, Volker; Robinson, Phillip J.; McCluskey, Adam published an article.Quality Control of 5-Chlorobenzo[b]thiophene-3-carbaldehyde The title of the article was The Rhodadyns, a New Class of Small Molecule Inhibitors of Dynamin GTPase Activity. And the article contained the following:

Six focused rhodanine-based libraries, 60 compounds in total, were synthesized and evaluated as potential dynamin I GTPase inhibitors. Twenty-six were more potent than the lead compound with 13 returning IC50 values ≤10 μM, making the Rhodadyn series among the most active dynamin inhibitors reported. Two analogs were highly effective at blocking receptor-mediated endocytosis: C10 and D10 (I) with IC50(RME) = 7.0 ± 2.2 and 5.9 ± 1.0 μM, resp. These compounds are equipotent with the best reported in-cell dynamin inhibitors. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Quality Control of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

The Article related to dynamin gtpase inhibitor rhodanine analog preparation sar, knoevengal condensation, dynamin inhibition, rhodanine, Pharmacology: Structure-Activity and other aspects.Quality Control of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Nanostructured N doped TiO2 efficient stable catalyst for Kabachnik-Fields reaction under microwave irradiation》 was written by Kunde, Sachin P.; Kanade, Kaluram G.; Karale, Bhausaheb K.; Akolkar, Hemant N.; Arbuj, Sudhir S.; Randhavane, Pratibha V.; Shinde, Santosh T.; Shaikh, Mubarak H.; Kulkarni, Aniruddha K.. Reference of 1-Thiophen-2-yl-ethanone And the article was included in RSC Advances in 2020. The article conveys some information:

Herein, we report nitrogen-doped TiO2 (N-TiO2) solid-acid nanocatalysts with heterogeneous structure employed for the solvent-free synthesis of α-aminophosphonates through Kabachnik-Fields reaction. N-TiO2 were synthesized by direct amination using triethylamine as a source of nitrogen at low temperature and optimized by varying the volume ratios of TiCl4, methanol, water, and triethylamine, under identical conditions. An X-ray diffraction (XRD) study showed the formation of a rutile phase and the crystalline size is 10 nm. The nanostructural features of N-TiO2 were examined by HR-TEM anal., which showed they had rod-like morphol. with a diameter of 7 to 10 nm. Diffuse reflectance spectra show the extended absorbance in the visible region with a narrowing in the band gap of 2.85 eV, and the high resolution XPS spectrum of the N 1s region confirmed successful doping of N in the TiO2 lattice. More significantly, we found that as-synthesized N-TiO2 showed significantly higher catalytic activity than com. available TiO2 for the synthesis of a novel series of α-amino phosphonates via Kabachnik-Fields reaction under microwave irradiation conditions. The improved catalytic activity is due to the presence of strong and Bronsted acid sites on a porous nanorod surface. This work signifies N-TiO2 is an efficient stable catalyst for the synthesis of α-aminophosphonate derivatives In the experimental materials used by the author, we found 1-Thiophen-2-yl-ethanone(cas: 88-15-3Reference of 1-Thiophen-2-yl-ethanone)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Reference of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME》 was written by Zhao, Xinxin; Li, Bing; Xia, Wujiong. Product Details of 88-15-3This research focused onvisible light hydroacylation diacylation alkene nickel chloride glyme; ketone synthesis; dicarbonyl compound synthesis. The article conveys some information:

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME. In the part of experimental materials, we found many familiar compounds, such as 1-Thiophen-2-yl-ethanone(cas: 88-15-3Product Details of 88-15-3)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Product Details of 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem