Heterocyclic Building Blocks-Benzothiophene

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

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 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

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 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

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 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 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 September 5, 1984, Ward, Robert William; Smith, Stephen Allan; Markwell, Roger Edward published a patent.Related Products of 16296-68-7 The title of the patent was Benzofuran- and benzothiophenecarboxylic acid derivatives. And the patent contained the following:

The title compounds I [X = O, S, SO, SO2, X1 = CH2; X = CH2, X1 = O; R = Ph, alkylphenyl, alkoxyphenyl, CF3C6H4, BrC6H4, ClC6H4, FC6H4, pyrrolyl, N-alkylpyrrolyl, furyl, thienyl, (un)substituted by Me, Cl, or Br; R1,R3 = H, alkyl; R2 = H, F, Cl, Br; R4 = H, alkyl] were prepared Thus, II (R2 = Br, R4 = R5 = H) was prepared by ring contraction of 6-bromo-4-chromanone with Tl(NO3)3, esterified, and subjected to Friedel-Crafts acylation with BzCl to give II (R2 = Br, R4 = Et, R5 = Bz) which was debrominated and saponified to II (R2 = R4 = H, R5 = Bz, III). At 5 mg/kg orally the phenylquinone writhing test in mice III gave analgesia in 90% of the animals. 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 benzofurancarboxylate preparation analgesic, benzothiophenecarboxylate, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenothiophenes and other aspects.Related Products of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On June 15, 2011, Capek, Petr; Zhang, Yan; Barlow, Deborah J.; Houseknecht, Karen L.; Smith, Garry R.; Dickerson, Tobin J. published an article.Recommanded Product: 16296-68-7 The title of the article was Enhancing the Pharmacokinetic Properties of Botulinum Neurotoxin Serotype A Protease Inhibitors through Rational Design. And the article contained the following:

Botulinum neurotoxin (BoNT), the etiol. agent that causes the neuroparalytic disease botulism, has become a highly studied drug target in light of the potential abuse of this toxin as a weapon of bioterrorism. In particular, small mol. inhibitors of the light chain metalloprotease of BoNT serotype A have received significant attention and a number of small mol. and biol. inhibitors have been reported. However, all small mols. reported have been identified from either primary screens or medicinal chem. follow-up studies, and the pharmacokinetic profiles of these compounds have not been addressed. In this study, we have removed the pharmacol. liabilities of one of the best compounds reported to date, 2,4-dichlorocinnamate hydroxamic acid, and in the process uncovered a related class of benzothiophene hydroxamic acids that are significantly more potent inhibitors of the BoNT/A light chain, while also possessing greatly improved ADME properties, with the best compound showing the most potent inhibition of BoNT/A light chain reported (Ki = 77 nM). Using a strategy of incorporating traditional drug development filters early into the discovery process, potential liabilities in BoNT/A lead compounds have been illuminated and removed, clearing the path for advancement into further pharmacol. optimization and in vivo efficacy testing. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Recommanded Product: 16296-68-7

The Article related to botulinum neurotoxin serotype a protease inhibitor chlorocinnamate benzothiophene hydroxamate, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenothiophenes and other aspects.Recommanded Product: 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem