Category: 16296-68-7

El Shanta, M. S.; Scrowston, R. M. published an article in 1967, the title of the article was Preparation and properties of some 3-acetyl- and 3-formyl-5-halobenzo[b]thiophenes.Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde And the article contains the following content:

5-Chloro- and 5-bromobenzo[b]thiophene-3-carboxaldehydes (I) (X = Cl and Br) were prepared from the corresponding 3-bromomethyl compound either by the Sommelet reaction (65%) or by the Kroehnke reaction (30% yield). They had the usual properties of an aromatic aldehyde; in particular, they underwent the Doebner reaction with malonic acid, and formed crystalline condensation products with rhodanine. Friedel-Crafts acetylation of 5-chloro- or 5-bromobenzo[b]thiophene gave predominantly the 3-acetyl derivative This reacted with Me2NH.HCl and H2CO (Mannich reaction) to give the corresponding keto amine, the keto group of which was reduced with NaBH4. The resulting alcs. were treated with SOCl2 to give the corresponding substituted 3-chloropropylamines. 34 references. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde

5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas:16296-68-7) belongs to benzothiophene. 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 raloxifene, zileuton, and sertaconazole, and also BTCP. Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Iddon, B.; Dickinson, R. P. published an article in 1971, the title of the article was Condensed thiophen ring systems. VI. Synthesis and reactions of 5-methyl- and 5-chloro-3-benzo[b]thienyllithium.Category: benzothiophene And the article contains the following content:

Bromination of 5-methyl- and 5-chlorobenzo[b]thiophene in CHCl3 gave 2,3-dibromo-5-methyl-, and a mixture of 20% 3-bromo-5-chloro- and 80% 2,3-dibromo-5-chlorothiophene, resp.; reaction of the 2,3-di-Br derivatives with BuLi-Et2O at 0° gave 3-bromo-5-methyl- (I) and 3-bromo-5-chlorobenzo[b]thien-2-yllithium (II). Reaction of I and II with CO2 gave the corresponding 2-carboxylic acids, and with HCl gave 5-methyl- (III) and 5-chloro-3-bromobenzo[b]thiophene (IV). Reaction of III and IV with BuLi-Et2O at -70° gave 5-methyl- (V) and 5-chlorobenzo[b]thien-3-yllithium (VI), resp. V and VI reacted with CO2, DMF, and Me2SO4 to give the corresponding 3-carboxylic acids, 3-carboxaldehydes, and 3-Me derivatives, resp. Huang-Minlon reduction of 5-methylbenzothio[b]phene-3-carboxaldehyde gave 3,5-dimethylbenzo[b]thiophene. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Category: benzothiophene

5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas:16296-68-7) belongs to benzothiophene. 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 raloxifene, zileuton, and sertaconazole, and also BTCP. Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Chapman, Norman Bellamy; Ewing, David F.; Scrowston, R. M.; Westwood, R. published an article in 1968, the title of the article was Proton magnetic resonance spectra of some benzo[b]thiophene derivatives.Formula: C9H5ClOS And the article contains the following content:

Attempts are made to correlate the chem. shifts in the 100 Mc./sec. 1H N.M.R. spectra of 42 benzo[b]thiophene derivatives with the substituents present in the mol., and the relations are rationalized where possible. Coupling constants are also recorded, and their dependence on bond order and on other factors is discussed. The changes in the chem. shifts and coupling constants when the benzo[b]thiophenes are oxidized to the 1,1-dioxides are recorded and discussed. 43 references. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Formula: C9H5ClOS

The Article related to thiophenes nmr benzo, benzothiophenes nmr, nmr benzothiophenes, nmr (nuclear magnetic resonance) and other aspects.Formula: C9H5ClOS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On March 10, 2016, Abraham, Rebecca J.; Stevens, Andrew J.; Young, Kelly A.; Russell, Cecilia; Qvist, Anastasia; Khazandi, Manouchehr; Wong, Hui San; Abraham, Sam; Ogunniyi, Abiodun D.; Page, Stephen W.; O’Handley, Ryan; McCluskey, Adam; Trott, Darren J. published an article.Formula: C9H5ClOS The title of the article was Robenidine Analogues as Gram-Positive Antibacterial Agents. And the article contained the following:

Robenidine, (2,2′-bis[(4-chlorophenyl)methylene]carbonimidic dihydrazide) (1), was active against MRSA and VRE with MIC’s of 8.1 and 4.7 μM, resp. SAR revealed tolerance for 4-Cl isosteres, and imine carbon alkylation identified a methyl/ethyl binding pocket that also accommodated a CH2OH moiety. Other analigs were active against 24 clin. MRSA and MSSA isolates, and no dose-limiting cytotoxicity at ≥2× MIC or hemolysis at ≥8× MIC was observed Polymyxin B addition engendered Escherichia coli and Pseudomonas aeruginosa Gram-neg. activity MIC’s of 4.2-21.6 μM. 1 and 75 displayed excellent microsomal stability, intrinsic clearance, and hepatic extraction ratios with T1/2 > 247 min, CLint < 7 μL/min/mg protein, and EH < 0.22 in both human and mouse liposomes for 1 and in human liposomes for I. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Formula: C9H5ClOS

The Article related to robenidine antibacterial bacterial infection, Pharmacology: Structure-Activity and other aspects.Formula: C9H5ClOS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On March 31, 2011, Pinson, Jo-Anne; Schmidt-Kittler, Oleg; Zhu, Jiuxiang; Jennings, Ian G.; Kinzler, Kenneth W.; Vogelstein, Bert; Chalmers, David K.; Thompson, Philip E. published an article.Related Products of 16296-68-7 The title of the article was Thiazolidinedione-Based PI3Kα Inhibitors: An Analysis of Biochemical and Virtual Screening Methods. And the article contained the following:

A series of synthesized and com. available compounds were assessed against PI3Kα for in vitro inhibitory activity and the results compared to binding calculated in silico. Using published crystal structures of PI3Kγ and PI3Kδ co-crystallized with inhibitors as a template, docking was able to identify the majority of potent inhibitors from a decoy set of 1000 compounds On the other hand, PI3Kα in the apo-form, modeled by induced fit docking, or built as a homol. model gave only poor results. A PI3Kα homol. model derived from a ligand-bound PI3Kδ crystal structure was developed that has a good ability to identify active compounds The docking results identified binding poses for active compounds that differ from those identified to date and can contribute to our understanding of structure-activity relationships for PI3K inhibitors. 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 structure thiazolidinedione derivative pi3k inhibitor screening preparation, Pharmacology: Structure-Activity 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 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

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