23967-57-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-1-benzothiophene-2-carboxylic acid is used as an intermediate for the preparation of histone deacetylase inhibitors. These inhibitors play a crucial role in the development of drugs targeting various diseases, including cancer, by modulating the epigenetic regulation of gene expression. The compound's unique structure allows for the creation of potent and selective histone deacetylase inhibitors, which can potentially lead to novel therapeutic options for patients.

InChI:InChI=1/C9H5ClO2S/c10-6-2-1-3-7-5(6)4-8(13-7)9(11)12/h1-4H,(H,11,12)

Upstream product

• 35212-95-4 4-chlorobenzo[b]thiophene-2-carboxylic acid methyl ester 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 
• 65562-49-4 2,6-dichlorobenzylidenerhodanine 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 68-11-1 mercaptoacetic acid 
• 1420987-79-6 sodium 4-chlorobenzo[b]thiophen-2-carboxylate 
• 1420987-77-4 (Z)-3-(2,6-dichlorophenyl)-2-mercapto-2-propenoic acid 

Downstream Products

• 1210072-51-7 C₂₁H₁₉ClN₂O₅S 
• 1414379-09-1 1-(4-chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one 
• 1414379-27-3 1-(4-chlorobenzo[b]thiophen-2-yl)-3-(3 ,5-dichlorophenyl)-4,4,4-trifluorobut-2-en-1-one 
• 1414379-44-4 3-(4-chlorobenzo[b]thiophen-2-yl)-5-(3 ,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole 
• 846038-18-4 1-benzo[b]thiophen-4-ylpiperazine hydrochloride 
• 1420987-86-5 C₂₀H₁₈N₂S₂ 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biological pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound 8b exhibited the best activity against cancer cells. Compound 8b induced apoptosis and blocked the cell cycle. Meanwhile, 8b reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that 8b significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound 8b has a marked inhibition of STAT3-mediated Firefly luciferase activity. Molecular modeling studies revealed compound 8b occupied the pocket well with the SH2 domain in a favorable conformation.

Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry, and efficient methods for their synthesis are in high demand. This applies in particular to atropisomers derived from five-membered aromatic rings because their lower barrier for rotation among the biaryl axis limits their asymmetric synthesis. We report here an enantioselective C-H functionalization method using our chiral RhJasCp complex for the synthesis of the biaryl atropisomer types that can be accessed from three different five-membered-ring heterocycles.

Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by compound 7a at both Tyr705 and Ser727 residues. Compound 7a inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of compound 7a. Moreover, compound 7a down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, compound 7a in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that compound 7a might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy.

Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis

Schistosomiasis is a neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy relies on mass treatment with only one drug: praziquantel. Based on the 3-chlorobenzothiophene-2-hydroxamic acid J1075, a series of hydroxamic acids with different scaffolds were prepared as potential inhibitors of Schistosoma mansoni histone deacetylase 8 (SmHDAC8). The crystal structures of SmHDAC8 with four inhibitors provided insight into the binding mode and orientation of molecules in the binding pocket as well as the orientation of its flexible amino acid residues. The compounds were evaluated in screens for inhibitory activity against schistosome and human HDACs. The most promising compounds were further investigated for their activity toward the major human HDAC isotypes. The most potent inhibitors were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Two of the compounds showed significant, dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

Preparation method of 4-chloro-1-benzothiophene-2-carboxylic acid

The invention relates to the technical field of medical intermediates and particularly relates to a preparation method of 4-chloro-1-benzothiophene-2-carboxylic acid. The preparation method comprises the steps of adding water and potassium hydroxide into a reaction flask, stirring to dissolve so as to obtain a potassium hydroxide solution, dropwise adding mercaptoacetic acid at room temperature, sequentially adding 2,6-dichlorobenzaldehyde, xylene and TBAB, intensely stirring, heating to generate reflux, maintaining the reaction for 3 hours, cooling to 85 DEG C, adding water to dissolve solids, pouring the solution into a separating funnel, standing to layer, transferring a water layer into the reaction flask, dropwise adding hydrochloric acid while hot until the pH is less than 2, stirring for half an hour, filtering, rinsing filter cake with hot water, draining, transferring the filter cake into a drying oven, blowing, and drying so as to obtain 4-chloro-1-benzothiophene-2-carboxylic acid. Pressure-resistant equipment is not used, and the operation is simple and convenient, so that the preparation method is applicable to industrial production; and by taking xylene as a solvent, impurities generated in the reaction process are dissolved into xylene, are eliminated after the reaction and do not need to be removed by virtue of flammable and combustible ethyl ether, so that the potential safety hazard during the production is eliminated.

MODULATORS FOR NICOTINIC ACETYLCHOLINE RECEPTOR α2 AND α4 SUBUNITS

Positive allosteric modulators (PAMs) of nicotinic acetylcholine receptors (nAChR) are important therapeutic candidates as well as valuable research tools. We identified a novel type II PAM, (R)-7-bromo-N-(piperidin-3-yl)benzo[b]thiophene-2-carboxamide (B

Safe and Efficient Decarboxylation Process: A Practical Synthetic Route to 4-Chlorobenzo[b]thiophene

We established an improved synthetic route to 4-chlorobenzo[b]thiophene, a key intermediate in brexpiprazole synthesis, via a practical decarboxylation process in three steps. Thermal analysis demonstrated that the coexistence of the decarboxylated product with DBU should be avoided and that removal of the product outside the reactor was vital. Our process yields the target compound by distillation under reduced pressure and is safe, highly batch efficient, cost-effective, and high yielding. Furthermore, manufacturing on a pilot scale was also accomplished through our approach.

METHOD FOR PRODUCING BENZO[B]THIOPHENE COMPOUND

The present invention provides a method for producing a compound of Formula (4): wherein R1 is a hydrogen atom etc. by reacting a compound of Formula (2): wherein X1 is a leaving group, with a compound of Formula (3): wherein R1 is as defined above, in the presence of (a) a palladium compound and a tertiary phosphine or (b) a palladium carbene complex, in an inert solvent or without a solvent. The present invention can produce the compound of Formula (4), with high purity and high yield, and by a simple operation.

DIHYDROISOXAZOLE COMPOUNDS, PARASITICIDAL USES AND FORMULATIONS THEREOF

Provided are dihydroisoxazole compounds useful for controlling parasites both in animals and agriculture. Further provided are methods for controlling parasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling parasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier.

PARASITICIDAL COMPOUNDS, METHODS, AND FORMULATIONS

Provided are dihydroisoxazole compounds useful for controlling parasites both in animals and agriculture. Further provided are methods for controlling parasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling parasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. Also provided are compounds and processes useful for making the dihydroisoxazole compounds.