550998-53-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs, enhancing the range of therapeutic options available.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE is utilized as an intermediate in the production of agrochemicals, playing a role in the synthesis of compounds that can improve crop protection and yield.
Used in Organic Synthesis:
METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE is used as a building block in the preparation of other organic compounds, showcasing its reactivity and importance in creating a diverse array of chemical entities for various applications.

InChI:InChI=1/C10H7BrO2S/c1-13-10(12)8-5-6-3-2-4-7(11)9(6)14-8/h2-5H,1H3

Upstream product

• 1072-85-1 o-fluorobromobenzene 
• 149947-15-9 3-bromo-2-fluorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 

Downstream Products

• 19075-59-3 7-bromo-1-benzothiophene-2-carboxylic acid 

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.

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.

Antagonizing STAT3 activation with benzo[b]thiophene 1, 1-dioxide based small molecules

STAT3 is an attractive therapeutic target for cancer therapy. However, due to low potency or poor druggability, none of its inhibitors are clinically available. Herein, a series of aminobenzo[b]thiophene 1, 1-dioxides with good drug-likeness properties were designed, synthesized and evaluated as STAT3 inhibitors. Most of them exhibited higher antitumor activity than the small-molecule STAT3 inhibitor, Stattic. Compound 15 was the most potent and had an IC50range in 0.33–0.75?μM in various cancer cell lines. The overexpressed and IL-6 induced phosphorylation levels of STAT3 were both inhibited by 15 without influencing the phosphorylation levels of the upstream kinases Src and Jak2. 15 also suppressed the expressions of STAT3 downstream gene, Bcl-2. 15 effectively increased the ROS levels of cancer cells, induced cancer cell apoptosis and abolished the colony formation ability of cancer cells without affecting bypass kinase p-Erk. Furthermore, 15 in?vivo induced significant antitumor responses, and exhibited less toxicity than Doxorubicin. Together, this study described a class of new STAT3 inhibitors as antitumor agents.

N-(piperidin-4-yl)benzo[b]thiophenecarboxamide derivatives, preparation method therof, and pharmaceutical composition for use in preventing or treating Urotensin-Ⅱ receptor activity related diseases containing the same as an active ingredient

The present invention relates to N-(piperidin-4-yl)benzo[b]thiophenecarboxamide derivatives, a manufacturing method thereof, and a pharmaceutical composition for preventing or treating urotensin-II receptor activity-related diseases comprising the same as an active ingredient. The N-(piperidin-4-yl)benzo[b]thiophenecarboxamide derivatives can be usefully used for preventing or treating urotensin-II receptor activity-related diseases such as congestive heart failure, ischemic heart, myocardial infarction, cardiomegaly, fibrosis cordis, coronary artery disease, arteriosclerosis, hypertension, asthma, renal failure, diabetes, vasculitis, neurodegenerative disease, stroke, pain, depressive disorder, psychosis, cancer, etc., by acting as an antagonist with respect to a urotensin-II receptor.COPYRIGHT KIPO 2016

BENZOTHIOPHENE UREA, BENZOFURANE UREA, AND INDOLE UREA, AND USE OF THE SAME AS ALPHA-7 ACHR AGONISTS

The invention relates to novel benzothiophene urea, benzofurane urea, and indole urea, and to the use thereof for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration power, learning capacity and/or memory retention.

2-HETEROARYL CARBOXAMIDES

The invention relates to the novel 2-heteroaryl carboxamides according to formula (I), wherein R1 represents 1-aza-bicyclo [2.2.2]oct-3-yl, which is optionally replaced via the nitrogen atom by a group selected from the family C1-C4 alkyl, benzyl and oxy, A represents oxygen or sulfur, the ring B represents benzo or pyrido that are optionally replaced by the groups from the family of halogen, cyano, formyl, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6 alkyl and C1-C6 alkoxy, E represents C=C, aryl and heteroaryl, wherein aryl and heteroaryl may be replaced by groups from the family of halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6 alkoxy and C1-C6 alkyl, and to the solvents, salts or solvents of salts of said compounds. The invention also relates to the use of said compounds in the production of drugs for the treatment and/or the prophylaxis of diseases and for improving perception, power of concentration, learning power and/or retentiveness of memory.