550998-53-3

Basic information

• Product Name: METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE
• Synonyms: METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE
• CAS NO: 550998-53-3
• Molecular Formula: C₁₀H₇BrO₂S
• Molecular Weight: 271.13038
• Mol File: 550998-53-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 99-102°C
• Boiling Point: 358.9°C at 760 mmHg
• Flash Point: 170.8°C
• Appearance: /
• Density: 1.622g/cm³
• Vapor Pressure: 2.47E-05mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(550998-53-3)
• EPA Substance Registry System: METHYL 7-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(550998-53-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 550998-53-3(Hazardous Substances Data)

Usage

General Description

Methyl 7-bromo-1-benzothiophene-2-carboxylate is a chemical compound with a molecular formula C12H9BrO2S. It is a derivative of benzothiophene, which is a heterocyclic compound containing both benzene and thiophene rings. This chemical is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It can also be used as a building block in the preparation of other organic compounds. Methyl 7-bromo-1-benzothiophene-2-carboxylate is a versatile and valuable compound in organic synthesis due to its reactivity and potential applications in the development of new drugs and agricultural products.

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

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

Downstream Products

• 19075-59-3 7-bromo-1-benzothiophene-2-carboxylic acid 
• 1505-61-9 7-methylbenzo[b]thiophene-2-carboxylic acid 
• 1423-61-6 7-bromobenzo(b)thiophene 

Relevant articles and documents

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.

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.

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.