360576-01-8

Basic information

• Product Name: 6-BROMO-BENZO[B]THIOPHENE-2-CARBOXY LIC ACID METHYL ESTER
• Synonyms: Methyl 6-bromo-1-benzothiophene-2-carboxylate, 6-Bromo-2-(methoxycarbonyl)benzo[b]thiophene;6-BroMo-1-benzothiophene-2-carboxylic Acid Methyl Ester;6-BroMobenzothiophene-2-carboxylic Acid Methyl Ester;Methyl 6-BroMobenzo[b]thiophene-2-carboxy
• CAS NO: 360576-01-8
• Molecular Formula: C₁₀H₇BrO₂S
• Molecular Weight: 271.14
• Product Categories: Others ,Pyridazines
• Mol File: 360576-01-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 117-119°
• Boiling Point: 358.878°C at 760 mmHg
• Flash Point: 170.844°C
• Appearance: /
• Density: 1.623g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 6-BROMO-BENZO[B]THIOPHENE-2-CARBOXY LIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-BENZO[B]THIOPHENE-2-CARBOXY LIC ACID METHYL ESTER(360576-01-8)
• EPA Substance Registry System: 6-BROMO-BENZO[B]THIOPHENE-2-CARBOXY LIC ACID METHYL ESTER(360576-01-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 360576-01-8(Hazardous Substances Data)

Usage

Description

6-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is an organic compound that serves as a key intermediate in the synthesis of various benzothiophene derivatives. It is characterized by its molecular structure, which includes a benzene ring fused with a thiophene ring and a carboxylic acid group. The presence of a bromine atom at the 6-position and a methyl ester group further distinguishes its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
6-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a synthetic intermediate for the development of benzothiophene derivatives. These derivatives have potential applications as histone deacetylase inhibitors, which play a crucial role in the regulation of gene expression and are involved in various cellular processes, including cell differentiation, proliferation, and apoptosis. Inhibiting histone deacetylases can lead to the treatment of various diseases, such as cancer, neurological disorders, and cardiovascular diseases.

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

Upstream product

• 67-56-1 methanol 
• 19075-58-2 6-bromo-1-benzothiophene-2-carboxylic acid 
• 19075-61-7 6-bromobenzothiophene-3-carboxylic acid 
• 2365-48-2 Methyl thioglycolate 
• 57848-46-1 4-bromo-2-fluorobenzaldehyde 
• 74-88-4 methyl iodide 
• 17347-32-9 6-bromobenzothiophene 

Downstream Products

• 19075-58-2 6-bromo-1-benzothiophene-2-carboxylic acid 
• 17347-32-9 6-bromobenzothiophene 
• 374933-76-3 6-Brombenzothiophen-2-methanol 
• 912332-92-4 6-bromo-2-methylbenzo[b]thiophene 
• 895550-11-5 6-bromo-2-(bromomethyl)benzo[b]thiophene 
• 154650-81-4 benzo[b]thiophene-6-carbonitrile 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

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.

RHO-ASSOCIATED PROTEIN KINASE INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AS WELL AS PREPARATION METHOD AND USE THEREOF

The present invention relates to a Rho-associated protein kinase inhibitor of Formula (I), a pharmaceutical composition comprising the same, a preparation method thereof, and use thereof for the prevention or treatment of a disease mediated by the Rho-associated protein kinase (ROCK).