35212-95-4

Basic information

• Product Name: 4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 4-chloro-2-benzothiophenecarboxylic acid methyl ester;4-chlorobenzothiophene-2-carboxylic acid methyl ester;methyl 4-chlorobenzothiophene-2-carboxylate
• CAS NO: 35212-95-4
• Molecular Formula: C₁₀H₇ClO₂S
• Molecular Weight: 226.68
• Mol File: 35212-95-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 95-97°
• Boiling Point: 338.693°C at 760 mmHg
• Flash Point: 158.636°C
• Appearance: /
• Density: 1.392g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(35212-95-4)
• EPA Substance Registry System: 4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(35212-95-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 35212-95-4(Hazardous Substances Data)

Usage

Description

4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER, also known as Methyl 4-Chlorobenzo[b]thiophene-2-carboxylate, is an organic compound with the molecular formula C10H7ClO2S. It is characterized by its unique chemical structure, which features a benzene ring fused to a thiophene ring, with a chlorine atom, a carboxylic acid group, and a methyl ester group attached. 4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is known for its potential applications in the pharmaceutical industry due to its chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a reactant for the synthesis of novel tachykinin NK2 receptor antagonists. These antagonists are important in the development of medications targeting various conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and inflammatory bowel disease (IBD). 4-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER's unique structure allows it to interact with the tachykinin NK2 receptor, potentially leading to the development of new therapeutic agents for these conditions.

InChI:InChI=1/C10H7ClO2S/c1-13-10(12)9-5-6-7(11)3-2-4-8(6)14-9/h2-5H,1H3

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 

Downstream Products

• 23967-57-9 4-chloro-2-benzo[b]thiophenecarboxylic acid 
• 1414379-44-4 3-(4-chlorobenzo[b]thiophen-2-yl)-5-(3 ,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole 
• 1414379-27-3 1-(4-chlorobenzo[b]thiophen-2-yl)-3-(3 ,5-dichlorophenyl)-4,4,4-trifluorobut-2-en-1-one 
• 1414379-09-1 1-(4-chlorobenzo[b]thiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one 

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.

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.

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