154630-32-7

Basic information

• Product Name: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: METHYL 5-FLUORO-1-BENZOTHIOPHENE-2-CARBOXYLATE;5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;5-Fluoro-2-(methoxycarbonyl)benzo[b]thiophene;Ethyl 5-fluorobenzo[b]thiophene-2-carboxylate, 96%
• CAS NO: 154630-32-7
• Molecular Formula: C₁₀H₇FO₂S
• Molecular Weight: 210.22
• Mol File: 154630-32-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 80-82°C
• Boiling Point: 308.344 °C at 760 mmHg
• Flash Point: 140.281 °C
• Appearance: /
• Density: 1.355 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(154630-32-7)
• EPA Substance Registry System: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(154630-32-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 154630-32-7(Hazardous Substances Data)

Usage

General Description

5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is a chemical compound with the molecular formula C10H7FO2S. It is a methyl ester derivative of 5-fluorobenzo[b]thiophene-2-carboxylic acid, which is a substituted thiophene with a carboxylic acid group. This chemical compound is commonly used in research and pharmaceutical applications, particularly in the development of new drugs and medications. Its unique structure and properties make it a valuable building block in organic synthesis, and it has potential medicinal properties that make it of interest to scientists and researchers in the field of pharmacology.

InChI:InChI=1/C10H7FO2S/c1-13-10(12)9-5-6-4-7(11)2-3-8(6)14-9/h2-5H,1H3

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1191415-34-5 2-(2,2-dibromovinyl)-4-fluorobenzenethiol 
• 70060-12-7 5-fluorobenzo[b]thiophene 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 2646-90-4 2,5-difluorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 

Downstream Products

• 13771-73-8 (5-fluorobenzo[b]thiophen-2-yl)methanol 
• 70060-12-7 5-fluorobenzo[b]thiophene 
• 70060-13-8 5-fluorobenzo[b]thiophene-2-carboxylic acid 
• 698367-29-2 5-fluorobenzo[b]thiophene-2-carboxaldehyde 

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.

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 μM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 μM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 ± 0.37 μM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.

17a-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.