13771-73-8

Basic information

• Product Name: (5-fluoro-1-benzothiophen-2-yl)methanol
• Synonyms: (5-fluoro-1-benzothiophen-2-yl)methanol;(5-fluorobenzo[b]thiophen-2-yl)methanol
• CAS NO: 13771-73-8
• Molecular Formula: C₉H₇FOS
• Molecular Weight: 182.22
• Mol File: 13771-73-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 91-93°
• Appearance: /
• CAS DataBase Reference: (5-fluoro-1-benzothiophen-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (5-fluoro-1-benzothiophen-2-yl)methanol(13771-73-8)
• EPA Substance Registry System: (5-fluoro-1-benzothiophen-2-yl)methanol(13771-73-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13771-73-8(Hazardous Substances Data)

Usage

Description

(5-fluoro-1-benzothiophen-2-yl)methanol is a fluorinated benzothiophene derivative with the molecular formula C9H7FO. It features a benzene ring fused to a thiophene ring, with a fluorine atom attached to the benzene ring and a methanol group attached to the thiophene ring. This chemical compound is characterized by its unique structural features, making it a valuable building block in organic synthesis and pharmaceutical research.

Uses

Used in Organic Synthesis:
(5-fluoro-1-benzothiophen-2-yl)methanol is used as a building block in organic synthesis for the creation of various compounds. Its unique structure allows for the development of new organic molecules with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (5-fluoro-1-benzothiophen-2-yl)methanol is utilized as a key component in the synthesis of novel drugs and pharmaceuticals. Its structural features contribute to the development of innovative therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Materials Science:
(5-fluoro-1-benzothiophen-2-yl)methanol may also have potential applications in materials science, where its unique properties can be harnessed to create new materials with specific characteristics for use in various industrial processes.
Used in Industrial Processes:
(5-fluoro-1-benzothiophen-2-yl)methanol's structural features and potential applications in materials science suggest that (5-fluoro-1-benzothiophen-2-yl)methanol could be employed in other industrial processes, where its unique properties can be utilized to enhance or improve existing products and technologies.

Upstream product

• 13771-69-2 ethyl 5-fluorobenzo[b]thiophene-2-carboxylate 
• 154630-32-7 methyl 5-fluorobenzo[b]thiophene-2-carboxylate 
• 2646-90-4 2,5-difluorobenzaldehyde 

Downstream Products

• 698367-29-2 5-fluorobenzo[b]thiophene-2-carboxaldehyde 
• 698367-98-5 4-[(E)-4-(5-fluorobenzo[b]thiophen-2-yl)-2-methyl-3-buten-2-yl]-1-triphenylmethyl-1H-imidazole 

Relevant articles and documents

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.

17α-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.

Potent, orally active aldose reductase inhibitors related to zopolrestat: Surrogates for benzothiazole side chain

A broad structure-activity program was undertaken in search of effective surrogates for the key benzothiazole side chain of the potent aldose reductase inhibitor, zopolrestat (1). A structure-driven approach was pursued, which spanned exploration of three areas: (1) 5/6 fused heterocycles such as benzoxazole, benzothiophene, benzofuran, and imidazopyridine; (2) 5- membered heterocycles, including oxadiazole, oxazole, thiazole, and thiadiazole, with pendant aryl groups, and (3) thioanilide as a formal equivalent of benzothiazole. Several benzoxazole- and 1,2,4-oxadiazole- derived analogues were found to be potent inhibitors of aldose reductase from human placenta and were orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications. 3,4-Dihydro-4- oxo-3-[(5,7-difluoro-2-benzoxazolyl)methyl]-1-phthalazineacetic acid (124) was the best of the benzoxazole series (IC50 = 3.2 x 10-9 M); it suppressed accumulation of sorbitol in rat sciatic nerve by 78% at an oral dose of 10 mg/kg. Compound 139, 3,4-dihydro-4-oxo-3-[[(2-fluorophenyl)-1,2,4- oxadiazol-5-yl]methyl]-1-phthalazineacetic acid, with IC50 -8 M, caused a 69% reduction in sorbitol accumulation in rat sciatic nerve at an oral dose of 25 mg/kg. The thioanilide side chain featured in 3-[2-[[3- (trifluoromethyl)phenyl]amino]-2-thioxoethyl]-3,4-dihydro-4-oxo-1- phthalazineacetic acid (195) proved to be an effective surrogate for benzothiazole. Compound 195 was highly potent in vitro (IC50 = 5.2 x 10-8 M) but did not show oral activity when tested at 100 mg/kg. Additional structure-activity relationships encompassing a variety of heterocyclic side chains are discussed.