698367-29-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-1-benzothiophene-2-carbaldehyde is used as a building block for the preparation of various pharmaceuticals. Its unique structure allows it to be a key component in the synthesis of drugs with potential therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Fluoro-1-benzothiophene-2-carbaldehyde serves as a starting material for the synthesis of compounds with potential applications in pest control and crop protection, contributing to the development of effective and environmentally friendly products.
Used in Materials Science:
5-Fluoro-1-benzothiophene-2-carbaldehyde has been studied for its potential applications in materials science. Its incorporation into materials can lead to the development of new properties, such as improved stability or specific interactions with other molecules.
Used as a Chemical Intermediate:
5-Fluoro-1-benzothiophene-2-carbaldehyde is also used as a chemical intermediate in the production of specialty chemicals. Its versatility in organic synthesis makes it a valuable component in the creation of a wide range of chemical products.
Overall, 5-Fluoro-1-benzothiophene-2-carbaldehyde is a versatile chemical compound with applications spanning across various industries, including pharmaceuticals, agrochemicals, materials science, and as a chemical intermediate for specialty chemicals. Its unique structure and properties make it a valuable asset in the development of new and innovative products.

Upstream product

• 70060-12-7 5-fluorobenzo[b]thiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 70060-13-8 5-fluorobenzo[b]thiophene-2-carboxylic acid 
• 13771-69-2 ethyl 5-fluorobenzo[b]thiophene-2-carboxylate 
• 2646-90-4 2,5-difluorobenzaldehyde 
• 13771-73-8 (5-fluorobenzo[b]thiophen-2-yl)methanol 
• 154630-32-7 methyl 5-fluorobenzo[b]thiophene-2-carboxylate 

Relevant academic research and scientific papers

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.

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.

C17,20-lyase inhibitors I. Structure-based de novo design and SAR study of C17,20-lyase inhibitors.

Novel nonsteroidal C(17,20)-lyase inhibitors were synthesized using de novo design based on its substrate, 17 alpha-hydroxypregnenolone, and several compounds exhibited potent C(17,20)-lyase inhibition. However, in vivo activities were found to be short-lasting, and in order to improve the duration of action, a series of benzothiophene derivatives were evaluated. As a result, compounds 9h, (S)-9i, and 9k with nanomolar enzyme inhibition (IC(50)=4-9 nM) and 9e (IC(50)=27 nM) were identified to have powerful in vivo efficacy with extended duration of action. The key structural determinants for the in vivo efficacy were demonstrated to be the 5-fluoro group on the benzothiophene ring and the 4-imidazolyl moiety. Superimposition of 9k and 17 alpha-hydroxypregnenolone demonstrated their structural similarity and enabled rationalization of the pharmacological results. In addition, selected compounds were also identified to be potent inhibitors of human enzyme with IC(50) values of 20-30 nM.