6314-43-8

Usage

Uses

Used in Pharmaceutical Research and Organic Synthesis:
Benzo[b]thiophene-2-methanamine is utilized as a key intermediate in the synthesis of heterocyclic compounds for medicinal purposes. Its unique structure and reactivity make it a valuable component in the development of new drugs and pharmaceutical agents.
Used in Drug Discovery and Development:
Benzo[b]thiophene-2-methanamine serves as a building block in the creation of novel therapeutic agents, contributing to the advancement of drug discovery and development. Its potential applications in this field are vast, as heterocyclic compounds are often found in biologically active molecules.
Used in the Production of Dyes, Pigments, and Polymers:
Beyond its pharmaceutical applications, Benzo[b]thiophene-2-methanamine may also find use in various industrial applications, such as in the manufacturing of dyes, pigments, and polymers, where its unique chemical properties can be harnessed to create new materials with specific characteristics.

InChI:InChI=1/C9H9NS/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-5H,6,10H2

Upstream product

• 6314-42-7 benzo[b]thiophene-2-carboxamide 
• 39827-11-7 benzothiophene-2-carboxylic acid chloride 
• 6314-28-9 benzo[b]thiophene-2-carboxylic acid 
• 276692-18-3 benzo[b]thiophene-2-carbaldehyde oxime 
• 95-15-8 Benzo[b]thiophene 

Downstream Products

• 911055-95-3 2-adamantan-1-yl-N-benzo[b]thiophen-2-ylmethyl-acetamide 
• 1018480-40-4 C₂₀H₁₅F₃N₄O₂S₂ 
• 1018480-41-5 C₂₁H₁₆F₃N₃O₂S₂ 
• 1041850-54-7 benzo[b]thiophen-2-ylmethyl-{4-[4-(4-fluorophenyl)-2-methylsulfanyl-1H-imidazol-5-yl]pyridin-2-yl}amine 
• 1105691-08-4 N-(benzo[b]thiophen-2-ylmethyl)-2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide 
• 1422360-64-2 C₂₀H₁₈N₄O₂S 

Relevant academic research and scientific papers

Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus

Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.

Convenient one-pot methodology for the primary aminomethylation of electron rich heterocycles

Primary aminomethyl groups were introduced into the 2-position of electron rich heterocycles in moderate to good yields by a one-pot sequence involving lithiation, transmetalation into an organozinc reagent and treatment with 1-(triphenylphosphoroylideneaminomethyl)benzotriazole (betmip).