480439-45-0

Usage

Uses

Used in Organic Synthesis:
5-((Trimethylsilyl)ethynyl)-1-H-indole is used as a reagent in various organic reactions, such as palladium-catalyzed cross-coupling reactions and Sonogashira reactions, due to its ability to serve as a terminal alkyne source. Its presence in these reactions facilitates the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
5-((Trimethylsilyl)ethynyl)-1-H-indole has been studied for its potential pharmaceutical applications, particularly in the development of new drug candidates. Its unique structure and reactivity make it a promising starting material for the synthesis of bioactive compounds with potential therapeutic properties.
Used in Chemical Research:
In the field of chemical research, 5-((Trimethylsilyl)ethynyl)-1-H-indole is utilized to explore new reaction pathways, mechanisms, and the synthesis of novel organic compounds. Its versatility and utility in organic chemistry make it a valuable tool for advancing scientific knowledge and discovering new applications.

InChI:InChI=1/C9H14N2Si/c1-11-8-10-7-9(11)5-6-12(2,3)4/h7-8H,1-4H3

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 1003-21-0 5-bromo-N-methylimidazole 

Downstream Products

• 71759-92-7 5-ethynyl-1-methyl-1H-imidazole 

Relevant academic research and scientific papers

Rapid discovery of a novel series of Abl kinase inhibitors by application of an integrated microfluidic synthesis and screening platform

Drug discovery faces economic and scientific imperatives to deliver lead molecules rapidly and efficiently. Using traditional paradigms the molecular design, synthesis, and screening loops enforce a significant time delay leading to inefficient use of data in the iterative molecular design process. Here, we report the application of a flow technology platform integrating the key elements of structure-activity relationship (SAR) generation to the discovery of novel Abl kinase inhibitors. The platform utilizes flow chemistry for rapid in-line synthesis, automated purification, and analysis coupled with bioassay. The combination of activity prediction using Random-Forest regression with chemical space sampling algorithms allows the construction of an activity model that refines itself after every iteration of synthesis and biological result. Within just 21 compounds, the automated process identified a novel template and hinge binding motif with pIC50 > 8 against Abl kinase - both wild type and clinically relevant mutants. Integrated microfluidic synthesis and screening coupled with machine learning design have the potential to greatly reduce the time and cost of drug discovery within the hit-to-lead and lead optimization phases.

Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR-ABL including the T315I gatekeeper mutant

Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML.