1073354-51-4

Basic information

• Product Name: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester
• Synonyms: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester;1H-Indole, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS NO: 1073354-51-4
• Molecular Formula: C₂₁H₂₄BNO₄S
• Molecular Weight: 397.3
• Mol File: 1073354-51-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester(1073354-51-4)
• EPA Substance Registry System: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester(1073354-51-4)

Safety Data

• Hazardous Substances Data: 1073354-51-4(Hazardous Substances Data)

Usage

General Description

N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester is a chemical compound, often used in advanced organic synthesis, which features both a tosyl (toluenesulfonyl) moiety and a boronic ester group. The tosyl group enhances the compound's reactivity, making it ideal as a substrate for various chemical reactions. Additionally, the boronic ester component can engage in Suzuki coupling reactions, a popular method for forming carbon-carbon bonds in organic synthesis. The inclusion of the indole core offers further opportunities for creating complex chemical structures, given the ubiquitous presence of this motif in bioactive molecules and natural products. Hence, N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester serves as a versatile building block in the field of chemical synthesis.

Upstream product

• 26340-47-6 3-Iodo-1H-indole 
• 120-72-9 indole 
• 170456-80-1 3-iodo-1-tosyl-1-indole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 98-59-9 p-toluenesulfonyl chloride 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 13637-37-1 1H,1'H-[3,3']biindolyl 
• 763138-83-6 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl 
• 36797-43-0 3-methyl-N-(p-toluenesulfonyl)indole 
• 1338575-78-2 tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate 

Relevant articles and documents

Nature-Inspired (di)Azine-Bridged Bisindole Alkaloids with Potent Antibacterial in Vitro and in Vivo Efficacy against Methicillin-Resistant Staphylococcus aureus

Natural bisindole alkaloids such as Hyrtinadine A and Alocasin A, which are known to exhibit diverse bioactivities, provide promising chemical scaffolds for drug development. By optimizing the Masuda borylation-Suzuki coupling sequence, a library of various natural product-derived and non-natural (di)azine-bridged bisindoles was created. While unsubstituted bisindoles were devoid of antibacterial activity, 5,5′-chloro derivatives were highly active against methicillin-resistant Staphylococcus aureus (MRSA) and further Gram-positive pathogens at minimal inhibitory concentrations ranging from 0.20 to 0.78 μM. These compounds showed strong bactericidal killing effects but only moderate cytotoxicity against human cell lines. Furthermore, the two front-runner compounds 4j and 4n exhibited potent in vivo efficacy against MRSA in a mouse wound infection model. Although structurally related bisindoles were reported to specifically target pyruvate kinase in MRSA, antibacterial activity of 4j and 4n is independent of pyruvate kinase. Rather, these compounds lead to bacterial membrane permeabilization and cellular efflux of low-molecular-weight molecules.

Pyrimidine derivatives Anaplastic lymphoma kinase inhibitors

The invention belongs to the field of a medical technology and specifically relates to a pyrimidine derivative type anaplastic lymphoma kinase inhibitor as shown in the general formula (I) or its stereisomer, or its pharmaceutically acceptable salt, ester or solvate, wherein R1, R2, R3, R4, R5 and A ring are as defined in the specification. The invention also relates to a preparation method of the compounds, a pharmaceutic preparation and a pharmaceutical composition containing the compounds and an application of the compound or its stereisomer, or its pharmaceutically acceptable salt, ester or solvate in the preparation of medicines for treating and/or preventing diseases related to anaplastic lymphoma kinase-mediated cancer.