81524-74-5

Basic information

• Product Name: 5-azidoindole
• Synonyms: 5-azidoindole;5-azido-1H-indole
• CAS NO: 81524-74-5
• Molecular Formula: C₈H₆N₄
• Molecular Weight: 158.16
• Mol File: 81524-74-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 5-azidoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-azidoindole(81524-74-5)
• EPA Substance Registry System: 5-azidoindole(81524-74-5)

Safety Data

• Hazardous Substances Data: 81524-74-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6N4/c9-12-11-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

Upstream product

• 5192-03-0 5-amino-1H-indole 
• 16066-91-4 5-iodo-1H-indole 
• 6146-52-7 5-nitroindole 
• 10075-50-0 5-bromo-1H-indole 
• 144104-59-6 1H-indole-5-boronic acid 

Downstream Products

• 1397395-29-7 1-(indol-5-yl)-4-cyclohexyl-1H-1,2,3-triazole 
• 1421345-22-3 C₂₁H₁₇N₅O₃ 
• 1421345-23-4 C₂₁H₁₇N₅O₃ 
• 1608463-99-5 (S)-1-(1-(1H-indol-5-yl)-1H-1,2,3-triazol-4-yl)-3-(2-((S)-3-(biphenyl-4-yl)-2-hydroxypropoxy)ethoxy)propan-2-ol 
• 1266605-81-5 C₂₅H₂₇F₂N₉O 

Relevant articles and documents

ISOINDOLINE COMPOUND, AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION, AND APPLICATION OF ISOINDOLINE COMPOUND

The present invention relates to an isoindoline compound as represented by general formula (I) and used as a CRBN regulator, and a preparation method, a pharmaceutical composition, and an application of the isoindoline compound. Specifically, a class of polysubstituted isoindoline compound provided in the present invention, as a class of CRL4CRBN E3 ubiquitin ligase regulator having a novel structure, has good anti-tumor activity and immunoregulatory activity, and can be used for preparing drugs for treating diseases associated with a CRL4CRBN E3 ubiquitin ligase.

Synthesis and antimicrobial activity of 4-substituted 1,2,3-triazole-coumarin derivatives

A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 μg/mL). Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes.

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

The dopamine D3 receptor (D3R) is a target of pharmacotherapeutic interest in a variety of neurological disorders including schizophrenia, Parkinson's disease, restless leg syndrome, and drug addiction. A common molecular template used in the development of D3R-selective antagonists and partial agonists incorporates a butylamide linker between two pharmacophores, a phenylpiperazine moiety and an extended aryl ring system. The series of compounds described herein incorporates a change to that chemical template, replacing the amide functional group in the linker chain with a 1,2,3-triazole group. Although the amide linker in the 4-phenylpiperazine class of D3R ligands has been previously deemed critical for high D3R affinity and selectivity, the 1,2,3-triazole moiety serves as a suitable bioisosteric replacement and maintains desired D3R-binding functionality of the compounds. Additionally, using mouse liver microsomes to evaluate CYP450-mediated phase I metabolism, we determined that novel 1,2,3-triazole-containing compounds modestly improves metabolic stability compared to amide-containing analogues. The 1,2,3-triazole moiety allows for the modular attachment of chemical subunit libraries using copper-catalyzed azide-alkyne cycloaddition click chemistry, increasing the range of chemical entities that can be designed, synthesized, and developed toward D3R-selective therapeutic agents.