244090-32-2

Basic information

• Product Name: 1-phenylindole-3-carboxylic acid methyl ester
• Synonyms: 1-phenylindole-3-carboxylic acid methyl ester
• CAS NO: 244090-32-2
• Molecular Weight: 251.285
• Mol File: 244090-32-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-phenylindole-3-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylindole-3-carboxylic acid methyl ester(244090-32-2)
• EPA Substance Registry System: 1-phenylindole-3-carboxylic acid methyl ester(244090-32-2)

Safety Data

• Hazardous Substances Data: 244090-32-2(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 942-24-5 3-methoxycarbonylindole 
• 591-50-4 iodobenzene 
• 16096-33-6 1-phenyl-1H-indole 
• 120-72-9 indole 
• 67-56-1 methanol 

Downstream Products

• 244090-34-4 1-phenyl-1H-indole-3-carboxylic acid 

Relevant articles and documents

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

Selective copper catalysed aromatic N-arylation in water

4,7-Dipyrrolidinyl-1,10-phenanthroline (DPPhen) was identified as an efficient ligand for copper catalysed selective aromatic N-arylation in water. N-Arylation of indoles, imidazoles and purines proceeds with moderate to excellent yields and complete selectivity over aliphatic amines. Aqueous medium and the possibility for low metal and ligand loadings give the process a benign environmental profile.

The copper-catalyzed N-arylation of indoles

A general method for the N-arylation of indoles using catalysts derived from Cul and trans-1,2-cyclohexanediamine (1a), trans-N,N′-dimethyl-1,2-cyclohexanediamine (2a), or N,N′-dimethyl-ethylenediamine (3) is reported. N-Arylindoles can be produced in high yield from the coupling of an aryl iodide or aryl bromide with a variety of indoles.