155134-26-2

Basic information

• Product Name: 1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-, methyl ester
• CAS NO: 155134-26-2
• Molecular Formula: C17H15NO2
• Molecular Weight: 265.312
• Mol File: 155134-26-2.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-, methyl ester(155134-26-2)
• EPA Substance Registry System: 1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-, methyl ester(155134-26-2)

Safety Data

• Hazardous Substances Data: 155134-26-2(Hazardous Substances Data)

Usage

Molecular class

Indole derivatives

Structural features

Indole ring with a carboxylic acid group, phenylmethyl side chain, and methyl ester functional group

Common uses

Building block for the synthesis of various drugs and biologically active molecules in the pharmaceutical industry

Potential pharmacological activities

Possesses the potential to exhibit various pharmacological activities due to its structural features

Value in synthesis

Valuable intermediate in the fine chemical synthesis

Use in research and development

Used as a starting material in the design and synthesis of new chemical entities.

Upstream product

• 624-75-9 iodoacetonitrile 
• 78688-62-7 (E)-3-Phenylamino-pent-2-enedioic acid dimethyl ester 
• 942-24-5 3-methoxycarbonylindole 
• 100-39-0 benzyl bromide 
• 122394-37-0 methyl α-formyl(o-bromophenyl)acetate 
• 100-46-9 benzylamine 
• 620-05-3 iodomethylbenzene 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 324738-51-4 2′-N-benzylaminophenylacetylene 
• 1265902-10-0 methyl 3-(benzylamino)-2-(2-bromophenyl)acrylate 
• 771-50-6 1H-indole-3-carboxylic acid 
• 3376-40-7 N-benzyl-N-phenylhydroxylamine 

Downstream Products

• 27018-76-4 1-benzylindole-3-carboxylic acid 
• 1392495-71-4 C₅₂H₄₄N₁₀O₂S₂ 
• 1392495-72-5 C₅₀H₄₀N₁₀O₂S₂ 
• 1392495-73-6 C₅₀H₃₈Br₂N₁₀S₂ 
• 1392495-74-7 C₅₀H₃₈N₁₂O₄S₂ 
• 1392495-75-8 C₅₀H₃₈Br₂N₁₀S₂ 
• 1392495-76-9 C₅₀H₃₈Br₂N₁₀S₂ 
• 1392495-77-0 C₄₆H₃₆N₁₀O₂S₂ 
• 56559-63-8 1-benzyl-1H-indole-3-carbohydrazide 
• 770732-47-3 C₁₇H₁₅N₅S 
• 1392495-67-8 C₃₆H₃₂N₁₀S₂ 
• 1392495-68-9 C₅₀H₄₀N₁₀S₂ 
• 1392495-69-0 C₅₀H₃₈F₂N₁₀S₂ 
• 1392495-70-3 C₅₀H₄₀N₁₀O₂S₂ 

Relevant articles and documents

Ferric chloride-catalyzed synthesis of indoles using the intramolecular amination of aryl bromides

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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.

Synthesis of indoles via electron-catalyzed intramolecular C?N bond formation

A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C?N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number o