40619-61-2

Basic information

• Product Name: 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine
• Synonyms: 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine
• CAS NO: 40619-61-2
• Molecular Weight: 236.316
• Mol File: 40619-61-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine(40619-61-2)
• EPA Substance Registry System: 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine(40619-61-2)

Safety Data

• Hazardous Substances Data: 40619-61-2(Hazardous Substances Data)

Upstream product

• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 530-50-7 1,1-Diphenylhydrazine 
• 61-54-1 tryptamine 
• 591-50-4 iodobenzene 
• 61798-24-1 (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane 
• 63050-02-2 3-(2-nitrovinyl)-1-phenyl-1H-indole 
• 32542-59-9 1-phenyl-1H-indol-3-carboxaldehyde 

Downstream Products

• 28856-24-8 2-(1,2-diphenyl-1H-indol-3-yl)ethanamine 

Relevant articles and documents

Synthesis of DPIE [2-(1,2-Diphenyl-1H-indol-3-yl)ethanamine] Derivatives and Their Regulatory Effects on Pro-Inflammatory Cytokine Production in IL-1β-Stimulated Primary Human Oral Cells

Interleukin-1 beta (IL-1β) has diverse physiological functions and plays important roles in health and disease. In this report, we focus on its function in the production of pro-inflammatory cytokines, including IL-6 and IL-8, which are implicated in several autoimmune diseases and host defense against infection. IL-1β activity is markedly dependent on the binding affinity toward IL-1 receptors (IL-1Rs). Several studies have been conducted to identify suitable small molecules that can modulate the interactions between 1L-1β and 1L-1R1. Based on our previous report, where DPIE [2-(1,2-Diphenyl-1H-indol-3-yl)ethanamine] exhibited such modulatory activity, three types of DPIE derivatives were synthesized by introducing various substituents at the 1, 2, and 3 positions of the indole group in DPIE. To predict a possible binding pose in complex with IL-1R1, a docking simulation was performed. The effect of the chemicals was determined in human gingival fibroblasts (GFs) following IL-1β induction. The DPIE derivatives affected different aspects of cytokine production. Further, a group of the derivatives enabled synergistic pro-inflammatory cytokine production, while another group caused diminished cytokine production compared to DPIE stimulation. Some groups displayed no significant difference after stimulation. These findings indicate that the modification of the indole site could modulate IL-1β:IL1R1 binding affinity to reduce or enhance pro-inflammatory cytokine production.

A Highly Regio- and Diastereoselective Four-Component Reaction to Construct Polycyclic Bispiroindolines from 2-Isocyanoethylindoles and Isocyanates

A one-pot multicomponent domino reaction between 2-isocyanoethylindoles and isocyanates for the diastereoselective construction of polycyclic bispiroindolines was developed. Fused polycyclic bispiroindolines containing two contiguous spiral atoms were afforded in moderate to good yields with excellent regio- and diastereoselectivities through a four-component Ugi-type reaction (U-4CR) under mild conditions.

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.