28856-24-8

Usage

Chemical class

Indole

Derivative of

Neurotransmitter serotonin

Function

Potent and selective serotonin reuptake inhibitor

Application

Scientific research to study serotonin receptors and physiological processes

Structure

Contains two phenyl groups attached to an indole ring and an ethylamine group

Importance

Understanding structure-activity relationships of serotonin analogs

Pharmacological properties

Promising candidate for development of new antidepressant and anxiolytic medications

InChI:InChI=1/C22H20N2/c23-16-15-20-19-13-7-8-14-21(19)24(18-11-5-2-6-12-18)22(20)17-9-3-1-4-10-17/h1-14H,15-16,23H2

Upstream product

• 591-50-4 iodobenzene 
• 29329-99-5 1,2-diphenyl-indole-3-carbaldehyde 
• 75-52-5 nitromethane 
• 18434-12-3 1,2-diphenyl-1H-indole 
• 948-65-2 2-phenyl-indole 
• 40619-61-2 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine 

Relevant academic research and scientific papers

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.

Pd(II)-Catalyzed Intramolecular C(sp2)-H Arylation of Tryptamines Using the Nonsteric NH2as a Directing Group

The free amine-directed C-H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)-H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope of the free amine-directed C-H functionalization, not limited to bulky amine substrates. Late-stage elaborations of 2-aryltryptamines achieve the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as aurantioclavine, chimonanthine, and phalarine.