31529-28-9

Usage

InChI:InChI=1/C12H11NO4/c14-10(15)6-5-8-7-3-1-2-4-9(7)13-11(8)12(16)17/h1-4,13H,5-6H2,(H,14,15)(H,16,17)

Upstream product

• 3770-50-1 2-carbethoxyindole 
• 615-36-1 2-bromoaniline 
• 62-53-3 aniline 
• 3867-18-3 2-vinylaniline 
• 63158-59-8 6-ethoxy-6-oxo-5-(2-phenylhydrazono)hexanoic acid 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 111725-67-8 2-methyl-1,3-dioxo-1,2,3,4,5,10-hexahydroazepino<3,4-b>indole 
• 63158-53-2 ethyl 3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate 

Downstream Products

• 830-96-6 Indole-3-propionic acid 

Relevant academic research and scientific papers

3-(2-Carboxyethyl)indole-2-carboxylic Acid Derivatives: Structural Requirements and Properties of Potent Agonists of the Orphan G Protein-Coupled Receptor GPR17

The orphan receptor GPR17 may be a novel drug target for inflammatory diseases. 3-(2-Carboxyethyl)-4,6-dichloro-1H-indole-2-carboxylic acid (MDL29,951, 1) was previously identified as a moderately potent GPR17 agonist. In the present study, we investigated the structure-activity relationships (SARs) of 1. Substitution of the indole 1-, 5-, or 7-position was detrimental. Only small substituents were tolerated in the 4-position while the 6-position accommodated large lipophilic residues. Among the most potent compounds were 3-(2-carboxyethyl)-1H-indole-2-carboxylic acid derivatives containing the following substituents: 6-phenoxy (26, PSB-1737, EC50 270 nM), 4-fluoro-6-bromo (33, PSB-18422, EC50 27.9 nM), 4-fluoro-6-iodo (35, PSB-18484, EC50 32.1 nM), and 4-chloro-6-hexyloxy (43, PSB-1767, EC50 67.0 nM). (3-(2-Carboxyethyl)-6-hexyloxy-1H-indole-2-carboxylic acid (39, PSB-17183, EC50 115 nM) behaved as a partial agonist. Selected potent compounds tested at human P2Y receptor subtypes showed high selectivity for GPR17. Docking into a homology model of the human GPR17 and molecular dynamic simulation studies rationalized the observed SARs.

Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation

An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.

3-(2-Carboxyindol-3-yl)propionic Acid-Based Antagonists of the N-Methyl-D-aspartic Acid Receptor Associated Glycine Binding Site

A series of substituted 3-(2-carboxyindol-3-yl)propionic acids was synthesized and tested as antagonists for the strychnine-insensitive glycine binding site of the NMDA receptor.Chlorine, and other small electron-withdrawing substituents in the 4- and 6-p

Novel Indole-2-carboxylates as Ligands for the Strychnine-Insensitive N-Methyl-D-aspartate-Linked Glycine Receptor

A series of indole-2-carboxylates were prepared and evaluated for their ability to inhibit the binding at the strychnine-insensitive glycine receptor that is associated with the NMDA-PCP-glycine receptor complex.All of the compounds were selective for the glycine site relative to other sites on the receptor macrocomplex and several of the compounds in this series were found to have submicromolar affinity for this receptor.The lead compound, 2-carboxy-6-chloro-3-indoleacetic acid (Ki = 1.6 μM vsglycine), was also found to noncompetitively inhibit the binding of MK-801, a ligand for the phencyclidine site on the receptor macrocomplex.These latter data suggest that the compound functions as an antagonist at the strychnine-insensitive glycine receptor.The structural activity relationships within this series of indole-2-carboxylates is discussed and several key pharmacophores are identified for this series of glycine ligands.In general, the most potent compounds were the C-3 acetamides, with N-propyl-2-carboxy-6-chloro-3-indoleacetamide having the highest receptor affinity.

Excitatory amino acid antagonists

The present invention is directed to the discovery of a new use for a group of known 2-carboxylic indole derivatives. The compounds are excitatory amino acid antagonists.

Syntheses a partir de la cyano-2 cyclopentanone: application des arylhydrazones de l'acide cyano-5 oxo-5 pentanoique a la preparation de derives indoliques

Fischer's cyclisation of 5-cyano 5-oxo pentanoic acid arylhydrazones affords either 3-(2-carboxy 1H-3-indolyl) propanoic acids and derivatives thereof, azepinoindoles or an acetyl diazepinone according to the nature of the cyclising reagent.

α-DIMETHYLAMINOMETHYLENE DERIVATIVES OF SUCCINIMIDE AND GLUTARIMIDE IN THE FISHER REACTION

A study has been made of the behavior of α-dimethylaminomethylene derivatives of succinic and glutaric acid N-methylimides when reacted with different arylhydrazines under the conditions of the Fisher reaction.