31529-27-8

Basic information

• Product Name: 3-(Carboxymethyl)-1H-indole-2-carboxylic acid
• Synonyms: 3-(Carboxymethyl)-1H-indole-2-carboxylic acid
• CAS NO: 31529-27-8
• Molecular Formula: C₁₁H₉NO₄
• Molecular Weight: 219.19346
• Mol File: 31529-27-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 235-236 °C
• Boiling Point: 537.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.545±0.06 g/cm3(Predicted)
• PKA: 3.54±0.30(Predicted)
• CAS DataBase Reference: 3-(Carboxymethyl)-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Carboxymethyl)-1H-indole-2-carboxylic acid(31529-27-8)
• EPA Substance Registry System: 3-(Carboxymethyl)-1H-indole-2-carboxylic acid(31529-27-8)

Safety Data

• Hazardous Substances Data: 31529-27-8(Hazardous Substances Data)

Upstream product

• 63158-60-1 3-ethoxycarbonylmethyl-1H-indole-2-carboxylic acid ethyl ester 
• 17278-46-5 2-Oxoglutaric acid phenylhydrazone 
• 156362-00-4 methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate 
• 328-50-7 α-ketoglutaric acid 
• 119224-54-3 2-(2-Ethoxycarbonyl-3-indolyl)-2-oxoessigsaeureethylester 
• 256931-83-6 (2-ethoxycarbonylindol-3-yl)ethyl-2-hydroxyacetate 
• 1501-06-0 diethyl 2-acetylglutarate 
• 70794-20-6 2-(Phenyl-hydrazono)-pentanedioic acid diethyl ester 
• 100374-00-3 4-cyano-2-((E)-phenylhydrazono)-butyric acid ethyl ester 
• 100-63-0 phenylhydrazine 

Downstream Products

• 73031-14-8 2-(1H-indol-3-yl)-N-benzyl acetamide 
• 101731-73-1 3-(benzylcarbamoyl-methyl)-indole-2-carboxylic acid 
• 83-34-1 3-Methylindole 
• 87-51-4 indole-3-acetic acid 
• 74693-46-2 3-Carboxymethyl-1-(2,4-dinitro-benzoyl)-1H-indole-2-carboxylic acid 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 778-82-5 ethyl 3-indoleacetate 
• 109693-85-8 [3-(2-benzylamino-ethyl)-indol-2-yl]-methanol 
• 60441-99-8 2-benzyl-4,9-dihydro-β-carboline-1,3-dione 
• 109653-39-6 N-benzyl-N-(1-oxo-1,9-dihydro-pyrano[3,4-b]indol-3-yl)-acetamide 
• 102316-90-5 3-(benzylcarbamoyl-methyl)-indole-2-carboxylic acid ethyl ester 

Relevant articles and documents

The Chemistry of Ethyl 3-(2-Ethoxy-2-oxoethyl)-1 H -indole-2-carboxylate: Synthesis of Pyrimido[4,5- b ]indoles and Diethyl 4-Hydroxyquinoline-2,3-dicarboxylate via Intramolecular Cyclizations

We report the synthesis of a new series of 2-oxo-1,2,4,9-tetrahydro-3H-pyrimido[4,5-b]indole derivatives and diethyl 4-hydroxyquinoline-2,3-dicarboxylate starting from ethyl 3-(2-ethoxy-2-oxoethyl)-1H-indole-2-carboxylate. Intramolecular cyclization forme

Regiospecific functionalization of indole-2-carboxylates and diastereoselective preparation of the corresponding indolines

The N-acyl derivatives of 3-substituted indole-2-carboxylates prepared through several routes were submitted to catalytic hydrogenation affording either cis- or trans-indoline diastereomers after quantitative C-2 epimerization.

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.