120716-95-2

Usage

Uses

Used in Research Applications:
(2-carboxy-5-chloro-indol-3-yl)-acetic acid is used as a research chemical to study the effects of auxin on plant growth and development. Its unique structure with a carboxylic acid group and a chlorine atom allows researchers to explore how these modifications affect the compound's interaction with plant systems and its overall biological activity.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2-carboxy-5-chloro-indol-3-yl)-acetic acid is used as a potential therapeutic agent. Its exploration is driven by the understanding of auxin's role in plant growth and the possibility that similar mechanisms could have applications in medicine. (2-carboxy-5-chloro-indol-3-yl)-acetic acid is being studied for its potential to influence cellular processes and contribute to the development of new treatments for various conditions.
Used in Agrochemical Formulations:
(2-carboxy-5-chloro-indol-3-yl)-acetic acid may also find use in the agrochemical industry as a component of formulations designed to enhance plant growth and productivity. Its role as an auxin derivative suggests that it could be utilized to improve crop yields and quality by modulating plant development processes.

Upstream product

• 72963-97-4 (2-ethoxycarbonyl-5-chloro-indol-3-yl)-acetic acid ethyl ester 
• 106-47-8 4-chloro-aniline 
• 1501-06-0 diethyl 2-acetylglutarate 

Downstream Products

• 221188-41-6 [5-chloro-1-(4-fluoro-benzyl)-1H-indol-3-yl]-acetic acid ethyl ester 
• 1912-45-4 2-(5-chloro-1H-indol-3-yl)acetic acid 

Relevant academic research and scientific papers

New N-(pyridin-4-yl)-(indol-3-yl)acetamides and propanamides as antiallergic agents

A series of new N-(pyridin-4-yl)-(indol-3-yl)alkylamides 44-84 has been prepared in the search of novel antiallergic compounds. Synthesis of the desired ethyl (2-methyindol-3-yl)acetates 1-4 was achieved by indolization under Fischer conditions; Japp-Klingemann method followed by 2- decarboxylation afforded the ethyl (indol-3-yl)alkanoates 17-25. Amidification was successfully carried out by condensation of the corresponding acids or their N-aryl(methyl) derivatives with 4-aminopyridine promoted by 2-chloro-1-methylpyridinium iodide. Efforts to improve the antiallergic potency of the title series by variation of the indole substituents (R1, R2, R) and the length of the alkanoic chain (n = 1, 2, 3) led to the selection of N-(pyridin-4-yl)-[1-(4-fluorobenzyl)indol-3- yl]acetamide 45, out of 41 compounds. This amide was 406-fold more potent than astemizole in the ovalbumin-induced histamine release assay, using guinea pig peritoneal mast cells, with an IC50 = 0.016 μM. Its inhibitory activity in IL-4 production test from Th-2 cells was identical to that of the reference histamine antagonist (IC50 = 8.0 μM) and twice higher in IL-5 assay: IC50 = 1.5 and 3.3 μM, respectively. In vivo antiallergic activity evaluation confirmed efficiency of 45 in sensitized guinea pig late phase eosinophilia inhibition, after parenteral and oral administration at 5 and 30 mg/kg, respectively. Its efficiency in inhibition of microvascular permeability was assessed in two rhinitis models; ovalbumin and capsaicin- induced rhinorrhea could be prevented after topical application of submicromolar concentrations of 45 (IC50 = 0.25 and 0.30 μM); and it also exerted significant inhibitory effect in the first test after iv and oral administration, with ID50 = 0.005 and 0.46 mg/kg.

Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders

Compositions containing certain indole-2-carboxylate compounds and derivatives are described as being therapeutically effective in treatment of CNS disorders resulting from neurotoxic damage or neurodegenerative diseases, particularly those CNS disorders

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.