319-69-7

Usage

Uses

Used in Pharmaceutical Industry:
(5-fluoro-1H-indol-3-yl)acetic acid ethyl ester is used as a lead compound for the development of new pharmaceuticals due to its potential biological activities and improved solubility and bioavailability.
Used in Medicinal Chemistry Research:
(5-fluoro-1H-indol-3-yl)acetic acid ethyl ester is used as a research compound for exploring its anti-cancer, anti-inflammatory, and anti-microbial properties, which could contribute to the advancement of drug discovery and development.
Used in Drug Delivery Systems:
(5-fluoro-1H-indol-3-yl)acetic acid ethyl ester may be utilized in the design of drug delivery systems to enhance the efficacy and bioavailability of pharmaceuticals, particularly in the context of targeted therapies and personalized medicine.
Used in Chemical Industry:
(5-fluoro-1H-indol-3-yl)acetic acid ethyl ester is used as a chemical intermediate for the synthesis of various compounds with potential applications in different sectors, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 399-52-0 5-fluoro-1H-indole 
• 105-36-2 ethyl bromoacetate 
• 847-07-4 ethyl 2-(ethoxycarbonyl)-5-fluoro-1H-indole-3-acetate 
• 132623-10-0 2-carboxy-5-fluoro-1H-indole-3-acetic acid 
• 371-40-4 4-fluoroaniline 
• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 221188-43-8 (1-benzyl-5-fluoro-1H-indol-3-yl)-acetic acid ethyl ester 
• 443-73-2 (5-fluoroindol-3-yl)acetic acid 
• 221188-42-7 ethyl <1-(4-fluorophenyl)-5-fluoroindol-3-yl>acetate 

Relevant academic research and scientific papers

Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer

Fe, Co, and Mn hydride-initiated radical olefin additions have enjoyed great success in modern synthesis, yet the extension of other hydrogen radicalophiles instead of olefins remains largely elusive. Herein, we report an efficient Fe-catalyzed intramolec

Myoglobin-Catalyzed C?H Functionalization of Unprotected Indoles

Functionalized indoles are recurrent motifs in bioactive natural products and pharmaceuticals. While transition metal-catalyzed carbene transfer has provided an attractive route to afford C3-functionalized indoles, these protocols are viable only in the presence of N-protected indoles, owing to competition from the more facile N?H insertion reaction. Herein, a biocatalytic strategy for enabling the direct C?H functionalization of unprotected indoles is reported. Engineered variants of myoglobin provide efficient biocatalysts for this reaction, which has no precedents in the biological world, enabling the transformation of a broad range of indoles in the presence of ethyl α-diazoacetate to give the corresponding C3-functionalized derivatives in high conversion yields and excellent chemoselectivity. This strategy could be exploited to develop a concise chemoenzymatic route to afford the nonsteroidal anti-inflammatory drug indomethacin.

A Cooperative Hydrogen Bond Donor–Br?nsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans

Carbocations stabilized by adjacent oxygen atoms are useful reactive intermediates involved in fundamental chemical transformations. These oxocarbenium ions typically lack sufficient electron density to engage established chiral Br?nsted or Lewis acid catalysts, presenting a major challenge to their widespread application in asymmetric catalysis. Leading methods for selectivity operate primarily through electrostatic pairing between the oxocarbenium ion and a chiral counterion. A general approach to new enantioselective transformations of oxocarbenium ions requires novel strategies that address the weak binding capabilities of these intermediates. We demonstrate herein a novel cooperative catalysis system for selective reactions with oxocarbenium ions. This new strategy has been applied to a highly selective and rapid oxa-Pictet–Spengler reaction and highlights a powerful combination of an achiral hydrogen bond donor with a chiral Br?nsted acid.

TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF

The present invention is directed to substituted indole compounds of formula (I) which are tropomyosin-related kinase (Trk) family protein kinase inhibitors, and hence are useful in the treatment of pain, inflammation, cancer, restenosis, atherosclerosis, psoriasis, thrombosis, adisease, disorder, injury, or malfunction relating to dysmyelination or demyelination or a disease or disorder associated with abnormal activities of nerve growth factor (NGF) receptor TrkA.

Tert-Butyl Iodide Mediated Reductive Fischer Indolization of Conjugated Hydrazones

A novel reductive Fischer indolization of readily available N-aryl conjugated hydrazones with tert-butyl iodide has been developed. In this reaction, tert-butyl iodide is used as anhydrous HI source, and the generated HI acts as a Br?nsted acid and a reducing agent. This operationally simple method allows access to various indole derivatives. Furthermore, the procedure can be applied to the synthesis of biologically active compounds.

Discovery and refinement of a new structural class of potent peptide deformylase inhibitors

New classes of antibiotics are urgently needed to counter increasing levels of pathogen resistance. Peptide deformylase (PDF) was originally selected as a specific bacterial target, but a human homologue, the inhibition of which causes cell death, was rec

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.