497258-29-4

Usage

Uses

Used in Research Applications:
1H-Indole-3-acetic acid, 5-fluoro-, methyl ester is used as a research tool for studying the mechanisms of plant growth and development. It helps scientists understand the complex processes that regulate plant behavior and can lead to the discovery of new ways to improve crop yields and resistance to diseases.
Used in Agricultural Applications:
In agriculture, 1H-Indole-3-acetic acid, 5-fluoro-, methyl ester is used to modify the growth and behavior of plants. By manipulating the levels of this synthetic indole auxin, farmers can potentially enhance crop productivity, improve resistance to environmental stressors, and achieve other desirable plant characteristics.
Used in Pharmaceutical and Agrochemical Production:
Due to its unique biological activity, 1H-Indole-3-acetic acid, 5-fluoro-, methyl ester is also utilized in the production of pharmaceuticals and agrochemicals. Its applications in these industries can contribute to the development of new drugs and agricultural products that promote plant health and increase agricultural productivity.

Upstream product

• 67-56-1 methanol 
• 443-73-2 (5-fluoroindol-3-yl)acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 692-29-5 Succinic semialdehyde 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 73139-85-2 2-(5-fluoro-1H-indol-3-yl)acetonitrile 

Downstream Products

• 101349-12-6 2-(5-fluoro-1H-indol-3-yl)ethanol 
• 1412449-51-4 methyl 2-(1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl)acetate 
• 1068968-57-9 2-(3-fluoro-phenyl)-4-methylpyrimidine-5-carboxylic acid [5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide 
• 1068968-55-7 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid [5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide 
• 936252-92-5 2-(3-(5-fluoro-1-(p-toluenesulfonyl)indolyl)ethyloxy)adenosine 
• 936252-76-5 6-chloro-2-(3''-(5''-fluoro-1''-(p-toluenesulfonyl)indolyl)ethyloxy)-3',4',5'-triacetyladenosine 
• 936252-55-0 3-(2-iodoethyl)-5-fluoro-1-(p-toluenesulfonyl)indole 
• 1027596-82-2 2-(5-fluoro-1-tosyl-1H-indol-3-yl)ethyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

COMPOUNDS FOR THE TREATMENT OF HIV

The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

A library of approximately 40 N1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2′-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets.

Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

A library of approximately 40 N1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2′-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets.

NOVEL COMPOUNDS

The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2, R3 and R4 are defined as mentioned in the description, the tautomers thereof, the isomers thereof, the diastereomers thereof, the enantiomers thereof, the hydrates thereof, the mixtures thereof and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, the use thereof and processes for the preparation thereof.

PYRIMIDINE HYDRAZIDE COMPOUNDS AS PGDS INHIBITORS

This invention is directed to a compound wherein R1, R2, R3, R4 and L1 are as defined herein, a pharmaceutical composition comprising the compound, and the use of the compound to treat allergic and/or

INDOLE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to substituted indole compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved.

Structure-activity relationships of 2,N6,5′-substituted adenosine derivatives with potent activity at the A2B adenosine receptor

2, N6, and 5′-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A2BAR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N6-ethyl or N6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-(3-(indolyl)- ethyloxy)adenosine series. Indole 5″- or 6″-halo substitution was favored at the A2BAR, but a 5′-N-ethylcarboxyamide did not further enhance potency. 2-(3″-(6″-Bromoindolyl)ethyloxy)adenosine 28 displayed an A2BAR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5′-N- ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A 2B and A2AARs and a low efficacy partial agonist at A 1 and A3ARs. Thus, we have identified and optimized 2-(2-arylethyl)oxo moieties in AR agonists that enhance A2BAR potency and selectivity.

Aromatic bromination versus oxidation of indolylmalonates by bromine

The reactions of 5-substituted indolylmalonates (2a-e), carrying an electron-withdrawing group at the N(1) position, with bromine in CCl4 or AcOH are reported. These substrates undergo oxidation in competition with the well-known aromatic bromination. Under the two sets of conditions, with parent indolylmalonate (2a), chemospecific oxidation is observed, whereas with 5-hydroxyindolylmalonate (2c), bromination at the 4- and 6-position is the dominating reaction. Investigation of the products composition of several 5-substituted indolylmalonates revealed the following trend: with a 5-substituted electron-withdrawing group like fluorine, the indolylmalonate undergoes oxidation rather than bromination. In contrast, with a 5-substituted electron-donating group, like a hydroxyl group, the ring bromination occurs preferentially over the oxidation. When the 5-substituent is an alkoxyl group, a significant amount of brominated-oxidized products is obtained. Monitoring the oxidation reaction by mass spectrometry allowed the characterization of the 2-bromoindolylidenemalonate intermediate. A bromonium ion is considered as possible pathway in the formation of this intermediate. The conformation of unsymmetrical methoxyl and benzyloxyl substituents was determined from 1H NMR spectra, single-crystal X-ray diffraction and ab initio calculations.