54904-22-2

Usage

Uses

Used in Organic Synthesis:
5-Chloroindole-3-propionic acid is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure allows for the development of a wide range of chemical compounds with diverse properties and potential applications.
Used in Chemical Research:
In the field of chemical research, 5-Chloroindole-3-propionic acid serves as a valuable compound for studying the properties and reactions of indole-based structures. Its presence in various chemical reactions can provide insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Pharmaceutical Industry:
5-Chloroindole-3-propionic acid is used as a precursor in the synthesis of pharmaceutical drugs. Its unique structure and potential biological activities make it a promising candidate for the development of new medications with specific therapeutic effects.
Used in Drug Discovery:
5-CHLOROINDOLE-3-PROPIONIC ACID has been studied for its potential biological and pharmacological activities, particularly its effects on the central nervous system. This makes 5-Chloroindole-3-propionic acid a valuable tool in drug discovery, where it can be used to identify and develop new drugs with targeted therapeutic applications.

InChI:InChI=1/C11H10ClNO2/c12-8-2-3-10-9(5-8)7(6-13-10)1-4-11(14)15/h2-3,5-6,13H,1,4H2,(H,14,15)

Upstream product

• 221188-29-0 ethyl 3-(5-chloro-1H-indol-3-yl)propanoate 
• 17422-32-1 5-chloro-1H-indole 
• 79-10-7 acrylic acid 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 54904-18-6 3-(2-carboxyethyl)-5-chloro-1H-indole-2-carboxylic acid 
• 54904-12-0 ethyl 5-chloro-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate 
• 106-47-8 4-chloro-aniline 
• 1421282-90-7 ethyl-3-(5-chloro-1H-indol-3-yl)acrylate 
• 1207962-36-4 3-(5-chloro-1H-indol-3-yl)acrylic acid 
• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 830-96-6 Indole-3-propionic acid 

Downstream Products

• 342636-62-8 Methyl 5-Chloro-1H-indole-3-propionate 
• 1026857-54-4 Methanesulfonic acid 3-[5-chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-propyl ester 
• 170232-12-9 3-[5-Chloro-1-(4-fluorophenyl)-3-1H-indolyl]propanol 
• 170232-13-0 3-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-propionic acid 

Relevant academic research and scientific papers

Sodium Iodide/Hydrogen Peroxide-Mediated Oxidation/Lactonization for the Construction of Spirocyclic Oxindole-Lactones

The sodium iodide/hydrogen peroxide-mediated oxidation/lactonization of indolepropionic acids was achieved, affording the corresponding spirocyclic oxindole-lactones in moderate to high yields. This metal-free procedure features mild reaction conditions, non-toxicity and easy handling, with hydrogen peroxide (H2O2) as a clean oxidant. (Figure presented.).

A Structure-Guided Switch in the Regioselectivity of a Tryptophan Halogenase

Flavin-dependent halogenases are potentially useful biocatalysts for the regioselective halogenation of aromatic compounds. Haloaromatic compounds can be utilised in the synthesis and biosynthesis of pharmaceuticals and other valuable products. Here we report the first X-ray crystal structure of a tryptophan 6-halogenase (SttH), which enabled key residues that contribute to the regioselectivity in tryptophan halogenases to be identified. Structure-guided mutagenesis resulted in a triple mutant (L460F/P461E/P462T) that exhibited a complete switch in regioselectivity; with the substrate 3-indolepropionate 75 % 5-chlorination was observed with the mutant in comparison to 90 % 6-chlorination for the wild-type SttH. This is the first clear example of how regiocomplementary halogenases can be created from a single parent enzyme. The biocatalytic repertoire of SttH was also expanded to include a range of indolic and non-indolic substrates.

Synthesis, characterization, and SAR studies of new (1H-indol-3-yl)alkyl-3- (1H-indol-3-yl)propanamide derivatives as possible antimicrobial and antitubercular agents

In this article, we report herein the SAR studies of a series of (1H-indol-3-yl)alkyl-3-(1H-indol-3-yl)propanamide 10(a-j), 11(a-j). The synthesized compounds were evaluated for their preliminary in vitro antibacterial, antifungal activity and were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. The synthesized compounds displayed interesting antimicrobial activity.

INDOLE AMIDE DERIVATIVES AND RELATED COMPOUNDS FOR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES

This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds.

2-aryl indole derivatives and their use as therapeutic agents

The present invention relates compounds of the formula (I): wherein R1a, R1b; and R2 represent a variety of substituents; R3 represents an optionally substituted phenyl, biphenyl or naphthyl or heteroaryl group; R4 represents hydrogen, C1-6alkyl, carbonyl (=O), (CH2)pphenyl or a C1-2alkylene bridge across the piperidine ring; R5 and R6 each independently represent a variety of substituents; or R5 and R6 together are linked so as to form an optionally substituted 5-or 6-membered ring; X represents an oxygen or a sulfur atom, two hydrogen atoms, ═NH or ═N(C1-6alkyl); Y is a straight or branched C1-4alkylene, C2-4alkenylene or C2-4alkynylene chain; the dotted line represents an optional double bond; m is zero or an integer from 1 to 4; n is an integer from 1 to 4; and p is an integer from 1 to 4; or a pharmaceutically acceptable salt thereof. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migaine, emesis or postherpetic neuralgia.

2-Aryl indole NK1 receptor antagonists: Optimisation of the 2-aryl ring and the indole nitrogen substituent

Novel 2-aryl indole hNK1 receptor ligands were prepared utilising palladium cross-coupling chemistry of a late intermediate as a key step. Compounds with high hNK1 receptor binding affinity and good brain penetration (e.g., 9d) were synthesised.

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.

1-indolyalkyl-4-(alkoxypyrimidinyl)piperazines

Certain 1-indolylalkyl-4-(alkoxypyrimidinyl)piperazines of Formula I are useful antidepressant agents. The STR1 substituents R1, R2 and R5 are hydrogen or lower alkyl; R3 and R4 are hydrogen, alkyl, alkoxy, alkythio, carboxamido, halo, or trifluoromethyl; R6 is alkoxy; and n is the integer 2 or 3.