1912-45-4

Usage

Uses

Used in Biological Studies:
5-Chloroindole-3-acetic Acid is used as a research tool for studying the selectivity of processes along the auxin response chain. This application is particularly relevant in the field of plant biology, where auxins play a crucial role in regulating growth and development. By using auxin analogs, such as 5-Chloroindole-3-acetic Acid, researchers can gain insights into the specific mechanisms and pathways involved in auxin signaling and response.

InChI:InChI=1/C10H8ClNO2/c11-7-1-2-9-8(4-7)6(5-12-9)3-10(13)14/h1-2,4-5,12H,3H2,(H,13,14)

Upstream product

• 328-50-7 α-ketoglutaric acid 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 221188-28-9 (5-chloro-1H-indol-3-yl)acetic acid ethyl ester 
• 120716-95-2 (2-carboxy-5-chloro-indol-3-yl)-acetic acid 
• 72963-97-4 (2-ethoxycarbonyl-5-chloro-indol-3-yl)-acetic acid ethyl ester 
• 106-47-8 4-chloro-aniline 
• 17422-32-1 5-chloro-1H-indole 
• 81630-83-3 2-(5-chloro-1H-indol-3-yl)acetonitrile 

Downstream Products

• 215998-11-1 5-chloroindole-3-methanol 
• 442883-74-1 5-chloro-3-methylene-2-oxindole 
• 924634-97-9 2-(1-(benzyloxycarbonyl)-5-chloro-1H-indol-3-yl)acetic acid 
• 738608-59-8 1-(2-benzoyl-5-chloro-1H-indol-3-yl)-butan-2-one 
• 924633-70-5 benzyl 3-(3-acetoxy-2-oxopropyl)-5-chloro-1H-indole-1-carboxylate 
• 924634-99-1 benzyl 5-chloro-3-(3-chloro-2-oxopropyl)-1H-indole-1-carboxylate 
• 74339-45-0 methyl 2-(5-chloro-1H-indol-3-yl)acetate 

Relevant academic research and scientific papers

Cyclizations of unsymmetrical bis-1,2-(3-indolyl)ethanes: Synthesis of (-)-tjipanazole F1

The inter- and intramolecular dimerization of 3-substituted indoles was studied. The rate and extent of dimerization depends on the indole substituents. The intramolecular dimerization of unsymmetrical bis-1,2-(3-indolyl)ethanes could be controlled using either thermodynamic reaction conditions (neat trifluoroacetic acid) or kinetic conditions (2 equiv acid/chloroform). This control of regiochemistry has been applied to an efficient synthesis of (-)- tjipanazole F1.

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst

Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.

A substituted indole -3 - acetic acid synthesis method (by machine translation)

The present invention provides a substituted indole - 3 - acetic acid synthesis method, comprises the following steps: (1) in order to replace the indole as the starting material, with the acylation reagent under the action of catalyst through the tutor - acylation to obtain the 1, 3 - diacetyl substituted indole; (2) intermediate 1, 3 - diacetyl substituted indole does not need refining, directly with the morpholine and sulfur by the Willgerodt - Kindler rearrangement reaction, the inorganic under the catalysis of alkali hydrolysis, acidified to obtain substituted indole - 3 - acetic acid. (by machine translation)

Indole-3-acetic acid derivatives

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from H or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups, lower alkoxy groups, aryl groups or aryloxy groups, wherein at least one of R4, R5, R6 and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT.

Use of indole-3-acetic acid derivatives in medicine

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT

USE OF INDOLE-3-ACETIC ACID DERIVATIVES IN MEDICINE

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R'3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT

Compounds exhibiting thrombopoietin-like activities

The compounds of the invention are compounds represented by the following general formula (1): wherein E represents one selected from the group consisting of a methylidyne group and a nitrilo group, R1 represents one selected from the group consisting of optionally substituted aryl groups and optionally substituted heteroaryl groups, R2 represents one selected from the group consisting of a hydrogen atom and alkyl groups, W1 represents an amino acid residue, A represents one selected from the group consisting of a carbonyl group and a sulfonyl group, X1 represents one selected from the group consisting of optionally substituted alkylene groups and optionally substituted alkenylene groups, and p represents 0 or 1; and their pharmacologically acceptable salts, which exhibit thrombopoietin-like activity.

Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy

Substituted indole-3-acetic acid (IAA) derivatives, plant auxins with potential for use as prodrugs in enzyme-prodrug directed cancer therapies, were oxidised with horseradish peroxidase (HRP) and toxicity against V79 Chinese hamster lung fibroblasts was determined. Rate constants for oxidation by HRP compound I were also measured. Halogenated IAAs were found to be the most cytotoxic, with typical surviving fractions of -3 after incubation for 2 h with 100 μM prodrug and HRP.

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.