57663-18-0

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-Methyl-3H-indole-5-carboxylate is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique chemical structure allows it to be a building block for the development of new medications with diverse therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, Methyl 2-Methyl-3H-indole-5-carboxylate is utilized as a valuable precursor for the creation of complex organic molecules. Its reactivity and functional groups make it suitable for various synthetic pathways, contributing to the advancement of organic chemistry.
Used in Chemical Research:
Methyl 2-Methyl-3H-indole-5-carboxylate is also employed in chemical research to explore its potential biological and pharmacological activities. Studies have indicated its potential as an anti-cancer and antiviral agent, highlighting its importance in the discovery of novel therapeutic agents.
Used in Anticancer Applications:
Methyl 2-Methyl-3H-indole-5-carboxylate is being studied for its potential as an anti-cancer agent, with research focusing on its ability to target and inhibit the growth of cancer cells. Its unique properties may contribute to the development of new cancer treatments.
Used in Antiviral Applications:
In antiviral research, Methyl 2-Methyl-3H-indole-5-carboxylate has shown promise as a potential agent against viral infections. Its ability to interfere with viral replication and pathogenesis makes it a candidate for further investigation in the development of antiviral therapies.

Upstream product

• 67-56-1 methanol 
• 13291-18-4 isopropenylmagnesium bromide 
• 62-23-7 4-nitro-benzoic acid 
• 438003-09-9 methyl 4-nitro-3-(2-oxopropyl)benzoate 
• 24078-21-5 methyl 3-methyl-4-nitrobenzoate 
• 108763-41-3 methyl (E)-3-(2-(dimethylamino)vinyl)-4-nitrobenzoate 
• 142031-67-2 methyl 4-bromo-3-(bromomethyl)benzoate 
• 1338460-69-7 C₁₄H₁₇BrO₂Si 
• 1338460-78-8 methyl 4-bromo-3-(propa-1,2-dien-1-yl)benzoate 
• 55-21-0 benzamide 

Downstream Products

• 206066-79-7 3-(2-chloro-4-phenylbenzyl)-5-methoxycarbonyl-2-methylindole 
• 206066-45-7 3-(biphenyl-4-ylmethyl)-5-(methoxycarbonyl)-2-methylindole 
• 206066-48-0 3-(2-chlorobenzyl)-5-(methoxycarbonyl)-2-methylindole 
• 206066-50-4 3-(2,4-dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylindole 
• 206066-36-6 3-(2,4-dichlorobenzyl)-5-methoxycarbonyl-2-methylindole 
• 206066-52-6 3-(4-benzyloxybenzyl)-5-(methoxycarbonyl)-2-methylindole 
• 438003-12-4 5-(methoxycarbonyl)-2-methyl-3-(4-(2-phenylethenyl)benzyl)indole 
• 1220018-33-6 methyl 1-((2'-(tert-butoxycarbonyl)-[1,1'-biphenyl]-4-yl)methyl)-2-methyl-1H-indole-5-carboxylate 
• 245368-22-3 3-(2-chloro-4-iodobenzyl)-5-(methoxycarbonyl)-2-methylindole 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUND

One of the purposes of the present invention is to provide a heterocyclic derivative that has an IAP (particularly XIAP) binding (inhibiting) activity. Another of the purposes of the present invention is to provide a heterocyclic derivative that has an IAP (particularly XIAP) binding (inhibiting) activity and exhibits a protein degradation induction activity. The present invention provides a compound represented by formula (I) (the symbols in the formula are as defined in the present Description) and salts thereof.

Ring size changes in the development of class I HDAC inhibitors

Five pathways involving different ring structures led to generation of fourteen thienylbenzamides (7–20) which display the structure-activity relationships of class I HDAC inhibitors. All the synthesised compounds inhibit HDAC1 and HDAC2 selectively over other isoforms and many inhibit DLD1 and HCT116 cells more effectively than a parent compound. Compounds 8 and 16 inhibit HCT116 cells by activation of the apoptosis pathway.

Ortho-Bromo(propa-1,2-dien-1-yl)arenes: Substrates for domino reactions

o-Bromo(propa-1,2-dien-1-yl)arenes exhibit novel and orthogonal reactivity under Pd catalysis in the presence of secondary amines to form enamines (concerted Pd insertion, intramolecular carbopalladation, and terminative Buchwald-Hartwig coupling) and of amides to form indoles (addition, Buchwald-Hartwig cyclization, and loss of the acetyl group). The substrates for these reactions can be accessed in a reliable and highly selective two-step process from 2-bromoaryl bromides.

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates

The reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates with formate anions in the presence of Pd(PPh3)4 affords 2-alkylindoles in good to excellent yields.

Intramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines

A thermally induced intramolecular annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined. The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used.

Bartoli indole synthesis on solid supports

(Matrix presented) Bartoli indole synthesis has been performed for the first time on solid supports. Starting from Merrifield resin, immobilization of five nitro benzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic c

Method for inhibiting neoplastic cells with indole derivatives

A method for inhibiting neoplastic cells and related conditions by exposing them to substituted indole derivatives.