6127-16-8

Basic information

• Product Name: 4-CHLORO-2-METHYL-1H-INDOLE
• Synonyms: 4-CHLORO-2-METHYL-1H-INDOLE;1H-Indole, 4-chloro-2-methyl-;4-Chloro-2-methylindole
• CAS NO: 6127-16-8
• Molecular Formula: C₉H₈ClN
• Molecular Weight: 165.62
• Mol File: 6127-16-8.mol

Chemical Properties

• Boiling Point: 302.7±22.0 °C(Predicted)
• Appearance: /
• Density: 1.273±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• PKA: 16.67±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-2-METHYL-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-METHYL-1H-INDOLE(6127-16-8)
• EPA Substance Registry System: 4-CHLORO-2-METHYL-1H-INDOLE(6127-16-8)

Safety Data

• Hazardous Substances Data: 6127-16-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-methyl-1H-indole is used as a chemical intermediate for the synthesis of complex organic molecules, particularly in the development of new pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the creation of novel drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro-2-methyl-1H-indole is utilized as a building block for the synthesis of various agrochemicals, contributing to the development of innovative products for crop protection and enhancement of agricultural yields.
Used in Natural Products Synthesis:
4-Chloro-2-methyl-1H-indole is employed as a key intermediate in the synthesis of natural products, facilitating the production of bioactive compounds with potential applications in various fields, including medicine, cosmetics, and food industry.
Used in Medicinal Chemistry Research:
As a compound with demonstrated antineoplastic activity, 4-chloro-2-methyl-1H-indole is used in medicinal chemistry research to explore its potential as a therapeutic agent against various types of cancer. Its unique structure and reactivity make it an interesting candidate for further investigation and development in the field of oncology.

InChI:InChI=1S/C9H8ClN/c1-6-5-7-8(10)3-2-4-9(7)11-6/h2-5,11H,1H3

Upstream product

• 67175-12-6 Aceton-(m-chlor-phenylhydrazon) 
• 791066-15-4 [3-Chloro-2-(2-oxo-propyl)-phenyl]-carbamic acid tert-butyl ester 

Downstream Products

• 872674-90-3 methyl 4-[[2-(4-chloro-2-methyl-1H-indol-3-yl)ethyl]sulfonyl]benzoate 
• 872674-95-8 methyl 4-[[2-[4-chloro-(1-diphenylmethyl)-2-methyl-1H-indol-3-yl]ethyl]sulfonyl]benzoate 
• 6127-20-4 2-(4-chloro-2-methyl-1H-indol-3-yl)acetic acid 

Relevant articles and documents

Inhibition of cytosolic phospholipase A2α: Hit to lead optimization

Compound 1 was previously reported to be a potent inhibitor of cPLA 2α in both artificial monomeric substrate and cell-based assays. However, 1 was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC50 of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzole acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-γ- linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA2α inhibition. The IC50s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA2α and represent well-validated starting points for further optimization.

Substituted indoles as alpha-1 agonists

This invention relates to compounds which are alpha-1 receptor agonists, preferably alpha-1A/L receptor agonists, and which are represented by Formula I: wherein m, A, X, Y, R1, R2, R3, R4 and R5 are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.