479422-01-0

Basic information

• Product Name: 4,5-dichloro-2-methyl-1h-indole
• Synonyms: 4,5-dichloro-2-methyl-1h-indole
• CAS NO: 479422-01-0
• Molecular Formula: C₉H₇Cl₂N
• Molecular Weight: 200.06
• Product Categories: Pyrroles & Indoles;Pyrroles & Indoles
• Mol File: 479422-01-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4,5-dichloro-2-methyl-1h-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dichloro-2-methyl-1h-indole(479422-01-0)
• EPA Substance Registry System: 4,5-dichloro-2-methyl-1h-indole(479422-01-0)

Safety Data

• Hazardous Substances Data: 479422-01-0(Hazardous Substances Data)

Usage

General Description

4,5-dichloro-2-methyl-1H-indole is a chemical compound with the molecular formula C9H7Cl2N. It is a substituted indole derivative, which is a heterocyclic compound containing a five-membered ring with a nitrogen atom. 4,5-dichloro-2-methyl-1h-indole is used in pharmaceutical and chemical research as a building block for the synthesis of various drugs and organic compounds. It has also been studied for its potential biological activities, including as an anti-inflammatory agent and in cancer research. 4,5-dichloro-2-methyl-1H-indole is a solid compound that is light sensitive and should be stored and handled with care.

Upstream product

• 19763-90-7 3,4-dichlorophenylhydrazine hydrochloride 
• 57883-13-3 N-(3,4-Dichloro-phenyl)-N'-isopropylidene-hydrazine 

Downstream Products

• 872674-93-6 methyl 4-[[2-(4,5-dichloro-2-methyl-1H-indol-3-yl)ethyl]sulfonyl]benzoate 
• 872675-00-8 methyl 4-[[2-[4,5-dichloro-(1-diphenylmethyl)-2-methyl-1H-indol-3-yl]ethyl]sulfonyl]benzoate 

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.