161468-33-3

Basic information

• Product Name: 1-AMINO-3-METHYLISOQUINOLINE-4-CARBONITRILE
• Synonyms: 1-AMINO-3-METHYLISOQUINOLINE-4-CARBONITRILE;1-AMino-3-Methyl-4-isoquinolinecarbonitrile
• CAS NO: 161468-33-3
• Molecular Formula: C11H9N3
• Molecular Weight: 183.20926
• Product Categories: Aromatics Compounds;Aromatics;Amines;Heterocycles
• Mol File: 161468-33-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 273-274°C
• Boiling Point: 398.7 °C at 760 mmHg
• Flash Point: 194.9 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 1.44E-06mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Refrigerator
• Solubility: DMF, DMSO
• CAS DataBase Reference: 1-AMINO-3-METHYLISOQUINOLINE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-3-METHYLISOQUINOLINE-4-CARBONITRILE(161468-33-3)
• EPA Substance Registry System: 1-AMINO-3-METHYLISOQUINOLINE-4-CARBONITRILE(161468-33-3)

Safety Data

• Hazardous Substances Data: 161468-33-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Powder

InChI:InChI=1/C11H9N3/c1-7-10(6-12)8-4-2-3-5-9(8)11(13)14-7/h2-5H,1H3,(H2,13,14)

Upstream product

• 161468-31-1 N-(4-cyano-3-methyl-1H-isochromen-1-ylidene)acetamide 
• 124-42-5 acetamidine hydrochloride 
• 3759-28-2 (2-cyanophenyl)acetonitrile 
• 1118-61-2 3-Aminocrotononitrile 
• 874-05-5 3-aminoindazole 

Relevant articles and documents

Cu-Catalyzed Denitrogenative Transannulation of 3-Aminoindazoles to Assemble 1-Aminoisoquinolines and 3-Aminobenzothiophenes

We disclose a novel Cu-catalyzed denitrogenative transannulation of 3-aminoindazoles to afford diverse functionalized 3-aminobenzothiophenes and 1-aminoisoquinolines, in which denitrogenative transannulation of 3-aminoindazoles is reported for the first t

Antimalarial activity of novel 4-cyano-3-methylisoquinoline inhibitors against: Plasmodium falciparum: Design, synthesis and biological evaluation

Central to malaria pathogenesis is the invasion of human red blood cells by Plasmodium falciparum parasites. Following each cycle of intracellular development and replication, parasites activate a cellular program to egress from their current host cell and invade a new one. The orchestration of this process critically relies upon numerous organised phospho-signaling cascades, which are mediated by a number of central kinases. Parasite kinases are emerging as novel antimalarial targets as they have diverged sufficiently from their mammalian counterparts to allow selectable therapeutic action. Parasite protein kinase A (PfPKA) is highly expressed late in the cell cycle of the parasite blood stage and has been shown to phosphorylate a critical invasion protein, Apical Membrane Antigen 1. This enzyme could therefore be a valuable drug target so we have repurposed a substituted 4-cyano-3-methylisoquinoline that has been shown to inhibit rat PKA with the goal of targeting PfPKA. We synthesised a novel series of compounds and, although many potently inhibit the growth of chloroquine sensitive and resistant strains of P. falciparum, they were found to have minimal activity against PfPKA, indicating that they likely have another target important to parasite cytokinesis and invasion.

Acetylation of α-cyano-o-tolunitrile: Reinvestigation and convenient synthesis of isoquinolines

The product from the diacetylation of α-cyano-o-tolunitrile has now been assigned as an isocoumarin derivative. This is readily transformed into various 1-substituted-3-methylisoquinoline-4-carbonitriles by reaction with oxygen, nitrogen, carbon and hydrogen nucleophiles.