157610-83-8

Basic information

• Product Name: N-METHYL-1-QUINOLIN-4-YLMETHANAMINE
• Synonyms: N-METHYL-1-QUINOLIN-4-YLMETHANAMINE;N-methyl-1-quinolin-4-ylmethanamine(SALTDATA: FREE);Methyl(quinolin-4-ylmethyl)amine
• CAS NO: 157610-83-8
• Molecular Formula: C11H12N2
• Molecular Weight: 172.23
• Mol File: 157610-83-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 302.389°C at 760 mmHg
• Flash Point: 136.68°C
• Appearance: /
• Density: 1.087g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: N-METHYL-1-QUINOLIN-4-YLMETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-1-QUINOLIN-4-YLMETHANAMINE(157610-83-8)
• EPA Substance Registry System: N-METHYL-1-QUINOLIN-4-YLMETHANAMINE(157610-83-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 157610-83-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12N2/c1-12-8-9-6-7-13-11-5-3-2-4-10(9)11/h2-7,12H,8H2,1H3

Upstream product

• 67-56-1 methanol 
• 4363-93-3 quinoline-4-carboxaldehyde 
• 74-89-5 methylamine 
• 91-22-5 quinoline 
• 42182-51-4 4-(N-acetyl,N-methylamino)methylquinoline 
• 21233-61-4 quinoline-4-carboxylic acid methyl ester 
• 72802-70-1 4-(N-methylcarboxyamido)-quinoline 
• 1428568-84-6 N-(quinolin-4-ylmethylene)methanamine 

Relevant articles and documents

Base-Promoted Tandem Synthesis of 2-Azaaryl Tetrahydroquinolines

A novel method to synthesize 2-azaaryl tetrahydroquinolines by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives is reported (over 30 examples, yields up to 95%). Mechanistic probe experiments demonstrate that the deprotonation of the benzylic C-H bond and the addition to the styrene vinyl group proceeds via the SNAr mechanism.

Extended structure-activity relationship and pharmacokinetic investigation of (4-quinolinoyl)glycyl-2-cyanopyrrolidine inhibitors of fibroblast activation protein (FAP)

Fibroblast activation protein (FAP) is a serine protease related to dipeptidyl peptidase IV (DPPIV). It has been convincingly linked to multiple disease states involving remodeling of the extracellular matrix. FAP inhibition is investigated as a therapeutic option for several of these diseases, with most attention so far devoted to oncology applications. We previously discovered the N-4-quinolinoyl-Gly-(2S)-cyanoPro scaffold as a possible entry to highly potent and selective FAP inhibitors. In the present study, we explore in detail the structure-activity relationship around this core scaffold. We report extensively optimized compounds that display low nanomolar inhibitory potency and high selectivity against the related dipeptidyl peptidases (DPPs) DPPIV, DPP9, DPPII, and prolyl oligopeptidase (PREP) the log D values, plasma stabilities, and microsomal stabilities of selected compounds were found to be highly satisfactory. Pharmacokinetic evaluation in mice of selected inhibitors demonstrated high oral bioavailability, plasma half-life, and the potential to selectively and completely inhibit FAP in vivo.