521074-55-5

Basic information

• Product Name: 7-amino-8-methylquinoline-3-carbaldehyde
• Synonyms: 7-amino-8-methylquinoline-3-carbaldehyde;7-Amino-8-methyl-3-quinolinecarboxaldehyde
• CAS NO: 521074-55-5
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.213
• Mol File: 521074-55-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 405.758°C at 760 mmHg
• Flash Point: 199.195°C
• Appearance: /
• Density: 1.266
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: 7-amino-8-methylquinoline-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 7-amino-8-methylquinoline-3-carbaldehyde(521074-55-5)
• EPA Substance Registry System: 7-amino-8-methylquinoline-3-carbaldehyde(521074-55-5)

Safety Data

• Hazardous Substances Data: 521074-55-5(Hazardous Substances Data)

Usage

General Description

7-amino-8-methylquinoline-3-carbaldehyde is a chemical compound with a molecular formula C11H10N2O. It belongs to the class of quinoline derivatives and is used in organic synthesis and pharmaceutical research. 7-amino-8-methylquinoline-3-carbaldehyde has a quinoline core with an attached carbaldehyde group and an amino group at the 7th and 8th positions, respectively. Its structure and functionality make it a versatile building block in the synthesis of various organic compounds and potential drug candidates. Additionally, the presence of the carbaldehyde group makes it an important intermediate in the production of dyes and pigments. Overall, 7-amino-8-methylquinoline-3-carbaldehyde is an important chemical in the field of organic chemistry and has potential applications in various industries.

InChI:InChI=1/C11H10N2O/c1-7-10(12)3-2-9-4-8(6-14)5-13-11(7)9/h2-6H,12H2,1H3

Upstream product

• 823-40-5 2,6-toluenediamine 

Downstream Products

• 521072-94-6 4-butoxy-N-[8-methyl-3-(pyrrolidin-1-ylmethyl)quinolin-7-yl]benzamide 
• 1373823-34-7 4-(cyclopropylmethoxy)-N-{3-[(1S)-1-hydroxyethyl]-8-methylquinolin-7-yl}benzamide 
• 1190044-19-9 4-(cyclopropylmethoxy)-N-[3-(1-hydroxyethyl)-8-methylquinolin-7-yl]benzamide 
• 1373823-33-6 3-bromo-N-[8-methyl-3-(1-pyrrolidin-1-ylethyl)quinolin-7-yl]benzamide 
• 1373823-10-9 3-bromo-N-[8-methyl-3-(1-pyrrolidin-1-ylethyl)quinolin-7-yl]benzamide 
• 1190117-16-8 N-[3-(1-chloroethyl)-8-methylquinolin-7-yl ]-4-(cyclopropylmethoxy)benzamide 
• 1373823-27-8 4-(cyclopropylmethoxy)-N-(3-{1-[(2-hydroxy-2-methylpropyl)amino]ethyl}-8-methylquinolin-7-yl)benzamide 
• 1373823-26-7 4-(cyclopropylmethoxy)-N-(3-{1-[(2-hydroxyethyl)amino]-ethyl}-8-methylquinolin-7-yl)benzamide 
• 1373823-25-6 4-(cyclopropylmethoxy)-N-(3-{1-[(3S)-3-hydroxypyrrolidin-1-yl]ethyl}-8-methylquinolin-7-yl)benzamide 
• 1373823-24-5 4-(cyclopropylmethoxy)-N-{8-methyl-3-[1-(4-methylpiperazin-1-yl)ethyl]quinolin-7-yl}benzamide 
• 1373823-23-4 N-[3-(1-azepan-1-ylethyl)-8-methylquinolin-7-yl]-4-(cyclopropylmethoxy)benzamide 
• 1373823-22-3 4-(cyclopropylmethoxy)-N-[8-methyl-3-(1-piperidin-1-ylethyl)quinolin-7-yl]benzamide 
• 1373823-21-2 4-(cyclopropylmethoxy)-N-{8-methyl-3-[(2-methylpyrrolidin-1-yl)methyl]quinolin-7-yl}benzamide 
• 521073-84-7 5-(4-fluorophenyl)-N-[8-methyl-3-(pyrrolidin-1-ylmethyl)-quinolin-7-yl]pentanamide 

Relevant articles and documents

Synthesis, structure-activity relationship, and pharmacological studies of novel melanin-concentrating hormone receptor 1 antagonists 3- aminomethylquinolines: Reducing human ether-a-go-go-related gene (hERG) associated liabilities

Recently, we discovered 3-aminomethylquinoline derivative 1, a selective, highly potent, centrally acting, and orally bioavailable human MCH receptor 1 (hMCHR1) antagonist, that inhibited food intake in F344 rats with diet-induced obesity (DIO). Subsequent investigation of 1 was discontinued because 1 showed potent hERG K+ channel inhibition in a patch-clamp study. To decrease hERG K+ channel inhibition, experiments with ligand-based drug designs based on 1 and a docking study were conducted. Replacement of the terminal p-fluorophenyl group with a cyclopropylmethoxy group, methyl group introduction on the benzylic carbon at the 3-position of the quinoline core, and employment of a [2-(acetylamino)ethyl]amino group as the amine portion eliminated hERG K+ channel inhibitory activity in a patch-clamp study, leading to the discovery of N-{3-[(1R)-1-{[2-(acetylamino)ethyl]amino} ethyl]-8-methylquinolin-7-yl}-4-(cyclopropylmethoxy)benzamide (R)-10h. The compound (R)-10h showed potent inhibitory activity against hMCHR1 and dose-dependently suppressed food intake in a 2-day study on DIO-F344 rats. Furthermore, practical chiral synthesis of (R)-10h was performed to determine the molecule's absolute configuration.