104711-51-5

Basic information

• Product Name: 5-phenylquinoline-8-amine
• Synonyms: 5-phenylquinoline-8-amine
• CAS NO: 104711-51-5
• Molecular Weight: 220.274
• Mol File: 104711-51-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-phenylquinoline-8-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenylquinoline-8-amine(104711-51-5)
• EPA Substance Registry System: 5-phenylquinoline-8-amine(104711-51-5)

Safety Data

• Hazardous Substances Data: 104711-51-5(Hazardous Substances Data)

Upstream product

• 4964-71-0 5-bromoquinoline 
• 176967-80-9 5-bromo-8-nitroquinoline 
• 170891-76-6 α,α,α-trimethyl-N-(quinolin-8-yl)acetamide 
• 578-66-5 8-amino quinoline 
• 92149-23-0 N-(4-nitro-biphenyl-3-yl)-acetamide 

Relevant articles and documents

Nickel-Catalyzed N, N-Diarylation of 8-Aminoquinoline with Large Steric Aryl Bromides and Fluorescence of Products

A simple and efficient methodology for the synthesis of large sterically hindered triarylamines in a single step was developed. A direct N,N-diarylation of 8-aminoquinoline with sterically hindered bromides, making use of inexpensive nickel as a catalyst and simple sodium salt as a base, gives the products in good to excellent yields. Various bromides and substituted 8-aminoquinolines are tolerated. Preliminary fluorescence results indicate that these sterically hindered and conjugated triarylamines may have some potential in material chemistry.

Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor

Anxiety and depression are common, highly comorbid psychiatric diseases that account for a large proportion of worldwide medical disability. Glyoxalase 1 (GLO1) has been identified as a possible target for the treatment of anxiety and depression. GLO1 is a Zn2+-dependent enzyme that isomerizes a hemithioacetal, formed from glutathione and methylglyoxal, to a lactic acid thioester. To develop active inhibitors of GLO1, fragment-based drug discovery was used to identify fragments that could serve as core scaffolds for lead development. After screening a focused library of metal-binding pharmacophores, 8-(methylsulfonylamino)quinoline (8-MSQ) was identified as a hit. Through computational modeling and synthetic elaboration, a potent GLO1 inhibitor was developed with a novel sulfonamide core pharmacophore. A lead compound was demonstrated to penetrate the blood-brain barrier, elevate levels of methylglyoxal in the brain, and reduce depression-like behavior in mice. These findings provide the basis for GLO1 inhibitors to treat depression and related psychiatric illnesses.