1092304-85-2

Basic information

• Product Name: 8-BROMOQUINOLIN-2-AMINE
• Synonyms: 8-BROMOQUINOLIN-2-AMINE;8-broMo-2-aMino-quinoline;2-Amino-8-bromoquinoline;8-Bromo-2-quinolinamine
• CAS NO: 1092304-85-2
• Molecular Formula: C9H7BrN2
• Molecular Weight: 223.07
• Mol File: 1092304-85-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 8-BROMOQUINOLIN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BROMOQUINOLIN-2-AMINE(1092304-85-2)
• EPA Substance Registry System: 8-BROMOQUINOLIN-2-AMINE(1092304-85-2)

Safety Data

• Hazardous Substances Data: 1092304-85-2(Hazardous Substances Data)

Usage

General Description

8-Bromoquinolin-2-amine is a chemical compound typically used in organic synthesis and pharmaceutical research. Its molecular formula is C9H6BrN and it has a molar mass of 228.06 g/mol. 8-BROMOQUINOLIN-2-AMINE belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and their derivatives are compounds containing a ring fusion of a benzene to a pyridine ring. This yellow crystalline powder is highly reactive due to the presence of the bromine atom and the amine group, which makes it an important compound in chemical reactions used to create new molecules. It should be handled with care due to its reactivity and potential hazards upon exposure.

Upstream product

• 163485-86-7 8-bromo-2-chloroquinoline 
• 67805-67-8 2-hydroxy-8-bromoquinoline 

Relevant articles and documents

From fragment screening to in vivo efficacy: Optimization of a series of 2-aminoquinolines as potent inhibitors of beta-site amyloid precursor protein cleaving enzyme 1 (bace1)

Using fragment-based screening of a focused fragment library, 2-aminoquinoline 1 was identified as an initial hit for BACE1. Further SAR development was supported by X-ray structures of BACE1 cocrystallized with various ligands and molecular modeling studies to expedite the discovery of potent compounds. These strategies enabled us to integrate the C-3 side chain on 2-aminoquinoline 1 extending deep into the P2′ binding pocket of BACE1 and enhancing the ligand's potency. We were able to improve the BACE1 potency to subnanomolar range, over 106-fold more potent than the initial hit (900 μM). Further elaboration of the physical properties of the lead compounds to those more consistent with good blood-brain barrier permeability led to inhibitors with greatly improved cellular activity and permeability. Compound 59 showed an IC50 value of 11 nM on BACE1 and cellular activity of 80 nM. This compound was advanced into rat pharmacokinetic and pharmacodynamic studies and demonstrated significant reduction of Aβ levels in cerebrospinal fluid (CSF).