911108-90-2

Basic information

• Product Name: 5-hydroxyquinoline-3-carboxylic acid
• Synonyms: 5-hydroxyquinoline-3-carboxylic acid
• CAS NO: 911108-90-2
• Molecular Formula: C10H7NO3
• Molecular Weight: 189.16748
• Mol File: 911108-90-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-hydroxyquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxyquinoline-3-carboxylic acid(911108-90-2)
• EPA Substance Registry System: 5-hydroxyquinoline-3-carboxylic acid(911108-90-2)

Safety Data

• Hazardous Substances Data: 911108-90-2(Hazardous Substances Data)

Usage

General Description

5-hydroxyquinoline-3-carboxylic acid is a chemical compound with the molecular formula C10H7NO3. It is a derivative of quinoline and contains a hydroxy and carboxylic acid functional group. 5-hydroxyquinoline-3-carboxylic acid is used as a building block in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential antioxidant, anti-inflammatory, and anti-cancer properties. Additionally, 5-hydroxyquinoline-3-carboxylic acid has been investigated for its ability to chelate metal ions and its potential use in metal-based drugs. Overall, this chemical compound has a range of potential applications in the fields of medicine, chemistry, and materials science.

Upstream product

• 911108-89-9 methyl 5-methoxyquinoline-3-carboxylate 
• 82673-65-2 N-(2-formyl-3-methoxyphenyl)pivalamide 

Downstream Products

• 911108-83-3 ethyl 5-hydroxyquinoline-3-carboxylate 
• 911108-81-1 5-(benzyloxy)quinoline-3-carboxylic acid 

Relevant articles and documents

Rational design of carbamate-based dual binding site and central AChE inhibitors by a “biooxidisable” prodrug approach: Synthesis, in vitro evaluation and docking studies

Herein, we report a new class of dual binding site AChE inhibitor 4 designed to exert a central cholinergic activation thanks to a redox-activation step of a prodrug precursor 3. Starting from potent pseudo-irreversible quinolinium salts AChE inhibitors 2 previously reported, a new set of diversely substituted quinolinium salts 2a-p was prepared and assayed for their inhibitory activity against AChE. Structure-activity relationship (SAR) analysis of 2a-p coupled with molecular docking studies allowed us to determine which position of the quinolinium scaffold may be considered to anchor the phtalimide fragment presumed to interact with the peripheral anionic site (PAS). In addition, molecular docking provided insight on the linker length required to connect both quinolinium and phatlimide moieties without disrupting the crucial role of quinolinium salt moiety within the catalytic active site (CAS); namely placing the carbamate in the correct position to trigger carbamylation of the active-site serine hydroxyl. Based on this rational design, the putative dual binding site inhibitor 4 and its prodrug 3 were synthesized and subsequently evaluated in vitro against AChE. Pleasingly, whereas compound 4 showed to be a highly potent inhibitor of AChE (IC50 = 6 nM) and binds to AChE-PAS to the same extent as donepezil, its prodrug 3 revealed to be inactive (IC50 > 10 μM). These preliminary results constitute one of the few examples of carbamate-based dual binding site AChE inhibitors.

NEW HETEROCYCLIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS, IN PARTICULAR AS ANTI-ALZHEIMER AGENTS

The invention is related to compound which comprises at least one radical C=Y, Y being O or S, and an oxidable and non protonable nitrogen atom N wherein the distance (d) between the at least one carbon atom of the radical group C=Y and the nitrogen atom, when oxidized, is comprised between 0.3 and 0.8 nanometers. The invention is related to new heterocyclic compounds defined by formula G, their preparation, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly in the treatment of neurodegenerative or Alzheimer disease.