403838-46-0

Basic information

• Product Name: 3-Quinolinecarboxylic acid, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-, ethyl ester
• CAS NO: 403838-46-0
• Molecular Formula: C21H18ClN3O3
• Molecular Weight: 395.845
• Mol File: 403838-46-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-Quinolinecarboxylic acid, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxylic acid, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-, ethyl ester(403838-46-0)
• EPA Substance Registry System: 3-Quinolinecarboxylic acid, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-, ethyl ester(403838-46-0)

Safety Data

• Hazardous Substances Data: 403838-46-0(Hazardous Substances Data)

Upstream product

• 1233518-58-5 Ethyl 8-bromo-4-[(3-chloro-4-methoxybenzyl)amino]-6-cyanoquinoline-3-carboxylate 
• 107-18-6 allyl alcohol 
• 1233518-57-4 ethyl 8-bromo-4-chloro-6-cyanoquinoline-3-carboxylate 
• 4433-63-0 Ethyl boronic acid 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 26832-90-6 diethyl 2-(4-cyanophenylamino)methylenemalonate 
• 41965-95-1 (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride 
• 403841-76-9 4-chloro-6-cyanoquinoline-3-carboxylic acid ethyl ester 

Downstream Products

• 403839-14-5 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-6-cyanoquinoline-3-carboxylic acid pentafluorophenyl ester 
• 403839-11-2 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino ]-6-quinolinecarbonitrile 
• 403839-05-4 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-6-cyano-3-quinolinecarboxylic acid 

Relevant articles and documents

Synthesis and in?vitro evaluation of new fluorinated quinoline derivatives with high affinity for PDE5: Towards the development of new PET neuroimaging probes

The increasing incidence of Alzheimer's disease (AD) worldwide is a major public health problem. Current treatments provide only palliative solutions with significant side effects. Therefore, new efficient treatment options and novel early diagnosis tools are urgently needed. Recently, strong pre-clinical evidences suggested that phosphodiesterase 5 (PDE5) may be clinically relevant both as biomarker and drug-target in AD. In this study, we intended to develop a new radiofluorinated tracer for the visualisation of PDE5 in brain using PET imaging. Based on currently known PDE5 inhibitors, a series of novel fluorinated compounds bearing a quinoline core have been synthesised via multi-steps reaction pathways. Their affinity for PDE5 and selectivity over other PDE families have been investigated. According to the data collected from this in vitro screening, fluorinated derivatives 24a, b bearing a fluoroethoxy group at the C-3 position of the quinoline core appeared to be the most promising structures and will be further radiolabelled with fluorine-18 for in vitro and in vivo evaluations as PET radiotracer for neuroimaging of PDE5.

Quinolines as extremely potent and selective PDE5 inhibitors as potential agents for treatment of erectile dysfunction

In a continuing effort to discover novel chemotypes as potent and selective PDE5 inhibitors for the treatment of male erectile dysfunction (ED), we have found that 4-benzylaminoquinoline derivatives are very potent and selective PDE5 inhibitors. Some compounds in this series had PDE5 IC 50's as low as 50 pM. While an electron withdrawing group at the C6-position of the quinoline substantially improved PDE5 potency, an ethyl group at the C8-position not only improved the PDE5 potency but also the isozyme selectivity. Substitutents at the C3-position can incorporate a variety of different groups. The synthesis and primary structure-activity relationship of this new series of potent PDE5 inhibitors are described.