181950-55-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-cyanoquinoline is used as an intermediate in the synthesis of antimalarial drugs and other pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
4-CHLORO-7-CYANOQUINOLINE is also utilized in the production of fungicides and herbicides, serving as an essential intermediate for the creation of effective crop protection agents.
Used in Chemical Synthesis:
4-Chloro-7-cyanoquinoline is a key building block in the synthesis of various biologically active molecules, contributing to the advancement of the chemical industry and the development of novel compounds with diverse applications.

Upstream product

• 2237-30-1 m-cyanoaniline 
• 59551-10-9 diethyl 2-[((3-cyanophenyl)amino)methylene]malonate 
• 63463-18-3 ethyl 7-cyano-4-hydroxyquinoline-3-carboxylate 
• 118078-26-5 7-cyano-4-hydroxyquinoline-3-carboxylic acid 
• 1186230-86-3 4-hydroxyquinoline-7-carbonitrile 
• 1186230-83-0 3-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile 

Downstream Products

• 1253790-96-3 4-aminoquinoline-7-carbonitrile 
• 1491137-42-8 N-benzyl-2-(4-{[(7-cyanoquinolin-4-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)-N-methylacetamide 
• 1491137-40-6 2-(4-{[(7-cyanoquinolin-4-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)-N,N-dicyclohexylacetamide 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUNDS

The present invention relates to compounds of the general formula (1) wherein the variables are defined as given in the description and claims. The invention further relates to uses of and to, processes and intermediates related to compounds of the general formula (I), wherein Q is wherein the substituents of I, Ia and Ib are as defined in description and claims.

Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (log K) and inhibition of β-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, log K values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (π) of the group X. The log K values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% β-hematin inhibitory activity (log BHIA50) was found to correlate with log K and either meta (σm) or para (σp) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that log K values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of β-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible.