25063-48-3

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 99-09-2 3-nitro-aniline 
• 149-73-5 trimethyl orthoformate 
• 122-51-0 orthoformic acid triethyl ester 
• 15568-86-2 5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 195433-18-2 1-(4-methoxycarbonylbenzyl)-7-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-54-4 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-56-6 1-(2-methoxy-4-methoxycarbonylbenzyl)-7-nitro-4-oxo-1,4-dihydroquinoline 
• 6270-14-0 7-nitroquinolin-4(1H)-one 
• 195433-22-8 7-amino-1-(4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-57-7 5-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-60-2 7-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-67-9 7-amino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 195433-37-5 3-Methoxy-4-(7-nitro-4-oxo-4H-quinolin-1-ylmethyl)-benzoic acid 
• 188244-66-8 2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-7-nitro-4-oxo-1,4-dihydroquinoline 
• 195433-36-4 4-(7-Cyclopentyloxycarbonylamino-4-oxo-4H-quinolin-1-ylmethyl)-benzoic acid 
• 195433-29-5 7-cyclopentyloxycarbonylamino-1-(4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-63-5 2-(1-hydroxy-2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-7-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-62-4 4-[7-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid 

Relevant academic research and scientific papers

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.

Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates

We have synthesized quinolinones with potential antiparasitic and anti-HIV activities by an original two-step method involving microwave irradiation and have evaluated their activities against Plasmodium falciparum, Leishmania donovani, Trichomonas vaginalis, and HIV. None of the tested compounds had been previously described using this method of synthesis. One of the compounds had interesting antiparasitic and anti-HIV activity, which could be improved by substitution with different radicals.

Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones

Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.

Exotic amino acids. 8. Synthesis of monomethyl esters of N-aryl-aminomethylenemalonic acids

N-Arylaminomethyleneisopropylidenemalonates, obtained from ethoxymethyleneisopropylidenemalonate and aromatic amines, underwent methanolysis to form monomethyl esters of N-arylaminomethylenemalonic acids. The conditions of their formation and their yields depend on the nature and positions of the substituents in the aromatic ring of the initial amine.

Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists

This paper describes the synthesis and pharmacological evaluation of three series of compounds 4a-b, 13a-k and 19, structurally related to the known potent cysLT1 receptor antagonists RG-12553, IC1-204219 and ONO-1078, respectively. The common structural feature of these new series is the presence of a 4-quinolone nucleus acting as a template for substitution of the aromatic nucleus present in the prototype antagonists. We describe the evolution of these series leading to antagonists with potency at nanomolar concentrations in vitro.