6270-14-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-7-Nitroquinoline is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
In the field of chemical research, 4-Hydroxy-7-Nitroquinoline serves as a valuable compound for studying the properties and reactions of quinolines. It can be used to investigate the effects of substituents on the reactivity and stability of the molecule, as well as to explore new synthetic routes and methodologies.
Used in Material Science:
4-Hydroxy-7-Nitroquinoline can be employed in the development of new materials with specific properties, such as optical, electronic, or catalytic characteristics. Its incorporation into polymers or other materials can lead to the creation of novel materials with enhanced performance in various applications.
Used in Analytical Chemistry:
As a reference compound or standard, 4-Hydroxy-7-Nitroquinoline can be used in analytical chemistry for the calibration of instruments, the development of new analytical methods, or the identification and quantification of related compounds in complex mixtures. Its distinct spectral properties make it a useful tool in these applications.

InChI:InChI=1/C9H6N2O3/c12-9-3-4-10-8-5-6(11(13)14)1-2-7(8)9/h1-5H,(H,10,12)

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 99-09-2 3-nitro-aniline 
• 40107-10-6 ethyl α-ethoxycarbonyl-β-(m-nitroanilino)acrylate 
• 51726-79-5 7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 25063-48-3 2,2-dimethyl-5-((3-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione 
• 40107-12-8 C₁₀H₅N₂O₅^(1-)*Ag⁽¹⁺⁾ 
• 7248-88-6 7-nitro-4-hydroxy-quinoline-3-carboxylic acid ethylester 
• 40107-11-7 4-hydroxy-7-nitroquinoline-3-carboxylic acid 

Downstream Products

• 40107-14-0 4-amino-7-nitroquinoline 
• 40107-15-1 4,7-diaminoquinoline 
• 658710-27-1 N-(7-nitroquinolin-4-yl)-N-[2-(N,N-dimethylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide 
• 18436-76-5 4-chloro-7-nitroquinoline 

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.

Assembly of 4-aminoquinolines via palladium catalysis: A mild and convenient alternative to SNAr methodology

4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)2/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.

Nitro and amino substitution within the A-ring of 5H-8,9-dimethoxy-5-(2-N, N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: Influence on topoisomerase I-targeting activity and cytotoxicity

Recently, 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3- methylenedioxydibenzo[c,h][1,6]naphthyridin-6-one, 1, was identified as a TOP1-targeting agent with pronounced antitumor activity. In the present study, the effect on activity of substituting a

Structural specificity of chloroquine-hematin binding related to inhibition of hematin polymerization and parasite growth

Considerable data now support the hypothesis that chloroquine (CQ)- hematin binding in the parasite food vacuole leads to inhibition of hematin polymerization and parasite death by hematin poisoning. To better understand the structural specificity of CQ-hematin binding, 13 CQ analogues were chosen and their hematin binding affinity, inhibition of hematin polymerization, and inhibition of parasite growth were measured. As determined by isothermal titration calorimetry (ITC), the stoichiometry data and exothermic binding enthalpies indicated that, like CQ, these analogues bind to two or more hematin μ-oxo dimers in a cofacial π-π sandwich-type complex. Association constants (K(a)'s) ranged from 0.46 to 2.9 x 105 M-1 compared to 4.0 x 105 M-1 for CQ. Remarkably, we were not able to measure any significant interaction between hematin μ-oxo dimer and 11, the 6-chloro analogue of CQ. This result indicates that the 7-chloro substituent in CQ is a critical structural determinant in its binding affinity to hematin μ-oxo dimer. Molecular modeling experiments reinforce the view that the enthalpically favorable π-π interaction observed in the CQ-hematin μ-oxo dimer complex derives from a favorable alignment of the out-of-plane π-electron density in CQ and hematin μ-oxo dimer at the points of intermolecular contact. For 4- aminoquinolines related to CQ, our data suggest that electron-withdrawing functional groups at the 7-position of the quinoline ring are required for activity against both hematin polymerization and parasite growth and that chlorine substitution at position 7 is optimal. Our results also confirm that the CQ diaminoalkyl side chain, especially the aliphatic tertiary nitrogen atom, is an important structural determinant in CQ drug resistance. For CQ analogues 1-13, the lack of correlation between K(a) and hematin polymerization IC50 values suggests that other properties of the CQ-hematin μ-oxo dimer complex, rather than its association constant alone, play a role in the inhibition of hematin polymerization. However, there was a modest correlation between inhibition of hematin polymerization and inhibition of parasite growth when hematin polymerization IC50 values were normalized for hematin μ-oxo dimer binding affinities, adding further evidence that antimalarial 4-aminoquinolines act by this mechanism.

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.