21873-49-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Nitroquinolin-4(1H)-one is used as a key building block for the synthesis of pharmaceuticals due to its versatile chemical structure and reactivity. It plays a crucial role in the development of new drugs, particularly in medicinal chemistry, where its unique properties can be harnessed to create novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Nitroquinolin-4(1H)-one serves as a fundamental component in the creation of pesticides and other agricultural chemicals. Its chemical properties make it suitable for the development of compounds that can effectively control pests and diseases in crops, thereby contributing to increased agricultural productivity.
Used in Materials Science:
6-Nitroquinolin-4(1H)-one is also utilized in materials science for the development of new materials with specific properties. Its unique chemical structure allows for the creation of materials with tailored characteristics, such as improved stability, reactivity, or other desirable attributes, which can be applied in various industrial applications.
Used as an Intermediate in Organic Synthesis:
6-Nitroquinolin-4(1H)-one is employed as an intermediate in the production of various organic compounds. Its presence in the synthesis process allows for the formation of a wide range of chemical products, expanding the scope of chemical manufacturing and innovation.

Upstream product

• 100-01-6 4-nitro-aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 103514-53-0 ethyl 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 78596-42-6 ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate 
• 529-37-3 4(1H)-quinolinone 
• 141-82-2 malonic acid 
• 25063-45-0 2,2-dimethyl-5-(((4-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 

Downstream Products

• 68771-39-1 1-methyl-6-nitro-1H-quinolin-4-one 
• 188244-71-5 4-[Methanesulfonyloxy-(1-methyl-6-nitro-4-oxo-1,4-dihydro-quinolin-2-yl)-methyl]-3-methoxy-benzoic acid methyl ester 
• 195433-23-9 6-cyclopentyloxycarbonylamino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 195433-30-8 4-(6-Cyclopentyloxycarbonylamino-1-methyl-4-oxo-1,4-dihydro-quinolin-2-ylmethyl)-3-methoxy-benzoic acid 
• 188244-52-2 4-[6-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid methyl ester 
• 188244-53-3 4-[6-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid 
• 188244-70-4 2-(1-hydroxy-2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-6-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-73-7 2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-6-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-74-8 6-amino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 188244-51-1 6-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 658710-29-3 N-(6-nitroquinolin-4-yl)-N-[2-(N,N-dimethylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide 

Relevant academic research and scientific papers

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels

Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.

Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization

An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.

Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds

A method utilising one or more fluorogenic probes, for the detection of nitroreductase activity. The non-fluorescent probes are reduced in the presence of nitroreductase to form fluorescent derivatives that may be detected using fluorescence spectroscopy. In particular, the method may be used to detect and/or identify a plurality of nitroreductase in a single test environment

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.

Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid

Electron-rich and electron-deficient anilinomethylene derivatives of Meldrum's acid cyclize equally efficiently to quinolin-4-ones via imidoylketene intermediates under flash vacuum pyrolysis (FVP) conditions. Georg Thieme Verlag Stuttgart.

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.

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

Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold - Polymer-bound cyclic malonic acid ester

An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent double substitution with

Preparation of a resin-bound cyclic malonic ester and a facile solid-phase synthesis of 4(1H)quinolones

A resin-bound cyclic malonic ester has been prepared on Merrifield resin. Reaction of the cyclic malonic ester with triethyl orthoformate and subsequent substitution by an arylamine afforded arylaminomethylene cyclic malonic ester preloaded resin. A serie

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.