Page last updated: 2024-11-10

6-nitro-1,4-dihydroquinoxaline-2,3-dione

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

6-nitro-1,4-dihydroquinoxaline-2,3-dione: a fluorescent chemosensor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4038142
CHEMBL ID23044
SCHEMBL ID1259529
SCHEMBL ID14385403
MeSH IDM0537360

Synonyms (31)

Synonym
LS-13399
6-nitro-1,2,3,4-tetrahydroquinoxaline-2,3-dione
EN300-29586
UPCMLD0ENAT5988944:001
OPREA1_565337
AF-615/01046046
6-nitro-2,3-quinoxalinediol
6-nitroquinoxaline-2,3-diol
6-nitro-2,3-dihydroxyquinoxaline, 96%
1,4-dihydro-6-nitroquinoxaline-2,3-dione
6-nitro-1,4-dihydroquinoxaline-2,3-dione
D3241
CHEMBL23044
AKOS000291480
STK664651
AKOS001450188
STK667249
2,3-dihydroxy-6-nitroquinoxaline
6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline
SCHEMBL1259529
SCHEMBL14385403
6-nitro-2,3-quinoxalinediol #
6-nitronaphthalene-2,3-diol
mfcd00450194
6-nitroquinoxaline-2,3(1h,4h)-dione
6-nitro-quinoxaline-2,3-diol
J-015213
Z235352005
6-nitro-1,4-dihydro-quinoxaline-2,3-dione
AMY38405
PD182982
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (16)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor 1Rattus norvegicus (Norway rat)Ki2.00000.00000.41052.7800AID92776
Glutamate receptor 2Rattus norvegicus (Norway rat)Ki2.00000.00000.68536.3000AID92776
Glutamate receptor 3Rattus norvegicus (Norway rat)Ki2.00000.00000.71777.4000AID92776
Glutamate receptor 4Rattus norvegicus (Norway rat)Ki2.00000.00000.52773.5700AID92776
Glutamate receptor ionotropic, kainate 1Rattus norvegicus (Norway rat)IC50 (µMol)15,000.00000.00700.98217.0000AID93561
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)6.05000.00071.600310.0000AID143606; AID144896
Glutamate receptor ionotropic, kainate 2Rattus norvegicus (Norway rat)IC50 (µMol)15,000.00000.00701.01327.0000AID93561
Glutamate receptor ionotropic, kainate 3Rattus norvegicus (Norway rat)IC50 (µMol)15,000.00000.00701.01327.0000AID93561
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)6.05000.00071.630610.0000AID143606; AID144896
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)6.05000.00061.525710.0000AID143606; AID144896
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)6.05000.00071.747210.0000AID143606; AID144896
Glutamate receptor ionotropic, kainate 4Rattus norvegicus (Norway rat)IC50 (µMol)15,000.00000.00701.01327.0000AID93561
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)6.05000.00071.741110.0000AID143606; AID144896
Glutamate receptor ionotropic, kainate 5Rattus norvegicus (Norway rat)IC50 (µMol)15,000.00000.00701.01327.0000AID93561
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)6.05000.00071.741110.0000AID143606; AID144896
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)6.05000.00071.741110.0000AID143606; AID144896
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor 1Rattus norvegicus (Norway rat)Kb3.68500.59003.33007.0000AID147418; AID163310
Glutamate receptor 2Rattus norvegicus (Norway rat)Kb3.68500.59003.17337.0000AID147418; AID163310
Glutamate receptor 3Rattus norvegicus (Norway rat)Kb3.68500.59003.17787.0000AID147418; AID163310
Glutamate receptor 4Rattus norvegicus (Norway rat)Kb3.68500.59003.28567.0000AID147418; AID163310
Glutamate receptor ionotropic, kainate 1Rattus norvegicus (Norway rat)Kb4.60001.29004.96339.0000AID91453
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Kb3.04000.00592.09697.0000AID143296; AID145182
Glutamate receptor ionotropic, kainate 2Rattus norvegicus (Norway rat)Kb4.60001.29004.96339.0000AID91453
Glutamate receptor ionotropic, kainate 3Rattus norvegicus (Norway rat)Kb4.60001.29004.04509.0000AID91453
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Kb3.46670.00592.41137.0000AID143296; AID145182
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Kb3.46670.00592.41137.0000AID143296; AID145182
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Kb3.46670.00592.41137.0000AID143296; AID145182
Glutamate receptor ionotropic, kainate 4Rattus norvegicus (Norway rat)Kb4.60001.29004.96339.0000AID91453
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Kb3.46670.00592.41137.0000AID143296; AID145182
Glutamate receptor ionotropic, kainate 5Rattus norvegicus (Norway rat)Kb4.60001.29004.96339.0000AID91453
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Kb3.46670.00592.41137.0000AID143296; AID145182
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Kb3.46670.00592.41137.0000AID143296; AID145182
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1898594Antischistosomal activity against adult stage of Schistosoma mansoni assessed as inhibition of parasite motility measured after 72 hrs2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
AID143606Displacement of [3H]DCKA at N-methyl-D-aspartate glutamate receptor 11997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors.
AID1898596Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
AID163310Apparent dissociation constant of [3H]AMPA from quisqualate receptor of rat cortical slice1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor.
AID31606Binding affinity against AMPA receptor in rat brain membrane using [3H]-AMPA as radioligand1994Journal of medicinal chemistry, Feb-18, Volume: 37, Issue:4
6-(1H-imidazol-1-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione hydrochloride (YM90K) and related compounds: structure-activity relationships for the AMPA-type non-NMDA receptor.
AID496834Displacement of [3H]AMPA from AMPA receptor in rat cortical membrane2010Journal of medicinal chemistry, Aug-12, Volume: 53, Issue:15
alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists: from bench to bedside.
AID144896Inhibition of [3H]glycine binding to glycine site of N-methyl-D-aspartate glutamate receptor in rat cortical membranes1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor.
AID147418Binding affinity against rat brain Non N-methyl-D-aspartate glutamate receptor glutamate site expressed in Xenopus oocyte1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
Synthesis and structure-activity relationships of substituted 1,4-dihydroquinoxaline-2,3-diones: antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors.
AID143296Binding affinity towards rat brain NMDA receptor glycine site expressed in Xenopus oocyte1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
Synthesis and structure-activity relationships of substituted 1,4-dihydroquinoxaline-2,3-diones: antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors.
AID234072Selectivity for glycine site1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
Synthesis and structure-activity relationships of substituted 1,4-dihydroquinoxaline-2,3-diones: antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors.
AID92343Binding affinity in rat brain cortical membranes by the displacement of [3H]AMPA at Ionotropic glutamate receptor AMPA1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors.
AID1898585Antischistosomal activity against Schistosoma mansoni Puerto-Rican schistosomula assessed as inhibition of parasite motility measured after 72 hrs2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
AID1898595Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
AID145182Apparent dissociation constant of [3H]glycine from N-methyl-D-aspartate glutamate receptor in rat cortical slice preparation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor.
AID92776In vitro inhibition of the specific binding of [3H]AMPA to Ionotropic glutamate receptor AMPA in rat whole brain membranes in the presence of 100 uM KSCN1996Journal of medicinal chemistry, Mar-15, Volume: 39, Issue:6
Novel alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor antagonists: synthesis and structure-activity relationships of 6-(1H-imidazol-1-yl)-7-nitro-2,3(1H,4H)-pyrido[2,3-b]pyrazinedione and related compounds.
AID91453Apparent dissociation constant of [3H]kainate from Ionotropic glutamate receptor ionotropic kainate was determined in rat cortical slice preparation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor.
AID93561Displacement of [3H]kainate from rat brain cortical membrane Ionotropic glutamate receptor kainate1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors.
AID1898617Selectivity index, ratio of CC50 for human HepG2 cells measured after 72 hrs to EC50 for antischistosomal activity against Schistosoma mansoni Puerto-Rican schistosomula measured after 72 hrs2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
AID1898586Antischistosomal activity against Schistosoma mansoni Puerto-Rican schistosomula assessed as phenotypic changes measured after 72 hrs2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
AID1898618Selectivity index, ratio of CC50 for human HepG2 cells measured after 72 hrs to EC50 for antischistosomal activity against adult stage of Schistosoma mansoni measured after 72 hrs2021European journal of medicinal chemistry, Dec-15, Volume: 226Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (62.50)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.03

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.03 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.23 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.03)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]