Page last updated: 2024-12-06

4-methylquinolin-2(1H)-one

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Description

4-Methylquinolin-2(1H)-one is a heterocyclic compound that has been investigated for its potential biological activities. Studies have explored its synthesis, which typically involves the condensation of an appropriate aniline derivative with a β-ketoester. The compound has shown antimicrobial activity against various bacterial strains, demonstrating potential as a therapeutic agent. Its fluorescent properties have also made it a subject of research in material science, particularly in the development of organic light-emitting diodes (OLEDs) and sensors. The specific structure of 4-methylquinolin-2(1H)-one, with its methyl group and quinolinone core, contributes to its unique properties and makes it a promising candidate for further exploration in various fields.'

4-methylquinolin-2(1H)-one : A quinolone that is quinolin-2(1H)-one substituted by a methyl group at position 4. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID69088
CHEMBL ID424414
CHEBI ID48986
SCHEMBL ID377555

Synonyms (79)

Synonym
84909-43-3
STL304705
4-methyl-quinolin-2-ol
607-66-9
4-methyl-2-quinolone
2(1h)-quinolinone, 4-methyl-
2-hydroxylepidine
2-lepidinol
nsc2057
carbostyril, 4-methyl-
4-methylquinolin-2-one
2(1h)-lepidinone
4-methyl-2-quinolinol
4-methyl-2(1h)-quinolinone
4-methylcarbostyril
nsc-2057
4-methyl-2-hydroxyquinoline
4-methylquinolin-2-ol
lepidine, 2-hydroxy
OPREA1_780405
SDCCGMLS-0027272.P002
MLS000096591
smr000062448
OPREA1_272485
OPREA1_547052
4-methylquinolin-2(1h)-one
CHEBI:48986 ,
inchi=1/c10h9no/c1-7-6-10(12)11-9-5-3-2-4-8(7)9/h2-6h,1h3,(h,11,12
2-hydroxy-4-methylquinoline, 97%
STK038061
cid_69088
bdbm29214
CHEMBL424414
4-methyl-1h-quinolin-2-one
H0259
HMS1722B17
AKOS001041007
AKOS000120372
A832875
NCGC00036814-07
NCGC00036814-02
NCGC00036814-05
NCGC00036814-04
NCGC00036814-06
NCGC00036814-03
2-hydroxy-4-methylquinoline
nsc 2057
einecs 210-139-0
carbostyril, 4-methyl- (van)
ai3-00843
HMS2320G05
aj2 ,
F0183-0103
FT-0612620
3N-601S
4-methylquinol-2-one
1,2-dihydro-4-methyl-2-oxoquinoline
SCHEMBL377555
DS-1525
CS-0097736
J-515819
mfcd00006745
F0109-0047
F10377
Q27121422
AMY25090
EN300-17147
4-methylquinolin-2-ol;4-methylquinolin-2(1h)-one
BCP33184
DTXSID20976132
O11270
A863869
SB67458
SB67481
SY317482
4-methyl-2-quinolinol 4-methylcarbostyril
mfcd00790771
SY057803
Z56893183
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quinolone
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATAD5 protein, partialHomo sapiens (human)Potency18.35640.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency35.48130.000811.382244.6684AID686979
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
Guanine nucleotide-binding protein GHomo sapiens (human)Potency0.89131.995325.532750.1187AID624287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AromataseHomo sapiens (human)IC50 (µMol)250.46670.00001.290410.0000AID1798975; AID418721
Ribosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)IC50 (µMol)375.23330.00271.62879.9000AID1798975; AID418720
Poly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)IC50 (µMol)12.00000.00210.67505.1300AID748132
[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)
glycogen synthase kinase-3 alphaHomo sapiens (human)AC50300.00000.013529.7434171.7000AID463203
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
negative regulation of chronic inflammatory responseAromataseHomo sapiens (human)
steroid biosynthetic processAromataseHomo sapiens (human)
estrogen biosynthetic processAromataseHomo sapiens (human)
androgen catabolic processAromataseHomo sapiens (human)
syncytium formationAromataseHomo sapiens (human)
negative regulation of macrophage chemotaxisAromataseHomo sapiens (human)
sterol metabolic processAromataseHomo sapiens (human)
female genitalia developmentAromataseHomo sapiens (human)
mammary gland developmentAromataseHomo sapiens (human)
uterus developmentAromataseHomo sapiens (human)
prostate gland growthAromataseHomo sapiens (human)
testosterone biosynthetic processAromataseHomo sapiens (human)
positive regulation of estradiol secretionAromataseHomo sapiens (human)
female gonad developmentAromataseHomo sapiens (human)
response to estradiolAromataseHomo sapiens (human)
quinone catabolic processRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
protein polyubiquitinationPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
Wnt signaling pathwayPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
positive regulation of telomere maintenance via telomerasePoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
protein localization to chromosome, telomeric regionPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
protein poly-ADP-ribosylationPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
protein auto-ADP-ribosylationPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
positive regulation of canonical Wnt signaling pathwayPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
positive regulation of telomere cappingPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
negative regulation of telomere maintenance via telomere lengtheningPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (25)

Processvia Protein(s)Taxonomy
iron ion bindingAromataseHomo sapiens (human)
steroid hydroxylase activityAromataseHomo sapiens (human)
electron transfer activityAromataseHomo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenAromataseHomo sapiens (human)
oxygen bindingAromataseHomo sapiens (human)
heme bindingAromataseHomo sapiens (human)
aromatase activityAromataseHomo sapiens (human)
dihydronicotinamide riboside quinone reductase activityRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
protein bindingRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
zinc ion bindingRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
electron transfer activityRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
oxidoreductase activityRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
oxidoreductase activity, acting on other nitrogenous compounds as donorsRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
chloride ion bindingRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
protein homodimerization activityRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
FAD bindingRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
melatonin bindingRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
resveratrol bindingRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
NAD(P)H dehydrogenase (quinone) activityRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
NAD+ ADP-ribosyltransferase activityPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
protein bindingPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
nucleotidyltransferase activityPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
enzyme bindingPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
metal ion bindingPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
NAD+-protein ADP-ribosyltransferase activityPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
endoplasmic reticulumAromataseHomo sapiens (human)
endoplasmic reticulum membraneAromataseHomo sapiens (human)
membraneAromataseHomo sapiens (human)
endoplasmic reticulumAromataseHomo sapiens (human)
nucleoplasmRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
cytosolRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
extracellular exosomeRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
cytosolRibosyldihydronicotinamide dehydrogenase [quinone]Homo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
Golgi membranePoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
pericentriolar materialPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
chromosome, telomeric regionPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
nucleusPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
nuclear envelopePoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
cytoplasmPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
cytosolPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
perinuclear region of cytoplasmPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
cytoplasmPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
nucleusPoly [ADP-ribose] polymerase tankyrase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID748132Inhibition of auto-PARsylation of GST-tagged TNKS2 PARP domain (947 to 1162) (unknown origin) expressed in Escherichia coli BL21(DE3) after 2 hrs by LC/MS analysis2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Fragment-based ligand design of novel potent inhibitors of tankyrases.
AID418723Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
AID418725Cytotoxicity against human Lu cells after 72 hrs by sulforhodamine B assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
AID418724Cytotoxicity against human LNCAP cells after 72 hrs by sulforhodamine B assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
AID748135Binding affinity to TNKS2 PARP domain (947 to 1162) (unknown origin) expressed in Escherichia coli BL21(DE3) assessed as thermal stabilization at 1 mM by differential scanning flourimetric analysis2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Fragment-based ligand design of novel potent inhibitors of tankyrases.
AID34980Compound was tested for inhibition of crude aldose reductase obtained from rat lens, at the concentration of 100 uM1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Synthesis and aldose reductase inhibitory activity of substituted 2-oxoquinoline-1-acetic acid derivatives.
AID418720Inhibition of human quinone reductase 2 expressed in Escherichia coli BL21(DE3) incubated at 23 degC by MTT assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
AID418721Inhibition of aromatase after 30 mins by fluorescence assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
AID418722Cytotoxicity against mouse Hepa-1c1c7 cells after 72 hrs by sulforhodamine B assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1798975QR2 Assay and IC50 Value Determination from Article 10.1021/jm801335z: \\Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.\\2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (9.09)18.7374
1990's0 (0.00)18.2507
2000's2 (18.18)29.6817
2010's7 (63.64)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.67

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 Index11.67 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.16 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.67)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]