Compounds > 2-Methyl-4-quinolinol
Page last updated: 2024-12-06

2-Methyl-4-quinolinol

2-Methyl-4-quinolinol, also known as 4-hydroxy-2-methylquinoline, is a heterocyclic organic compound with a quinoline core. It is a white to pale yellow solid that is soluble in most organic solvents. 2-Methyl-4-quinolinol has been investigated for its potential biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. Research has shown that it exhibits significant antibacterial activity against Gram-positive bacteria, such as Staphylococcus aureus. Its anti-inflammatory properties have been attributed to its ability to inhibit the production of inflammatory mediators. The compound's anticancer potential is being explored due to its ability to induce apoptosis in cancer cells. The synthesis of 2-Methyl-4-quinolinol often involves the condensation of aniline derivatives with β-ketoesters. Studies on 2-Methyl-4-quinolinol aim to further understand its pharmacological properties, explore its potential as a drug candidate, and develop more effective therapeutic agents for various diseases.'

Cross-References

ID SourceID
PubMed CID69089
CHEMBL ID1256109
CHEBI ID194391
SCHEMBL ID266459

Synonyms (65)

Synonym
2-methyl-quinolin-4-ol
2-methylquinolin-4-ol
4-hydroxy-2-methylquinoline
4-hydroxyquinaldine
607-67-0
nsc-21483
2-methyl-4-quinolinol
4-quinolinol, 2-methyl-
nsc21483
OPREA1_457343
OPREA1_710493
MLS000084685
smr000019032
C1269
1h-4-oxoquinaldine
KUC100216N
SR-01000620630-2
4-hydroxy-2-methylquinoline, 98.5%
MAYBRIDGE1_000216
2-methylquinolin-4(1h)-one
STK024344
STK054930
inchi=1/c10h9no/c1-7-6-10(12)8-4-2-3-5-9(8)11-7/h2-6h,1h3,(h,11,12)
nwiniegdlhhnlh-uhfffaoysa-
AKOS000265038
HMS542B18
FT-0694543
2-methyl-1h-quinolin-4-one
CHEBI:194391
AKOS003238098
A8457
AH-034/32851007
5660-24-2
nsc 21483
einecs 210-140-6
CHEMBL1256109
CCG-44041
HMS2364A23
FT-0618748
2-methyl-4-hydroxyquinoline
SCHEMBL266459
AB00404214-09
J-650319
TS-02117
Q-102032
2-methyl-1,4-dihydroquinolin-4-one
M2620
DTXSID40209515
F0451-0420
mfcd00006758
ZB0110
SY048580
F16203
C21873
AMY23277
mfcd00518775
CS-0019244
D82318
SB67513
SB67949
VFH ,
2-methyl-quinolin-4(1h)-one
EN300-129304
CS-0159505
Z445211720
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quinolinesA class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring.
[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]

Pathways (2)

PathwayProteinsCompounds
aurachin RE biosynthesis618
aurachin A, B, C and D biosynthesis1026

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency79.43280.044717.8581100.0000AID485294
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency7.07950.036619.637650.1187AID2100
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency2.05960.00419.984825.9290AID504444
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID517486Passive transcellular permeability of the compound at pH 4 by PAMPA2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517484Lipophilicity, log D of the compound at pH 7.42010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517485Passive transcellular permeability of the compound at pH 7.4 by PAMPA2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517479Resistant index. ratio of EC50 for chloroquine, mefloquine, pyrimethamine and atovaquone-resistant Plasmodium falciparum TM90-C2B to EC50 for chloroquine and pyrimethamine-resistant Plasmodium falciparum W22010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517478Antimalarial activity against chloroquine, mefloquine, pyrimethamine and atovaquone-resistant Plasmodium falciparum TM90-C2B infected in human A+ erythrocytes after 72 hrs by SYBR Green I assay2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517482Cytotoxicity index, ratio of EC50 for mice (Mus musculus) J774 cells to EC50 for chloroquine, mefloquine, pyrimethamine and atovaquone-resistant Plasmodium falciparum TM90-C2B2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517481Cytotoxicity against mouse J774 cells2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517483Aqueous solubility of the compound at pH 7.4 by HPLC analysis2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
AID517480Antimalarial activity against chloroquine and pyrimethamine-resistant Plasmodium falciparum W2 infected in human A+ erythrocytes after 72 hrs by SYBR Green I assay2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.
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.
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[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's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's5 (62.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.08

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 Index12.08 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.28 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.08)

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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0510aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
atovaquone
Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.		2.0510hydroxy-1,2-naphthoquinone
3-heptyl-4-hydroxy-7-methoxy-2-methylquinoline
3-heptyl-4-hydroxy-7-methoxy-2-methylquinoline: structure given in first source		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110
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