Compounds > 1-hydroxy-2-dodecyl-4(1h)quinolone
Page last updated: 2024-11-08

1-hydroxy-2-dodecyl-4(1h)quinolone

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Description

1-hydroxy-2-dodecyl-4(1H)quinolone: inhibits alternative NADH dehydrogenase; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID600305
CHEMBL ID224182
SCHEMBL ID8535434
MeSH IDM0511923

Synonyms (12)

Synonym
(1-hydroxy-2-dodecyl-4(1h)quinolone)
2-dodecyl-1-hydroxy-quinolin-4-one
CHEMBL224182 ,
1-hydroxy-2-dodecyl-4-(1h)quinoline
1-hydroxy-2-dodecyl-4(1h)quinoline
bdbm50203194
1-hydroxy-2-dodecyl-4(1h)quinolone
2-dodecyl-1-hydroxyquinolin-4-one
SCHEMBL8535434
2-dodecyl -4-hydroxy quinoline n-oxide
2-dodecyl-1-oxidanidyl-quinolin-1-ium-4-ol
PD179582
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase Plasmodium falciparum (malaria parasite P. falciparum)IC50 (µMol)4.00000.23002.64439.4800AID370979
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID285496Inhibition of invasion of Toxoplasma gondii RH in human foreskin fibroblasts assessed as decreased infection rate pretreated with 1 to 1000 nM after 2 hrs before infection2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID285501Effect on Toxoplasma gondii RH growth in human foreskin fibroblasts incubated with 0.1 uM for 24 hrs assessed as recovery after 72 hrs without drug2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID285498Reduced parasitaemia in Plasmodium falciparum FCBR ring stage parasites2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID370979Inhibition of Plasmodium falciparum DHOD2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors.
AID495502Antimicrobial activity against Toxoplasma gondii type 1 RH strain infected in human foreskin fibroblasts monolayer assessed as inhibition of parasite replication after 24 hrs by phase-contrast microscopy2010Antimicrobial agents and chemotherapy, Jan, Volume: 54, Issue:1
In vitro and in vivo activities of 1-hydroxy-2-alkyl-4(1H)quinolone derivatives against Toxoplasma gondii.
AID285504Effect on Toxoplasma gondii RH growth in human foreskin fibroblasts incubated with 0.1 uM for 24 hrs after 6 hrs postinfection assessed as recovery after 72 hrs without drug2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID370980Inhibition of Saccharomyces cerevisiae DHOD2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors.
AID285497Inhibitory effect on metabolic activity of HFF cells upto 10 uM by Alamar Blue assay2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID495505Antimicrobial activity against GFP-expressing Toxoplasma gondii type 1 RH strain ip infected in NMRI mouse assessed as decrease in parasite DNA level in liver at 32 mg/kg, ip administered 3 days postinfection for 5 days by quantitative PCR analysis2010Antimicrobial agents and chemotherapy, Jan, Volume: 54, Issue:1
In vitro and in vivo activities of 1-hydroxy-2-alkyl-4(1H)quinolone derivatives against Toxoplasma gondii.
AID370981Antimalarial activity against Plasmodium falciparum DD2 by [3H]hypoxanthine uptake2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors.
AID285503Effect on Toxoplasma gondii RH growth in human foreskin fibroblasts incubated with 0.1 uM for 24 hrs after 6 hrs postinfection assessed as recovery after 72 hrs without drug2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID370978Inhibition of Plasmodium falciparum NDH22009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors.
AID664858Inhibition of recombinant Plasmodium falciparum NDH2 expressed in Escherichia coli ANN0222 by spectrophotometry2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Identification of novel antimalarial chemotypes via chemoinformatic compound selection methods for a high-throughput screening program against the novel malarial target, PfNDH2: increasing hit rate via virtual screening methods.
AID495504Antimicrobial activity against GFP-expressing Toxoplasma gondii type 1 RH strain ip infected in NMRI mouse assessed as decrease in infected peritoneal cells in peritoneal cavity lavage at 32 mg/kg, ip administered 3 days postinfection for 5 days2010Antimicrobial agents and chemotherapy, Jan, Volume: 54, Issue:1
In vitro and in vivo activities of 1-hydroxy-2-alkyl-4(1H)quinolone derivatives against Toxoplasma gondii.
AID285499Inhibition of Plasmodium falciparum trophozoite replication after 36 hrs by fluorometric assay2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID285494Inhibition of Toxoplasma gondii RH replication in human foreskin fibroblasts incubated for 24 hrs with drug after 2 hrs postinfection by immunofluorescence microscopy2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID370982Antimalarial activity against Plasmodium falciparum DD2 expressing Saccharomyces cerevisiae DHOD by [3H]hypoxanthine uptake2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors.
AID285505Inhibition of Toxoplasma gondii RH replication in human foreskin fibroblasts incubated for 24 hrs with drug after 36 hrs postinfection by immunofluorescence microscopy2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID285495Inhibition of Toxoplasma gondii lacZ-transfected RH strain in in human foreskin fibroblasts assessed as beta galactosidase activity after 30 hrs by colorimetric assay2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID285500Susceptibility of Toxoplasma gondii lacZ-transfected RH strain in human foreskin fibroblasts assessed as growth at 0.1 uM to 0.01 uM after 30 hrs by colorimetric assay2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
AID285502Effect on Toxoplasma gondii RH growth in human foreskin fibroblasts incubated with 1 uM for 24 hrs assessed as recovery after 72 hrs without drug2007Antimicrobial agents and chemotherapy, Apr, Volume: 51, Issue:4
Growth inhibition of Toxoplasma gondii and Plasmodium falciparum by nanomolar concentrations of 1-hydroxy-2-dodecyl-4(1H)quinolone, a high-affinity inhibitor of alternative (type II) NADH dehydrogenases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's4 (57.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.36

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 Index12.36 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.36)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenol
[no description available]		2.0510phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
vitamin k 3
Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.		2.05101,4-naphthoquinones;
vitamin K		angiogenesis inhibitor;
antineoplastic agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
human urinary metabolite;
nutraceutical
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		3.1650monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
rotenone
Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.		2.0510organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
mitochondrial NADH:ubiquinone reductase inhibitor;
phytogenic insecticide;
piscicide;
toxin
indophenol
Indophenol: A deep blue dye (with the formula OC6H4NC6H4OH) used to detect AMMONIA in a common test called the Berthelot's reaction and to detect PARACETAMOL by spectrophotometry.. indophenol : A quinone imine obtained by formal condensation of one of the keto groups of benzoquinone with the amino group of 4-hydroxyaniline.		2.0510quinone iminedye
flavone
flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.		2.0510flavonesmetabolite;
nematicide
diphenyliodonium
diphenyliodonium: RN given refers to the parent coumpound; inhibitor of neutrophil superoxide generating oxidase; structure has been determined		2.0510
2,6-dichloroindophenol
2,6-Dichloroindophenol: A dye used as a reagent in the determination of vitamin C.. 2,6-dichloroindophenol : A quinone imine that is indophenol substituted by chloro groups at positions 2 and 6.. N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine : 1,4-benzoquinone imine having a 3,5-dichloro-4-hydroxyphenyl substituent attached to the nitrogen atom.		2.0510dichlorobenzene;
quinone imine
antimycin a
[no description available]		2.0510benzamides;
formamides;
macrodiolide;
phenols		antifungal agent;
mitochondrial respiratory-chain inhibitor;
piscicide
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.		2.7430hydroxy-1,2-naphthoquinone
diphenyleneiodium chloride
dibenziodolium chloride : An organic chloride salt having dibenziodolium as the counterion.		2.0510organic chloride saltEC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor;
G-protein-coupled receptor agonist
7-chloro-3-methyl-2-(4-(4-(trifluoromethoxy)benzyl)phenyl)quinolin-4(1h)-one
7-chloro-3-methyl-2-(4-(4-(trifluoromethoxy)benzyl)phenyl)quinolin-4(1H)-one: an antimalarial; structure in first source		2.2110
ConditionIndicatedRelationship StrengthStudiesTrials
Central Nervous System Toxoplasmosis
[description not available]		02.0510
Toxoplasmosis, Animal
Acquired infection of non-human animals by organisms of the genus TOXOPLASMA.		02.0510
Toxoplasmosis, Cerebral
Infections of the BRAIN caused by the protozoan TOXOPLASMA gondii that primarily arise in individuals with IMMUNOLOGIC DEFICIENCY SYNDROMES (see also AIDS-RELATED OPPORTUNISTIC INFECTIONS). The infection may involve the brain diffusely or form discrete abscesses. Clinical manifestations include SEIZURES, altered mentation, headache, focal neurologic deficits, and INTRACRANIAL HYPERTENSION. (From Joynt, Clinical Neurology, 1998, Ch27, pp41-3)		02.0510
Plasmodium falciparum Malaria
[description not available]		02.2110
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.		02.2110