Compounds > 2-chloro-1,4-naphthoquinone
Page last updated: 2024-12-05

2-chloro-1,4-naphthoquinone

Description

2-Chloro-1,4-naphthoquinone, also known as Chloranil, is a yellow crystalline solid that is widely used as a chemical reagent. It is synthesized by chlorination of 1,4-naphthoquinone. This compound has diverse biological activities, including antifungal, antibacterial, and antiviral properties. It exhibits antitumor activity and acts as an inhibitor of certain enzymes. Its ability to accept electrons makes it a useful reagent in organic synthesis, particularly for oxidation reactions. Due to its versatile applications, it is extensively studied in fields like medicine, agriculture, and materials science.'

2-chloro-1,4-naphthoquinone: Vitamin K dependent carboxylase antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13891
CHEMBL ID349147
CHEBI ID28160
SCHEMBL ID917548
MeSH IDM0144035

Synonyms (46)

Synonym
AC-15235
4-07-00-02425 (beilstein handbook reference)
unii-fof3psj59z
fof3psj59z ,
CHEBI:28160 ,
brn 1867045
1,4-naphthoquinone, 2-chloro-
einecs 213-776-2
nsc 400597
1,4-naphthalenedione, 2-chloro-
2-chloronaphthalene-1,4-dione
nsc-400597
nsc400597
wln: l66 bv evj cg
2-chloronaphthoquinone
C03753
2-chloro-1,4-naphthoquinone
1010-60-2
AKOS006343761
FT-0695969
2-chloro-[1,4]naphthoquinone
CHEMBL349147
2-chloranylnaphthalene-1,4-dione
A800322
FT-0611685
2-chloro-1,4-naphthalenedione
FD7245
AM84303
2-chloro-1,4-naphthquinone
mfcd00029187
SCHEMBL917548
W-108929
C2721
DTXSID00143623
GS-3324
2-chloro-1,4-dihydronaphthalene-1,4-dione
chloronaphthoquinone
SY051032
96843-34-4
Q27103536
2-chloronaphthalene-1,4-dione (2-chloro-1,4-naphthoquinone)
2-chlor-1,4-naphthochinon
CS-0034824
PD099119
HY-115243
EN300-6490914
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
1,4-naphthoquinonesA naphthoquinone in which the oxo groups of the quinone moiety are at positions 1 and 4 of the parent naphthalene 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]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1592253Inhibition of Schistosoma mansoni DHODH assessed as remaining enzyme activity at 250 uM using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay relative to control2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID1397259Selectivity index, ratio of IC50 for human WI38 cells to IC50 for HL60 cells2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Anti-acute myeloid leukemia activity of 2-chloro-3-alkyl-1,4-naphthoquinone derivatives through inducing mtDNA damage and GSH depletion.
AID660269Cytotoxicity against mouse embryo HMC after 24 hrs by Alamar blue assay2012European journal of medicinal chemistry, Jun, Volume: 52On the search for potential anti-Trypanosoma cruzi drugs: synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions.
AID660266Trypanocidal activity against bloodstream form of Trypanosoma cruzi Y isolated from albino mouse blood after 24 hrs by neubauer chamber analysis2012European journal of medicinal chemistry, Jun, Volume: 52On the search for potential anti-Trypanosoma cruzi drugs: synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions.
AID19838Partition coefficient (logP)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID19426HPLC capacity factor (logK)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID19832Partition coefficient (logP)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1397256Cytotoxicity against human HL60 cells after 24 hrs by MTT assay2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Anti-acute myeloid leukemia activity of 2-chloro-3-alkyl-1,4-naphthoquinone derivatives through inducing mtDNA damage and GSH depletion.
AID1397257Cytotoxicity against human HL60 cells after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Anti-acute myeloid leukemia activity of 2-chloro-3-alkyl-1,4-naphthoquinone derivatives through inducing mtDNA damage and GSH depletion.
AID660270Selectivity index, ratio of LC50 for mouse embryo HMC to IC50 for bloodstream form of Trypanosoma cruzi Y2012European journal of medicinal chemistry, Jun, Volume: 52On the search for potential anti-Trypanosoma cruzi drugs: synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions.
AID1397258Cytotoxicity against human WI38 cells after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Anti-acute myeloid leukemia activity of 2-chloro-3-alkyl-1,4-naphthoquinone derivatives through inducing mtDNA damage and GSH depletion.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)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: 28.15

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.15 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index24.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.15)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbazilquinone
Carbazilquinone: An alkylating agent structurally similar to MITOMYCIN and found to be effective in the treatment of leukemia and various other neoplasms in mice. It causes leukemia and thrombocytopenia in almost all human patients.		1.9910organic molecular entity
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.1710nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
lapachol
lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.		2.5220
beta-lapachone
beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.		2.0710benzochromenone;
orthoquinones		anti-inflammatory agent;
antineoplastic agent;
plant 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.		2.44201,4-naphthoquinones;
vitamin K		angiogenesis inhibitor;
antineoplastic agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
human urinary metabolite;
nutraceutical
quinone
benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).		2.44201,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
phenindione
Phenindione: An indandione that has been used as an anticoagulant. Phenindione has actions similar to WARFARIN, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)		1.9610aromatic ketone;
beta-diketone		anticoagulant
triaziquone
Triaziquone: Alkylating antineoplastic agent used mainly for ovarian tumors. It is toxic to skin, gastrointestinal tract, bone marrow and kidneys.. triaziquone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which three of the ring hydrogens are replaced by aziridin-1-yl groups.		1.99101,4-benzoquinones;
aziridines		alkylating agent;
antineoplastic agent
lawsone
lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.		2.5220
dichlone
dichlone: structure		2.0710
1,4-naphthoquinone
naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.		1.99101,4-naphthoquinones
2,5-dimethyl-4-benzoquinone
[no description available]		1.9910
plumbagin
plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.		2.1710hydroxy-1,4-naphthoquinone;
phenols		anticoagulant;
antineoplastic agent;
immunological adjuvant;
metabolite
gentian violet
Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.		2.0710organic chloride saltanthelminthic drug;
antibacterial agent;
antifungal agent;
antiseptic drug;
histological dye
2-methyl-1,4-benzoquinone
cresoquinone: no further information available 6/2003		2.4420
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.		1.9610dichlorobenzene;
quinone imine
2,5-di-tert-butylbenzoquinone
[no description available]		2.2110benzoquinones;
p-quinones
2-amino-3-chloro-1,4-naphthoquinone
2-amino-3-chloro-1,4-naphthoquinone: has antineoplastic activity; structure in first source		1.99101,4-naphthoquinones
2-tert-butyl-4-quinone
2-tert-butyl-4-quinone: a metabolite of butylated hydroxyanisole ; structure given in first source		2.2110
benzonidazole
benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.		2.0710C-nitro compound;
imidazoles;
monocarboxylic acid amide		antiprotozoal drug
diaziquone
diaziquone: RN given refers to parent cpd. diaziquone : A 1,4-benzoquinone that is substituted at positions 2 and 5 have been replaced by aziridin-1-yl groups and at positions 3 and 6 by (ethoxycarbonyl)amino groups.		1.99101,4-benzoquinones;
aziridines;
carbamate ester;
enamine		alkylating agent;
antineoplastic agent
brequinar
brequinar : A quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties.		2.2110biphenyls;
monocarboxylic acid;
monofluorobenzenes;
quinolinemonocarboxylic acid		anticoronaviral agent;
antimetabolite;
antineoplastic agent;
antiviral agent;
EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor;
immunosuppressive agent;
pyrimidine synthesis inhibitor
duroquinone
tetramethyl-1,4-benzoquinone: structure in first source. duroquinone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which all four hydrogens are substituted by methyl groups.		1.99101,4-benzoquinones
2,6-dimethyl-1,4-benzoquinone
[no description available]		1.9910
alpha-lapachone
alpha-lapachone: structure in first source		2.2110organic heterotricyclic compound;
organooxygen compound
2-bromo-1,4-naphthoquinone
2-bromo-1,4-naphthoquinone: structure in first source		2.4220
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.		2.2110hydroxy-1,2-naphthoquinone
hydrolapachol
hydrolapachol: inhibits mitochondrial respiratory chain		2.2110
nsc 30705
NSC 30705: RN given refers to parent cpd; structure given in first source		1.9910
ethylenimine quinone
2,5-bis(aziridin-1-yl)-1,4-benzoquinone : A member of the class of 1,4-benzoquinones that is p-benzoquinone in which the hydrogens at positions 2 and 5 are replaced by aziridin-1-yl groups.		1.99101,4-benzoquinones;
aziridines		alkylating agent;
mutagen
nsc 224070
NSC 224070: structure given in first source. 2,5-bis(2-hydroxyethylamino)-3,6-diaziridinylbenzoquinone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which the hydrogens at positions 2 and 5 have been replaced by aziridin-1-yl groups while the hydrogens at positions 3 and 6 have been replaced by (2-hydroxyethyl)amino groups.		1.99101,4-benzoquinones;
aziridines;
enamine;
primary alcohol;
secondary amino compound		alkylating agent;
antineoplastic agent
2-methylamino-1,4-naphthoquinone
2-methylamino-1,4-naphthoquinone: structure in first source		1.9910
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		1.9610
nor-beta-lapachone
nor-beta-lapachone: has antineoplastic activity; structure in first source		2.0710
vitamin k 1
Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.		1.9610phylloquinones;
vitamin K		cofactor;
human metabolite;
plant metabolite
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		1.9610benzenes;
hydroxycoumarin;
methyl ketone
teriflunomide
[no description available]		2.2110(trifluoromethyl)benzenes;
aromatic amide;
enamide;
enol;
nitrile;
secondary carboxamide		drug metabolite;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
hepatotoxic agent;
non-steroidal anti-inflammatory drug;
tyrosine kinase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		01.9910
B16 Melanoma
[description not available]		01.9910
Acute Myelogenous Leukemia
[description not available]		02.1710
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		02.1710
Schistosoma mansoni Infection
[description not available]		02.2110
Schistosomiasis mansoni
Schistosomiasis caused by Schistosoma mansoni. It is endemic in Africa, the Middle East, South America, and the Caribbean and affects mainly the bowel, spleen, and liver.		02.2110
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