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475-38-7,MFCD00001685
Catalog No.:AA003M88

475-38-7 | 5,8-Dihydroxynaphthalene-1,4-dione

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100mg
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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA003M88
Chemical Name:
5,8-Dihydroxynaphthalene-1,4-dione
CAS Number:
475-38-7
Molecular Formula:
C10H6O4
Molecular Weight:
190.1522
MDL Number:
MFCD00001685
SMILES:
O=C1C=CC(=O)c2c1c(O)ccc2O
Properties
Properties
 
BP:
285.64°C (rough estimate)  
Form:
Solid  
MP:
220-230 °C(lit.)  
Refractive Index:
1.5280 (estimate)  
Storage:
Room Temperature;Keep in dry area;  

Computed Properties
 
Complexity:
277  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
XLogP3:
1.8  

Literature

Title: Covalent binding of quinones activates the Ah receptor in Hepa1c1c7 cells.

Journal: The Journal of toxicological sciences 20151201

Title: Evidence for synergism between cell death mechanisms in a cellular model of neurodegeneration in Parkinson's disease.

Journal: Neurotoxicity research 20121101

Title: Naphthazarin has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model.

Journal: Journal of neuroscience research 20120901

Title: Free radical scavenging activities of naturally occurring and synthetic analogues of sea urchin naphthazarin pigments.

Journal: Natural product communications 20120701

Title: Novel anti-cancer role of naphthazarin in human gastric cancer cells.

Journal: International journal of oncology 20120101

Title: The microtubule depolymerizing agent naphthazarin induces both apoptosis and autophagy in A549 lung cancer cells.

Journal: Apoptosis : an international journal on programmed cell death 20110901

Title: Ligand binding to distinct states diverts aggregation of an amyloid-forming protein.

Journal: Nature chemical biology 20110828

Title: Extension of lifespan in C. elegans by naphthoquinones that act through stress hormesis mechanisms.

Journal: PloS one 20110101

Title: Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases.

Journal: Bioorganic & medicinal chemistry 20090315

Title: Reduction of hydrophilic ubiquinones by the flavin in mitochondrial NADH:ubiquinone oxidoreductase (Complex I) and production of reactive oxygen species.

Journal: Biochemistry 20090310

Title: An efficient formal synthesis of the human telomerase inhibitor (+/-)-gamma-rubromycin.

Journal: Angewandte Chemie (International ed. in English) 20090101

Title: Valence-state analysis through spectroelectrochemistry in a series of quinonoid-bridged diruthenium complexes [(acac)(2)Ru(mu-L)Ru(acac)(2)](n) (n=+2, +1, 0, -1, -2).

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

Title: Thioredoxin glutathione reductase from Schistosoma mansoni: an essential parasite enzyme and a key drug target.

Journal: PLoS medicine 20070601

Title: Determination of naphthazarin derivatives in endemic Turkish Alkanna species by reversed phase high performance liquid chromatography.

Journal: Planta medica 20070301

Title: Effect of colloidal silver against the cytotoxicity of hydrogen peroxide and naphthazarin on primary cultured cortical astrocytes.

Journal: The International journal of neuroscience 20070301

Title: Cytotoxicity in vitro of naphthazarin derivatives from Onosma arenaria.

Journal: Phytotherapy research : PTR 20060701

Title: Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori.

Journal: Journal of ethnopharmacology 20060421

Title: Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins.

Journal: The Journal of organic chemistry 20060203

Title: Naphthazarin and methylnaphthazarin cause vascular dysfunction by impairment of endothelium-derived nitric oxide and increased superoxide anion generation.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20060201

Title: Synthesis and evaluation of antitumor activity of novel 1,4-naphthoquinone derivatives (IV).

Journal: Archives of pharmacal research 20060201

Title: Role of lysosomal cathepsins in naphthazarin- and Fas-induced apoptosis in oral squamous cell carcinoma cells.

Journal: Acta oto-laryngologica 20060101

Title: Synthesis of 5-nitro-2-furancarbohydrazides and their cis-diamminedichloroplatinum complexes as bitopic and irreversible human thioredoxin reductase inhibitors.

Journal: Journal of medicinal chemistry 20051103

Title: Synthesis of (1,4)-naphthoquinono-[3,2-c]-1H-pyrazoles and their (1,4)-naphthohydroquinone derivatives as antifungal, antibacterial, and anticancer agents.

Journal: Bioorganic & medicinal chemistry letters 20050701

Title: Ab initio and semiempirical study of structure and electronic spectra of hydroxy substituted naphthoquinones.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050201

Title: Effects of redox cycling compounds on DT diaphorase activity in the liver of rainbow trout (Oncorhynchus mykiss).

Journal: Comparative hepatology 20050101

Title: Alkaline-earth cations enhance ortho-quinone-catalyzed ascorbate oxidation.

Journal: Free radical biology & medicine 20041115

Title: Use of 1,4-naphthoquinones for control of Erwinia carotovora.

Journal: Canadian journal of microbiology 20041101

Title: Quinones as antimycobacterial agents.

Journal: Bioorganic & medicinal chemistry 20040915

Title: Synthesis and cytotoxicity study of alkannin derivatives.

Journal: European journal of medicinal chemistry 20040901

Title: Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents.

Journal: Bioorganic & medicinal chemistry letters 20040308

Title: Fourier transform infrared and Raman spectra, vibrational assignment and density functional theory calculations of naphthazarin.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20040101

Title: Inhibitory effect of a naphthazarin derivative, S64, on heat shock factor (Hsf) activation and glutathione status following hypoxia.

Journal: Cell biology and toxicology 20031001

Title: Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation.

Journal: Phytotherapy research : PTR 20030501

Title: United States Department of Agriculture-Agricultural Research Service studies on polyketide toxins of Fusarium oxysporum f sp vasinfectum: potential targets for disease control.

Journal: Pest management science 20030101

Title: Protective effects of rilmenidine and AGN 192403 on oxidative cytotoxicity and mitochondrial inhibitor-induced cytotoxicity in astrocytes.

Journal: Free radical biology & medicine 20021115

Title: Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20021101

Title: In vitro antimicrobial activity of a new series of 1,4-naphthoquinones.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20020701

Title: Alkannin and shikonin: effect on free radical processes and on inflammation - a preliminary pharmacochemical investigation.

Journal: Archiv der Pharmazie 20020601

Title: [Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20020401

Title: Imidazoline drugs stabilize lysosomes and inhibit oxidative cytotoxicity in astrocytes.

Journal: Free radical biology & medicine 20020301

Title: Synthesis of cis- and trans-5,8-dihydroxy-5,6,7,8-tetrahydro-1,4-naphthoquinone.

Journal: Chemical & pharmaceutical bulletin 20011001

Title: Specific inhibition of human immunodeficiency virus type 1 (HIV-1) integration in cell culture: putative inhibitors of HIV-1 integrase.

Journal: Antimicrobial agents and chemotherapy 20010901

Title: Bromination studies of the 2,3-dimethylnaphthazarin core allowing easy access to naphthazarin derivatives.

Journal: The Journal of organic chemistry 20010810

Title: Naphthazarin derivatives (VII): antitumor action against ICR mice bearing ascitic S-180 cells.

Journal: Archives of pharmacal research 20010601

Title: Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases.

Journal: Biological & pharmaceutical bulletin 20010301

Title: Relocalization of cathepsin D and cytochrome c early in apoptosis revealed by immunoelectron microscopy.

Journal: Laboratory investigation; a journal of technical methods and pathology 20010201

Title: Naphthazarin derivatives (VII): antitumor action against ICR mice bearing ascitic S-180 cells.

Journal: Archives of pharmacal research 20010201

Title: Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid.

Journal: Chemico-biological interactions 20000103

Title: Discovery and analysis of inhibitors of the human immunodeficiency integrase.

Journal: Drug design and discovery 19970501

Title: Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19960903

Title: Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.

Journal: Biochimica et biophysica acta 19951115

Title: Inhibitors of human immunodeficiency virus integrase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930315

Title: Seon Young Choi, et al. Naphthazarin has a protective effect on the 1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine-induced Parkinson's disease model. J Neurosci Res. 2012 Sep;90(9):1842-9.

Title: Omar Aljanadi, et al. Stimulation of Suicidal Erythrocyte Death by Naphthazarin. Basic Clin Pharmacol Toxicol. 2015 Dec;117(6):369-74.

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Tags:475-38-7 Molecular Formula|475-38-7 MDL|475-38-7 SMILES|475-38-7 5,8-Dihydroxynaphthalene-1,4-dione