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4707-32-8,MFCD01712233
Catalog No.:AA0038NE

4707-32-8 | 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione

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50mg
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100mg
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0038NE
Chemical Name:
3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione
CAS Number:
4707-32-8
Molecular Formula:
C15H14O3
Molecular Weight:
242.2699
MDL Number:
MFCD01712233
SMILES:
O=C1C2=C(OC(CC2)(C)C)c2c(C1=O)cccc2
Properties
Computed Properties
 
Complexity:
445  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
3  
XLogP3:
2.2  

Literature

Title: Human NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated inactivation of reactive quinoneimine metabolites of diclofenac and mefenamic acid.

Journal: Chemical research in toxicology 20140421

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide.

Journal: Journal of medicinal chemistry 20120823

Title: New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms.

Journal: Bioorganic & medicinal chemistry 20120815

Title: β-Lapachone analogs with enhanced antiproliferative activity.

Journal: European journal of medicinal chemistry 20120701

Title: An NQO1 substrate with potent antitumor activity that selectively kills by PARP1-induced programmed necrosis.

Journal: Cancer research 20120615

Title: On 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.

Journal: European journal of medicinal chemistry 20120601

Title: Screening of anti-cancer agent using zebrafish: comparison with the MTT assay.

Journal: Biochemical and biophysical research communications 20120525

Title: NAD(P)H:quinone oxidoreductase 1 (NQO1) in the sensitivity and resistance to antitumor quinones.

Journal: Biochemical pharmacology 20120415

Title: Prevention of salt-induced renal injury by activation of NAD(P)H:quinone oxidoreductase 1, associated with NADPH oxidase.

Journal: Free radical biology & medicine 20120301

Title: Temperature-sensitive gels for intratumoral delivery of β-lapachone: effect of cyclodextrins and ethanol.

Journal: TheScientificWorldJournal 20120101

Title: No role of homologous recombination in dealing with β-lapachone cytotoxicity in yeast.

Journal: Chemical research in toxicology 20111219

Title: Preclinical genotoxicology of nor-β-lapachone in human cultured lymphocytes and Chinese hamster lung fibroblasts.

Journal: Chemical research in toxicology 20110919

Title: Corpus cavernosal smooth muscle relaxation effect of a novel AMPK activator, beta-lapachone.

Journal: The journal of sexual medicine 20110801

Title: Activation of NAD(P)H:quinone oxidoreductase ameliorates spontaneous hypertension in an animal model via modulation of eNOS activity.

Journal: Cardiovascular research 20110801

Title: Synthesis and anti-Trypanosoma cruzi activity of β-lapachone analogues.

Journal: European journal of medicinal chemistry 20110701

Title: β-lapachone accelerates the recovery of burn-wound skin.

Journal: Histology and histopathology 20110701

Title: Identification of nor-β-lapachone derivatives as potential antibacterial compounds against Enterococcus faecalis clinical strain.

Journal: Current microbiology 20110201

Title: β-Lapachone-induced reactive oxygen species (ROS) generation mediates autophagic cell death in glioma U87 MG cells.

Journal: Chemico-biological interactions 20110115

Title: Modulating endogenous NQO1 levels identifies key regulatory mechanisms of action of β-lapachone for pancreatic cancer therapy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110115

Title: Trypanosoma cruzi: insights into naphthoquinone effects on growth and proteinase activity.

Journal: Experimental parasitology 20110101

Title: Hyperthermia enhances the effect of β-lapachone to cause γH2AX formations and cell death in human osteosarcoma cells.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20110101

Title: Synthesis and evaluation of quinonoid compounds against tumor cell lines.

Journal: European journal of medicinal chemistry 20110101

Title: Synthesis of biologically active (-)-dehydroiso-β-lapachone and the determination of its absolute configuration.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Endoplasmic reticulum stress-induced JNK activation is a critical event leading to mitochondria-mediated cell death caused by β-lapachone treatment.

Journal: PloS one 20110101

Title: β-Lapachone induces heart morphogenetic and functional defects by promoting the death of erythrocytes and the endocardium in zebrafish embryos.

Journal: Journal of biomedical science 20110101

Title: β-lapachone significantly increases the effect of ionizing radiation to cause mitochondrial apoptosis via JNK activation in cancer cells.

Journal: PloS one 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Prostate cancer radiosensitization through poly(ADP-Ribose) polymerase-1 hyperactivation.

Journal: Cancer research 20101015

Title: Activity of β-lapachone derivatives against rifampicin-susceptible and -resistant strains of Mycobacterium tuberculosis.

Journal: Tuberculosis (Edinburgh, Scotland) 20100901

Title: Synthesis of naturally occurring naphthoquinone epoxides and application in the synthesis of beta-lapachone.

Journal: Organic & biomolecular chemistry 20100821

Title: Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB.

Journal: Experimental & molecular medicine 20100531

Title: Beta-lapachone micellar nanotherapeutics for non-small cell lung cancer therapy.

Journal: Cancer research 20100515

Title: A naphthoquinone derivative can induce anemia through phosphatidylserine exposure-mediated erythrophagocytosis.

Journal: The Journal of pharmacology and experimental therapeutics 20100501

Title: The evaluation of quinonoid compounds against Trypanosoma cruzi: synthesis of imidazolic anthraquinones, nor-beta-lapachone derivatives and beta-lapachone-based 1,2,3-triazoles.

Journal: Bioorganic & medicinal chemistry 20100501

Title: Antifungal activity of the naphthoquinone beta-lapachone against disseminated infection with Cryptococcus neoformans var. neoformans in dexamethasone-immunosuppressed Swiss mice.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20100401

Title: Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol.

Journal: Bioorganic & medicinal chemistry 20100401

Title: Paclitaxel and beta-lapachone synergistically induce apoptosis in human retinoblastoma Y79 cells by downregulating the levels of phospho-Akt.

Journal: Journal of cellular physiology 20100201

Title: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: The trypanocidal activity of naphthoquinones: a review.

Journal: Molecules (Basel, Switzerland) 20091110

Title: Cisplatin enhances the anticancer effect of beta-lapachone by upregulating NQO1.

Journal: Anti-cancer drugs 20091101

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Toxicological assessment of beta-lapachone on organs from pregnant and non-pregnant rats.

Journal: Phytotherapy research : PTR 20090901

Title: Synthesis and evaluation of bioactive naphthoquinones from the Brazilian medicinal plant, Tabebuia avellanedae.

Journal: Bioorganic & medicinal chemistry 20090901

Title: In vitro synergic effect of beta-lapachone and isoniazid on the growth of Mycobacterium fortuitum and Mycobacterium smegmatis.

Journal: Memorias do Instituto Oswaldo Cruz 20090701

Title: Activation of NAD(P)H:quinone oxidoreductase 1 prevents arterial restenosis by suppressing vascular smooth muscle cell proliferation.

Journal: Circulation research 20090410

Title: Restenosis revisited.

Journal: Circulation research 20090410

Title: Pharmacological stimulation of NADH oxidation ameliorates obesity and related phenotypes in mice.

Journal: Diabetes 20090401

Title: Ex vivo activities of beta-lapachone and alpha-lapachone on macrophages: a quantitative pharmacological analysis based on amperometric monitoring of oxidative bursts by single cells.

Journal: Chembiochem : a European journal of chemical biology 20090213

Title: Photosensitizing properties of triplet beta-lapachones in acetonitrile solution.

Journal: Photochemistry and photobiology 20090101

Title: In vitro metabolism of beta-lapachone (ARQ 501) in mammalian hepatocytes and cultured human cells.

Journal: Rapid communications in mass spectrometry : RCM 20090101

Title: Increased susceptibility of spinal muscular atrophy fibroblasts to camptothecin is p53-independent.

Journal: BMC cell biology 20090101

Title: Heat shock increases expression of NAD(P)H:quinone oxidoreductase (NQO1), mediator of beta-lapachone cytotoxicity, by increasing NQO1 gene activity and via Hsp70-mediated stabilisation of NQO1 protein.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20090101

Title: Modulatory effects of Tabebuia impetiginosa (Lamiales, Bignoniaceae) on doxorubicin-induced somatic mutation and recombination in Drosophila melanogaster.

Journal: Genetics and molecular biology 20090101

Title: Involvement of endoplasmic reticulum stress and activation of MAP kinases in beta-lapachone-induced human prostate cancer cell apoptosis.

Journal: Histology and histopathology 20081101

Title: Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.

Journal: Bioorganic & medicinal chemistry letters 20081015

Title: Inner reorganization during the radical-biradical transition in a nor-beta-lapachone derivative possessing two redox centers.

Journal: Organic & biomolecular chemistry 20080921

Title: Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ARQ 501 (beta-lapachone) in plasma and tumors from nu/nu mouse xenografts.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080901

Title: Inactivation of the SMN complex by oxidative stress.

Journal: Molecular cell 20080725

Title: Identification of the in vitro metabolites of 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione (ARQ 501; beta-lapachone) in whole blood.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080401

Title: Identification of a novel glucosylsulfate conjugate as a metabolite of 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione (ARQ 501, beta-lapachone) in mammals.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080401

Title: Laser flash photolysis study of the triplet reactivity of beta-lapachones.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080401

Title: Beta-lapachone inhibits proliferation and induces apoptosis in retinoblastoma cell lines.

Journal: Eye (London, England) 20080301

Title: Anti-cancer effect of bio-reductive drug beta-lapachon is enhanced by activating NQO1 with heat shock.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20080301

Title: Topoisomerase inhibitors as anti-arthritic agents.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20080301

Title: Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms.

Journal: Bioorganic & medicinal chemistry 20080115

Title: Compatibility of the antitumoral beta-lapachone with different solid dosage forms excipients.

Journal: Journal of pharmaceutical and biomedical analysis 20071130

Title: Beta-lapachone-containing PEG-PLA polymer micelles as novel nanotherapeutics against NQO1-overexpressing tumor cells.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20071008

Title: Induction of Egr-1 is associated with anti-metastatic and anti-invasive ability of beta-lapachone in human hepatocarcinoma cells.

Journal: Bioscience, biotechnology, and biochemistry 20070901

Title: Upregulation of NAD(P)H:quinone oxidoreductase by radiation potentiates the effect of bioreductive beta-lapachone on cancer cells.

Journal: Neoplasia (New York, N.Y.) 20070801

Title: Nonhomologous end joining is essential for cellular resistance to the novel antitumor agent, beta-lapachone.

Journal: Cancer research 20070715

Title: Applications of counter-current chromatography in organic synthesis purification of heterocyclic derivatives of lapachol.

Journal: Journal of chromatography. A 20070601

Title: Involvement of NO/cGMP signaling in the apoptotic and anti-angiogenic effects of beta-lapachone on endothelial cells in vitro.

Journal: Journal of cellular physiology 20070501

Title: Anti-inflammatory effects of beta-lapachone in lipopolysaccharide-stimulated BV2 microglia.

Journal: International immunopharmacology 20070401

Title: Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line.

Journal: Journal of medicinal chemistry 20070222

Title: Calcium-dependent modulation of poly(ADP-ribose) polymerase-1 alters cellular metabolism and DNA repair.

Journal: The Journal of biological chemistry 20061103

Title: Beta-lapachone activates a Mre11p-Tel1p G1/S checkpoint in budding yeast.

Journal: Cell cycle (Georgetown, Tex.) 20061101

Title: Modulating beta-lapachone release from polymer millirods through cyclodextrin complexation.

Journal: Journal of pharmaceutical sciences 20061001

Title: Oxyrane derivative of alpha-lapachone is potent growth inhibitor of Trypanosoma cruzi epimastigote forms.

Journal: Parasitology research 20060901

Title: Synergistic effects of radiation and beta-lapachone in DU-145 human prostate cancer cells in vitro.

Journal: Radiation research 20060501

Title: Preparation of alpha-diazocarbonyl compounds from beta-lapachone derivatives and other 1,2-naphthoquinones: use of the 2D NMR 1H,15N and 1H,13C HMBC techniques in assigning regiochemistry.

Journal: Magnetic resonance in chemistry : MRC 20060401

Title: beta-lapachone induces growth inhibition and apoptosis in bladder cancer cells by modulation of Bcl-2 family and activation of caspases.

Journal: Experimental oncology 20060301

Title: Beta-lapachone, a quinone isolated from Tabebuia avellanedae, induces apoptosis in HepG2 hepatoma cell line through induction of Bax and activation of caspase.

Journal: Journal of medicinal food 20060101

Title: Heat-induced up-regulation of NAD(P)H:quinone oxidoreductase potentiates anticancer effects of beta-lapachone.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20051215

Title: Effect of a beta-lapachone-derived naphthoimidazole on Trypanosoma cruzi: identification of target organelles.

Journal: The Journal of antimicrobial chemotherapy 20051201

Title: Development of beta-lapachone prodrugs for therapy against human cancer cells with elevated NAD(P)H:quinone oxidoreductase 1 levels.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050415

Title: Growth inhibition of A549 human lung carcinoma cells by beta-lapachone through induction of apoptosis and inhibition of telomerase activity.

Journal: International journal of oncology 20050401

Title: Antiplasmodial activity of naphthoquinones related to lapachol and beta-lapachone.

Journal: Chemistry & biodiversity 20050201

Title: Susceptibility of cancer cells to beta-lapachone is enhanced by ionizing radiation.

Journal: International journal of radiation oncology, biology, physics 20050101

Title: Efficacy of beta-lapachone in pancreatic cancer treatment: exploiting the novel, therapeutic target NQO1.

Journal: Cancer biology & therapy 20050101

Title: 2-Phenyl-beta-lapachone can affect mitochondrial function by redox cycling mediated oxidation.

Journal: Archives of biochemistry and biophysics 20041215

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

Journal: Free radical biology & medicine 20041115

Title: Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor kappaB inhibition.

Journal: Biochemical pharmacology 20040915

Title: Studies on the trypanocidal activity of semi-synthetic pyran[b-4,3]naphtho[1,2-d]imidazoles from beta-lapachone.

Journal: European journal of medicinal chemistry 20040701

Title: Cyr61 expression confers resistance to apoptosis in breast cancer MCF-7 cells by a mechanism of NF-kappaB-dependent XIAP up-regulation.

Journal: The Journal of biological chemistry 20040604

Title: Antimalarial activity of phenazines from lapachol, beta-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo.

Journal: Bioorganic & medicinal chemistry letters 20040308

Title: beta-Lapachone-induced apoptosis is associated with activation of caspase-3 and inactivation of NF-kappaB in human colon cancer HCT-116 cells.

Journal: Anti-cancer drugs 20031101

Title: Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes.

Journal: Pharmaceutical research 20031001

Title: beta-Lapachone reduces endotoxin-induced macrophage activation and lung edema and mortality.

Journal: American journal of respiratory and critical care medicine 20030701

Title: Inhibitory effects of lapachol derivatives on epstein-barr virus activation.

Journal: Bioorganic & medicinal chemistry 20030220

Title: Mu-calpain activation in beta-lapachone-mediated apoptosis.

Journal: Cancer biology & therapy 20030101

Title: Calpains can do it alone: implications for cancer therapy.

Journal: Cancer biology & therapy 20030101

Title: Toxic potential of dietary genistein isoflavone and beta-lapachone on capacitation and acrosome reaction of epididymal spermatozoa.

Journal: Journal of medicinal food 20030101

Title: Cancer therapy with beta-lapachone.

Journal: Current cancer drug targets 20020901

Title: Studies on fertilization in the teleost IV. Effects of aphidicolin and camptothecin on chromosome formation in fertilized medaka eggs.

Journal: Development, growth & differentiation 20020801

Title: Effect of the lipophilic o-naphthoquinone CG 10-248 on rat liver mitochondria structure and function.

Journal: Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al 20020801

Title: Inhibition of poly(ADP-ribose) polymerase activation attenuates beta-lapachone-induced necrotic cell death in human osteosarcoma cells.

Journal: Toxicology and applied pharmacology 20020715

Title: beta-lapachone, a novel plant product, overcomes drug resistance in human multiple myeloma cells.

Journal: Experimental hematology 20020701

Title: Reduction of lapachones and their reaction with L-cysteine and mercaptoethanol on glassy carbon electrodes.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20020515

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Chemosensitivity of human prostate cancer cells PC3 and LNCaP to genistein isoflavone and beta-lapachone.

Journal: Biology of the cell 20020201

Title: Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of beta-lapachone.

Journal: Journal of medicinal chemistry 20010719

Title: beta-Lapachone-induced apoptosis in human prostate cancer cells: involvement of NQO1/xip3.

Journal: Experimental cell research 20010701

Title: Characterization of poly(ADP-ribose)polymerase from Crithidia fasciculata: enzyme inhibition by beta-lapachone.

Journal: Molecular and biochemical parasitology 20010701

Title: Calcium is a key signaling molecule in beta-lapachone-mediated cell death.

Journal: The Journal of biological chemistry 20010601

Title: Induction of CDK inhibitors (p21(WAF1) and p27(Kip1)) and Bak in the beta-lapachone-induced apoptosis of human prostate cancer cells.

Journal: Molecular pharmacology 20010401

Title: Effect of dyskinetoplastic agents on ultrastructure and oxidative phosphorylation in Crithidia fasciculata.

Journal: Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al 20010401

Title: Novel mechanism of cellular DNA topoisomerase II inhibition by the pyranonaphthoquinone derivatives alpha-lapachone and beta-lapachone.

Journal: Cancer chemotherapy and pharmacology 20010301

Title: p53-independent upregulation of KILLER/DR5 TRAIL receptor expression by glucocorticoids and interferon-gamma.

Journal: Experimental cell research 20010115

Title: [Cytotoxicity of beta-lapachone, an naphthoquinone with possible therapeutic use].

Journal: Medicina 20010101

Title: Comparison of antibacterial and antifungal activities of lapachol and beta-lapachone.

Journal: Planta medica 19940801

Title: Three inhibitors of type 1 human immunodeficiency virus long terminal repeat-directed gene expression and virus replication.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930301

Title: Li CJ, et al. beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J Biol Chem. 1993 Oct 25;268(30):22463-8.

Title: Vanni A, et al. DNA damage and cytotoxicity induced by beta-lapachone: relation to poly(ADP-ribose) polymerase inhibition. Mutat Res. 1998 Jun 5;401(1-2):55-63.

Title: Kim TW, et al. β-Lapachone enhances Mre11-Rad50-Nbs1 complex expression in cisplatin-induced nephrotoxicity. Pharmacol Rep. 2016 Feb;68(1):27-31.

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SDS
Tags:4707-32-8 Molecular Formula|4707-32-8 MDL|4707-32-8 SMILES|4707-32-8 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione