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4707-32-8

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

CAS No: 4707-32-8 Catalog No: AG0038Q6 MDL No:MFCD01712233

Product Description

Catalog Number:
AG0038Q6
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
IUPAC Name:
2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
InChI:
InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
InChI Key:
QZPQTZZNNJUOLS-UHFFFAOYSA-N
SMILES:
O=C1C2=C(OC(CC2)(C)C)c2c(C1=O)cccc2
UNII:
6N4FA2QQ6A

Properties

Complexity:
445  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
242.094g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
242.274g/mol
Monoisotopic Mass:
242.094g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
43.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2  

Literature

Title Journal
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Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
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 of medicinal chemistry 20120823
New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms. Bioorganic & medicinal chemistry 20120815
β-Lapachone analogs with enhanced antiproliferative activity. European journal of medicinal chemistry 20120701
An NQO1 substrate with potent antitumor activity that selectively kills by PARP1-induced programmed necrosis. Cancer research 20120615
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. European journal of medicinal chemistry 20120601
Screening of anti-cancer agent using zebrafish: comparison with the MTT assay. Biochemical and biophysical research communications 20120525
NAD(P)H:quinone oxidoreductase 1 (NQO1) in the sensitivity and resistance to antitumor quinones. Biochemical pharmacology 20120415
Prevention of salt-induced renal injury by activation of NAD(P)H:quinone oxidoreductase 1, associated with NADPH oxidase. Free radical biology & medicine 20120301
Temperature-sensitive gels for intratumoral delivery of β-lapachone: effect of cyclodextrins and ethanol. TheScientificWorldJournal 20120101
No role of homologous recombination in dealing with β-lapachone cytotoxicity in yeast. Chemical research in toxicology 20111219
Preclinical genotoxicology of nor-β-lapachone in human cultured lymphocytes and Chinese hamster lung fibroblasts. Chemical research in toxicology 20110919
Corpus cavernosal smooth muscle relaxation effect of a novel AMPK activator, beta-lapachone. The journal of sexual medicine 20110801
Activation of NAD(P)H:quinone oxidoreductase ameliorates spontaneous hypertension in an animal model via modulation of eNOS activity. Cardiovascular research 20110801
Synthesis and anti-Trypanosoma cruzi activity of β-lapachone analogues. European journal of medicinal chemistry 20110701
β-lapachone accelerates the recovery of burn-wound skin. Histology and histopathology 20110701
Identification of nor-β-lapachone derivatives as potential antibacterial compounds against Enterococcus faecalis clinical strain. Current microbiology 20110201
β-Lapachone-induced reactive oxygen species (ROS) generation mediates autophagic cell death in glioma U87 MG cells. Chemico-biological interactions 20110115
Modulating endogenous NQO1 levels identifies key regulatory mechanisms of action of β-lapachone for pancreatic cancer therapy. Clinical cancer research : an official journal of the American Association for Cancer Research 20110115
Trypanosoma cruzi: insights into naphthoquinone effects on growth and proteinase activity. Experimental parasitology 20110101
Hyperthermia enhances the effect of β-lapachone to cause γH2AX formations and cell death in human osteosarcoma cells. International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20110101
Synthesis and evaluation of quinonoid compounds against tumor cell lines. European journal of medicinal chemistry 20110101
Synthesis of biologically active (-)-dehydroiso-β-lapachone and the determination of its absolute configuration. Chemical & pharmaceutical bulletin 20110101
Endoplasmic reticulum stress-induced JNK activation is a critical event leading to mitochondria-mediated cell death caused by β-lapachone treatment. PloS one 20110101
β-Lapachone induces heart morphogenetic and functional defects by promoting the death of erythrocytes and the endocardium in zebrafish embryos. Journal of biomedical science 20110101
β-lapachone significantly increases the effect of ionizing radiation to cause mitochondrial apoptosis via JNK activation in cancer cells. PloS one 20110101
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
Prostate cancer radiosensitization through poly(ADP-Ribose) polymerase-1 hyperactivation. Cancer research 20101015
Activity of β-lapachone derivatives against rifampicin-susceptible and -resistant strains of Mycobacterium tuberculosis. Tuberculosis (Edinburgh, Scotland) 20100901
Synthesis of naturally occurring naphthoquinone epoxides and application in the synthesis of beta-lapachone. Organic & biomolecular chemistry 20100821
Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB. Experimental & molecular medicine 20100531
Beta-lapachone micellar nanotherapeutics for non-small cell lung cancer therapy. Cancer research 20100515
A naphthoquinone derivative can induce anemia through phosphatidylserine exposure-mediated erythrophagocytosis. The Journal of pharmacology and experimental therapeutics 20100501
The evaluation of quinonoid compounds against Trypanosoma cruzi: synthesis of imidazolic anthraquinones, nor-beta-lapachone derivatives and beta-lapachone-based 1,2,3-triazoles. Bioorganic & medicinal chemistry 20100501
Antifungal activity of the naphthoquinone beta-lapachone against disseminated infection with Cryptococcus neoformans var. neoformans in dexamethasone-immunosuppressed Swiss mice. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20100401
Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol. Bioorganic & medicinal chemistry 20100401
Paclitaxel and beta-lapachone synergistically induce apoptosis in human retinoblastoma Y79 cells by downregulating the levels of phospho-Akt. Journal of cellular physiology 20100201
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors. Bioorganic & medicinal chemistry letters 20091201
The trypanocidal activity of naphthoquinones: a review. Molecules (Basel, Switzerland) 20091110
Cisplatin enhances the anticancer effect of beta-lapachone by upregulating NQO1. Anti-cancer drugs 20091101
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Nature chemical biology 20091001
Toxicological assessment of beta-lapachone on organs from pregnant and non-pregnant rats. Phytotherapy research : PTR 20090901
Synthesis and evaluation of bioactive naphthoquinones from the Brazilian medicinal plant, Tabebuia avellanedae. Bioorganic & medicinal chemistry 20090901
In vitro synergic effect of beta-lapachone and isoniazid on the growth of Mycobacterium fortuitum and Mycobacterium smegmatis. Memorias do Instituto Oswaldo Cruz 20090701
Activation of NAD(P)H:quinone oxidoreductase 1 prevents arterial restenosis by suppressing vascular smooth muscle cell proliferation. Circulation research 20090410
Restenosis revisited. Circulation research 20090410
Pharmacological stimulation of NADH oxidation ameliorates obesity and related phenotypes in mice. Diabetes 20090401
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. Chembiochem : a European journal of chemical biology 20090213
Photosensitizing properties of triplet beta-lapachones in acetonitrile solution. Photochemistry and photobiology 20090101
In vitro metabolism of beta-lapachone (ARQ 501) in mammalian hepatocytes and cultured human cells. Rapid communications in mass spectrometry : RCM 20090101
Increased susceptibility of spinal muscular atrophy fibroblasts to camptothecin is p53-independent. BMC cell biology 20090101
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. International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20090101
Modulatory effects of Tabebuia impetiginosa (Lamiales, Bignoniaceae) on doxorubicin-induced somatic mutation and recombination in Drosophila melanogaster. Genetics and molecular biology 20090101
Involvement of endoplasmic reticulum stress and activation of MAP kinases in beta-lapachone-induced human prostate cancer cell apoptosis. Histology and histopathology 20081101
Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol. Bioorganic & medicinal chemistry letters 20081015
Inner reorganization during the radical-biradical transition in a nor-beta-lapachone derivative possessing two redox centers. Organic & biomolecular chemistry 20080921
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 of chromatography. B, Analytical technologies in the biomedical and life sciences 20080901
Inactivation of the SMN complex by oxidative stress. Molecular cell 20080725
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. Drug metabolism and disposition: the biological fate of chemicals 20080401
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. Drug metabolism and disposition: the biological fate of chemicals 20080401
Laser flash photolysis study of the triplet reactivity of beta-lapachones. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080401
Beta-lapachone inhibits proliferation and induces apoptosis in retinoblastoma cell lines. Eye (London, England) 20080301
Anti-cancer effect of bio-reductive drug beta-lapachon is enhanced by activating NQO1 with heat shock. International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20080301
Topoisomerase inhibitors as anti-arthritic agents. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20080301
Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms. Bioorganic & medicinal chemistry 20080115
Compatibility of the antitumoral beta-lapachone with different solid dosage forms excipients. Journal of pharmaceutical and biomedical analysis 20071130
Beta-lapachone-containing PEG-PLA polymer micelles as novel nanotherapeutics against NQO1-overexpressing tumor cells. Journal of controlled release : official journal of the Controlled Release Society 20071008
Induction of Egr-1 is associated with anti-metastatic and anti-invasive ability of beta-lapachone in human hepatocarcinoma cells. Bioscience, biotechnology, and biochemistry 20070901
Upregulation of NAD(P)H:quinone oxidoreductase by radiation potentiates the effect of bioreductive beta-lapachone on cancer cells. Neoplasia (New York, N.Y.) 20070801
Nonhomologous end joining is essential for cellular resistance to the novel antitumor agent, beta-lapachone. Cancer research 20070715
Applications of counter-current chromatography in organic synthesis purification of heterocyclic derivatives of lapachol. Journal of chromatography. A 20070601
Involvement of NO/cGMP signaling in the apoptotic and anti-angiogenic effects of beta-lapachone on endothelial cells in vitro. Journal of cellular physiology 20070501
Anti-inflammatory effects of beta-lapachone in lipopolysaccharide-stimulated BV2 microglia. International immunopharmacology 20070401
Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line. Journal of medicinal chemistry 20070222
Calcium-dependent modulation of poly(ADP-ribose) polymerase-1 alters cellular metabolism and DNA repair. The Journal of biological chemistry 20061103
Beta-lapachone activates a Mre11p-Tel1p G1/S checkpoint in budding yeast. Cell cycle (Georgetown, Tex.) 20061101
Modulating beta-lapachone release from polymer millirods through cyclodextrin complexation. Journal of pharmaceutical sciences 20061001
Oxyrane derivative of alpha-lapachone is potent growth inhibitor of Trypanosoma cruzi epimastigote forms. Parasitology research 20060901
Synergistic effects of radiation and beta-lapachone in DU-145 human prostate cancer cells in vitro. Radiation research 20060501
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. Magnetic resonance in chemistry : MRC 20060401
beta-lapachone induces growth inhibition and apoptosis in bladder cancer cells by modulation of Bcl-2 family and activation of caspases. Experimental oncology 20060301
Beta-lapachone, a quinone isolated from Tabebuia avellanedae, induces apoptosis in HepG2 hepatoma cell line through induction of Bax and activation of caspase. Journal of medicinal food 20060101
Heat-induced up-regulation of NAD(P)H:quinone oxidoreductase potentiates anticancer effects of beta-lapachone. Clinical cancer research : an official journal of the American Association for Cancer Research 20051215
Effect of a beta-lapachone-derived naphthoimidazole on Trypanosoma cruzi: identification of target organelles. The Journal of antimicrobial chemotherapy 20051201
Development of beta-lapachone prodrugs for therapy against human cancer cells with elevated NAD(P)H:quinone oxidoreductase 1 levels. Clinical cancer research : an official journal of the American Association for Cancer Research 20050415
Growth inhibition of A549 human lung carcinoma cells by beta-lapachone through induction of apoptosis and inhibition of telomerase activity. International journal of oncology 20050401
Antiplasmodial activity of naphthoquinones related to lapachol and beta-lapachone. Chemistry & biodiversity 20050201
Susceptibility of cancer cells to beta-lapachone is enhanced by ionizing radiation. International journal of radiation oncology, biology, physics 20050101
Efficacy of beta-lapachone in pancreatic cancer treatment: exploiting the novel, therapeutic target NQO1. Cancer biology & therapy 20050101
2-Phenyl-beta-lapachone can affect mitochondrial function by redox cycling mediated oxidation. Archives of biochemistry and biophysics 20041215
Alkaline-earth cations enhance ortho-quinone-catalyzed ascorbate oxidation. Free radical biology & medicine 20041115
Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor kappaB inhibition. Biochemical pharmacology 20040915
Studies on the trypanocidal activity of semi-synthetic pyran[b-4,3]naphtho[1,2-d]imidazoles from beta-lapachone. European journal of medicinal chemistry 20040701
Cyr61 expression confers resistance to apoptosis in breast cancer MCF-7 cells by a mechanism of NF-kappaB-dependent XIAP up-regulation. The Journal of biological chemistry 20040604
Antimalarial activity of phenazines from lapachol, beta-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Bioorganic & medicinal chemistry letters 20040308
beta-Lapachone-induced apoptosis is associated with activation of caspase-3 and inactivation of NF-kappaB in human colon cancer HCT-116 cells. Anti-cancer drugs 20031101
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beta-Lapachone reduces endotoxin-induced macrophage activation and lung edema and mortality. American journal of respiratory and critical care medicine 20030701
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beta-lapachone, a novel plant product, overcomes drug resistance in human multiple myeloma cells. Experimental hematology 20020701
Reduction of lapachones and their reaction with L-cysteine and mercaptoethanol on glassy carbon electrodes. Bioelectrochemistry (Amsterdam, Netherlands) 20020515
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Chemosensitivity of human prostate cancer cells PC3 and LNCaP to genistein isoflavone and beta-lapachone. Biology of the cell 20020201
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beta-Lapachone-induced apoptosis in human prostate cancer cells: involvement of NQO1/xip3. Experimental cell research 20010701
Characterization of poly(ADP-ribose)polymerase from Crithidia fasciculata: enzyme inhibition by beta-lapachone. Molecular and biochemical parasitology 20010701
Calcium is a key signaling molecule in beta-lapachone-mediated cell death. The Journal of biological chemistry 20010601
Induction of CDK inhibitors (p21(WAF1) and p27(Kip1)) and Bak in the beta-lapachone-induced apoptosis of human prostate cancer cells. Molecular pharmacology 20010401
Effect of dyskinetoplastic agents on ultrastructure and oxidative phosphorylation in Crithidia fasciculata. Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al 20010401
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