Home Quinolines 10421-76-8
10421-76-8,MFCD00127721
Catalog No.:AA00HA8A

10421-76-8 | 6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3h-isobenzofuran-1-one

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1g
95%
in stock  
$62.00   $44.00
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5g
95%
in stock  
$162.00   $113.00
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10g
95%
in stock  
$261.00   $183.00
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25g
95%
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$477.00   $334.00
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  • Technical Information
  • Properties
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00HA8A
Chemical Name:
6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3h-isobenzofuran-1-one
CAS Number:
10421-76-8
Molecular Formula:
C22H23NO7
Molecular Weight:
413.4205
MDL Number:
MFCD00127721
SMILES:
COc1ccc2c(c1OC)C(=O)OC2C1N(C)CCc2c1c(OC)c1c(c2)OCO1
Properties
Computed Properties
 
Complexity:
647  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
8  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
2  
XLogP3:
2.7  

Literature

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: Metabolic map and bioactivation of the anti-tumour drug noscapine.

Journal: British journal of pharmacology 20121101

Title: Peloruside, laulimalide, and noscapine interactions with beta-tubulin.

Journal: Pharmaceutical research 20121101

Title: Induction of robust de novo centrosome amplification, high-grade spindle multipolarity and metaphase catastrophe: a novel chemotherapeutic approach.

Journal: Cell death & disease 20120701

Title: A Papaver somniferum 10-gene cluster for synthesis of the anticancer alkaloid noscapine.

Journal: Science (New York, N.Y.) 20120629

Title: Plant science. Plant gene clusters and opiates.

Journal: Science (New York, N.Y.) 20120629

Title: Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy.

Journal: Plant physiology 20120601

Title: Noscapine induces mitochondria-mediated apoptosis in human colon cancer cells in vivo and in vitro.

Journal: Biochemical and biophysical research communications 20120511

Title: Molecular cycloencapsulation augments solubility and improves therapeutic index of brominated noscapine in prostate cancer cells.

Journal: Molecular pharmaceutics 20120507

Title: Copper(I) mediated facile synthesis of potent tubulin polymerization inhibitor, 9-amino-α-noscapine from natural α-noscapine.

Journal: Bioorganic & medicinal chemistry letters 20120415

Title: Tubulin binding, protein-bound conformation in solution, and antimitotic cellular profiling of noscapine and its derivatives.

Journal: Journal of medicinal chemistry 20120308

Title: In silico inspired design and synthesis of a novel tubulin-binding anti-cancer drug: folate conjugated noscapine (Targetin).

Journal: Journal of computer-aided molecular design 20120201

Title: Noscapinoids with anti-cancer activity against human acute lymphoblastic leukemia cells (CEM): a three dimensional chemical space pharmacophore modeling and electronic feature analysis.

Journal: Journal of molecular modeling 20120101

Title: Exposure of consumers to morphine from poppy seeds in Hungary.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20120101

Title: Noscapine induced apoptosis via downregulation of survivin in human neuroblastoma cells having wild type or null p53.

Journal: PloS one 20120101

Title: Noscapine inhibits tumor growth in TMZ-resistant gliomas.

Journal: Cancer letters 20111222

Title: Determination of noscapine's localization and interaction with the tubulin-α/β heterodimer.

Journal: Chemical biology & drug design 20111001

Title: Rational design of novel anti-microtubule agent (9-azido-noscapine) from quantitative structure activity relationship (QSAR) evaluation of noscapinoids.

Journal: Journal of biomolecular screening 20111001

Title: Second generation benzofuranone ring substituted noscapine analogs: synthesis and biological evaluation.

Journal: Biochemical pharmacology 20110715

Title: Long-circulating poly(ethylene glycol)-grafted gelatin nanoparticles customized for intracellular delivery of noscapine: preparation, in-vitro characterization, structure elucidation, pharmacokinetics, and cytotoxicity analyses.

Journal: Anti-cancer drugs 20110701

Title: Noscapine sensitizes chemoresistant ovarian cancer cells to cisplatin through inhibition of HIF-1α.

Journal: Cancer letters 20110601

Title: Molecular modelling and competition binding study of Br-noscapine and colchicine provide insight into noscapinoid-tubulin binding site.

Journal: Journal of molecular graphics & modelling 20110601

Title: Rational design, synthesis and biological evaluations of amino-noscapine: a high affinity tubulin-binding noscapinoid.

Journal: Journal of computer-aided molecular design 20110501

Title: Noscapine induces mitochondria-mediated apoptosis in gastric cancer cells in vitro and in vivo.

Journal: Cancer chemotherapy and pharmacology 20110301

Title: Anticancer activity of Noscapine, an opioid alkaloid in combination with Cisplatin in human non-small cell lung cancer.

Journal: Lung cancer (Amsterdam, Netherlands) 20110301

Title: Fixed drug eruption caused by noscapine.

Journal: The Journal of dermatology 20110301

Title: Enhanced noscapine delivery using uPAR-targeted optical-MR imaging trackable nanoparticles for prostate cancer therapy.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20110210

Title: Antitumor activity of Noscapine in combination with Doxorubicin in triple negative breast cancer.

Journal: PloS one 20110101

Title: Predicting P-glycoprotein-mediated drug transport based on support vector machine and three-dimensional crystal structure of P-glycoprotein.

Journal: PloS one 20110101

Title: Enhanced anticancer activity of gemcitabine in combination with noscapine via antiangiogenic and apoptotic pathway against non-small cell lung cancer.

Journal: PloS one 20110101

Title: Analysis of omnoponum by surface-ionization mass spectrometry and liquid chromatography tandem mass spectrometry methods.

Journal: Journal of pharmaceutical and biomedical analysis 20101201

Title: Clinically significant CYP2C inhibition by noscapine but not by glucosamine.

Journal: Clinical pharmacology and therapeutics 20100901

Title: Evaluation of ligand-selector interaction from effective diffusion coefficient.

Journal: Analytical chemistry 20100701

Title: Efficacy and safety of modified sequential three-step empirical therapy for chronic cough.

Journal: Respirology (Carlton, Vic.) 20100701

Title: Induction of reactive oxygen species-mediated autophagy by a novel microtubule-modulating agent.

Journal: The Journal of biological chemistry 20100611

Title: Noscapine, a benzylisoquinoline alkaloid, sensitizes leukemic cells to chemotherapeutic agents and cytokines by modulating the NF-kappaB signaling pathway.

Journal: Cancer research 20100415

Title: Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics.

Journal: Cancer chemotherapy and pharmacology 20100201

Title: Simultaneous chemiluminescence determination of thebaine and noscapine using support vector machine regression.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100201

Title: Time-dependent inhibition (TDI) of CYP3A4 and CYP2C9 by noscapine potentially explains clinical noscapine-warfarin interaction.

Journal: British journal of clinical pharmacology 20100201

Title: Prophylactic noscapine therapy inhibits human prostate cancer progression and metastasis in a mouse model.

Journal: Anticancer research 20100201

Title: Potent anti-inflammatory activity of novel microtubule-modulating brominated noscapine analogs.

Journal: PloS one 20100101

Title: Human serum albumin nanoparticles as an efficient noscapine drug delivery system for potential use in breast cancer: preparation and in vitro analysis.

Journal: International journal of nanomedicine 20100101

Title: Relevance of an opioid, noscapine in reducing cystogeneses in rat experimental model of polycystic ovary syndrome.

Journal: Journal of endocrinological investigation 20091101

Title: Recent patents reveal microtubules as persistent promising target for novel drug development for cancers.

Journal: Recent patents on anti-infective drug discovery 20091101

Title: General unknown screening procedure for the characterization of human drug metabolites in forensic toxicology: applications and constraints.

Journal: Journal of separation science 20090901

Title: Validated stability-indicating TLC method for the determination of noscapine.

Journal: Drug testing and analysis 20090701

Title: 9-bromonoscapine-induced mitotic arrest of cigarette smoke condensate-transformed breast epithelial cells.

Journal: Journal of cellular biochemistry 20090415

Title: [Noscapine and warfarin--a potentially dangerous interaction].

Journal: Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke 20090312

Title: Simultaneous determination of codeine and noscapine by flow-injection chemiluminescence method using N-PLS regression.

Journal: Journal of pharmaceutical and biomedical analysis 20090220

Title: The anti-cancer activity of noscapine: a review.

Journal: Recent patents on anti-cancer drug discovery 20090101

Title: Antitumor activity of noscapine in human non-small cell lung cancer xenograft model.

Journal: Cancer chemotherapy and pharmacology 20081201

Title: Fragmentation pathways of heroin-related alkaloids revealed by ion trap and quadrupole time-of-flight tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20080901

Title: Antiangiogenic effects of noscapine enhance radioresponse for GL261 tumors.

Journal: International journal of radiation oncology, biology, physics 20080801

Title: Effect of noscapine and vincristine combination on demyelination and cell proliferation in vitro.

Journal: Leukemia & lymphoma 20080801

Title: Noscapine induces apoptosis in human glioma cells by an apoptosis-inducing factor-dependent pathway.

Journal: Anti-cancer drugs 20080701

Title: Warfarin-noscapine interaction: a series of four case reports.

Journal: The Annals of pharmacotherapy 20080301

Title: Noscapine may increase the effect of warfarin.

Journal: British journal of clinical pharmacology 20080201

Title: Noscapine inhibits human prostate cancer progression and metastasis in a mouse model.

Journal: Anticancer research 20080101

Title: Simultaneous voltammetric determination of morphine and noscapine by adsorptive differential pulse stripping method and least-squares support vector machines.

Journal: Talanta 20071130

Title: Preclinical pharmacokinetics and bioavailability of noscapine, a tubulin-binding anticancer agent.

Journal: Cancer chemotherapy and pharmacology 20071101

Title: Apoptotic pathway induced by noscapine in human myelogenous leukemic cells.

Journal: Anti-cancer drugs 20071101

Title: Separation and determination of five major opium alkaloids with mixed mode of hydrophilic/cation-exchange monolith by pressurized capillary electrochromatography.

Journal: Journal of separation science 20071101

Title: A simple and rapid flow-injection chemiluminescence method for the determination of noscapine with Ru(phen)3(2+)-Ce(IV) system.

Journal: Annali di chimica 20070801

Title: p53 and p21 determine the sensitivity of noscapine-induced apoptosis in colon cancer cells.

Journal: Cancer research 20070415

Title: Validation of meconin as a marker for illicit opiate use.

Journal: Journal of analytical toxicology 20070301

Title: Synthesis and biological evaluation of a cyclic ether fluorinated noscapine analog.

Journal: Bioorganic & medicinal chemistry 20061215

Title: The use of CE-electrochemiluminescence with ionic liquid for the determination of bioactive constituents in Chinese traditional medicine.

Journal: Electrophoresis 20061201

Title: Synthesis and in vitro cytotoxicity of haloderivatives of noscapine.

Journal: Bioorganic & medicinal chemistry 20061001

Title: Treatment of hormone-refractory breast cancer: apoptosis and regression of human tumors implanted in mice.

Journal: Molecular cancer therapeutics 20060901

Title: Synthesis of microtubule-interfering halogenated noscapine analogs that perturb mitosis in cancer cells followed by cell death.

Journal: Biochemical pharmacology 20060814

Title: The significance of putative urinary markers of illicit heroin use after consumption of poppy seed products.

Journal: Therapeutic drug monitoring 20060801

Title: Development of a novel nitro-derivative of noscapine for the potential treatment of drug-resistant ovarian cancer and T-cell lymphoma.

Journal: Molecular pharmacology 20060601

Title: Noscapine inhibits hypoxia-mediated HIF-1alpha expression andangiogenesis in vitro: a novel function for an old drug.

Journal: International journal of oncology 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Application of poly(methacrylic acid-ethylene glycol dimethacrylate) monolith microextraction coupled with capillary zone electrophoresis to the determination of opiates in human urine.

Journal: Electrophoresis 20060501

Title: Noscapine and diltiazem augment taxol and radiation-induced S-phase arrest and clonogenic death of C6 glioma in vitro.

Journal: Surgical neurology 20060501

Title: Rational design of the microtubule-targeting anti-breast cancer drug EM015.

Journal: Cancer research 20060401

Title: Atmospheric pressure ionisation mass spectrometric fragmentation pathways of noscapine and papaverine revealed by multistage mass spectrometry and in-source deuterium labelling.

Journal: Rapid communications in mass spectrometry : RCM 20060101

Title: Anxiolytic effect of noscapine in mice.

Journal: Pharmacological reports : PR 20060101

Title: Identification of novel and improved antimitotic agents derived from noscapine.

Journal: Journal of medicinal chemistry 20051117

Title: [Analysis of two year heroin seizures in the Liege area].

Journal: Revue medicale de Liege 20050901

Title: Noscapine suppresses angiotensin converting enzyme inhibitors-induced cough.

Journal: Nephrology (Carlton, Vic.) 20050801

Title: Principal opium alkaloids as possible biochemical markers for the source identification of Indian opium.

Journal: Journal of separation science 20050801

Title: Synthesis and radioligand binding studies of C-5- and C-8-substituted 1-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK channel blockers related to N-methyl-laudanosine and N-methyl-noscapine.

Journal: Journal of medicinal chemistry 20050728

Title: Simultaneous determination of methylephedrine and noscapine in human plasma by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050625

Title: Discovery of S-phase arresting agents derived from noscapine.

Journal: Journal of medicinal chemistry 20050421

Title: Development and validation of a capillary electrophoresis method for the determination of codeine, diphenhydramine, ephedrine and noscapine in pharmaceuticals.

Journal: Farmaco (Societa chimica italiana : 1989) 20050101

Title: Targeting microtubules for cancer chemotherapy.

Journal: Current medicinal chemistry. Anti-cancer agents 20050101

Title: Thin-layer chromatography-densitometry and liquid chromatography analysis of alkaloids in leaves of Papaver somniferum under stress conditions.

Journal: Journal of AOAC International 20050101

Title: Electrophysiological characterization of the SK channel blockers methyl-laudanosine and methyl-noscapine in cell lines and rat brain slices.

Journal: British journal of pharmacology 20041101

Title: Noscapine crosses the blood-brain barrier and inhibits glioblastoma growth.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040801

Title: Modulatory influence of noscapine on the ethanol-altered hepatic biotransformation system enzymes, glutathione content and lipid peroxidation in vivo in rats.

Journal: European journal of drug metabolism and pharmacokinetics 20040101

Title: A preliminary report on the application of noscapine in the treatment of stroke.

Journal: European journal of clinical pharmacology 20031101

Title: [Acute higher funghi mushroom poisoning and its treatment].

Journal: Presse medicale (Paris, France : 1983) 20030920

Title: HPLC determination of aminophylline, methoxyphenamine hydrochloride, noscapine and chlorphenamine maleate in compound dosage forms with an aqueous-organic mobile phase.

Journal: Journal of pharmaceutical and biomedical analysis 20030915

Title: Noscapine hydrochloride-induced numerical aberrations in cultured human lymphocytes: a comparison of FISH detection methods and multiple end-points.

Journal: Mutagenesis 20030501

Title: Application of capillary zone electrophoresis in the separation and determination of the principal gum opium alkaloids.

Journal: Electrophoresis 20030501

Title: Brominated derivatives of noscapine are potent microtubule-interfering agents that perturb mitosis and inhibit cell proliferation.

Journal: Molecular pharmacology 20030401

Title: Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor.

Journal: Analytical and bioanalytical chemistry 20030401

Title: Flow injection determination of papaverine based on its sensitizing effect on the chemiluminescence reaction of permanganate-sulfite.

Journal: Analytical and bioanalytical chemistry 20030101

Title: Interaction of noscapine with the bradykinin mediation of the cough response.

Journal: Acta physiologica Hungarica 20030101

Title: Reduction of the prenatal hypoxic-ischemic brain edema with noscapine.

Journal: Acta physiologica Hungarica 20030101

Title: [Influence of fertilizers on yield and yield components of opium from Papaver somniferum Linn].

Journal: Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo hokoku = Bulletin of National Institute of Health Sciences 20030101

Title: Enhancing the in vitro and in vivo detection of aneuploidy by fluorescence in situ hybridization with the use of bromodeoxyuridine as a proliferation marker.

Journal: Mutation research 20021126

Title: Paclitaxel-resistant human ovarian cancer cells undergo c-Jun NH2-terminal kinase-mediated apoptosis in response to noscapine.

Journal: The Journal of biological chemistry 20021018

Title: Noscapine alters microtubule dynamics in living cells and inhibits the progression of melanoma.

Journal: Cancer research 20020715

Title: Minor alteration of microtubule dynamics causes loss of tension across kinetochore pairs and activates the spindle checkpoint.

Journal: The Journal of biological chemistry 20020510

Title: Mass spectral studies on aryl-substituted N-carbamoyl/N-thiocarbamoyl narcotine and related compounds.

Journal: Rapid communications in mass spectrometry : RCM 20020101

Title: Sustained activation of p34(cdc2) is required for noscapine-induced apoptosis.

Journal: The Journal of biological chemistry 20011214

Title: Characterization of an unknown component in Noscapine using liquid chromatography-mass spectrometry and proton nuclear magnetic resonance spectroscopy.

Journal: Journal of chromatography. A 20010824

Title: Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.

Journal: Journal of chromatography. A 20010727

Title: Peripheral T-cell lymphoma with aberrant expression of CD79a and CD20: a diagnostic pitfall.

Journal: Modern pathology : an official journal of the United States and Canadian Academy of Pathology, Inc 20010201

Title: [Guillain-Barre syndrome as a result of poisoning with a mixture of 'kompot'(Polish heroin) and drugs].

Journal: Przeglad lekarski 20010101

Title: Efffect of noscapine, the antitussive opioid alkaloid, on bradykinin-induced smooth muscle contraction in the isolated ileum of the guinea-pig.

Journal: Acta physiologica Hungarica 20010101

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SDS
Tags:10421-76-8 Molecular Formula|10421-76-8 MDL|10421-76-8 SMILES|10421-76-8 6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3h-isobenzofuran-1-one