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329689-23-8,MFCD11978057
Catalog No.:AA00C9ZD

329689-23-8 | DL-Monastrol

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1mg
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5mg
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10mg
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25mg
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C9ZD
Chemical Name:
DL-Monastrol
CAS Number:
329689-23-8
Molecular Formula:
C14H16N2O3S
Molecular Weight:
292.3534
MDL Number:
MFCD11978057
SMILES:
CCOC(=O)C1=C(C)NC(=S)NC1c1cccc(c1)O
NSC Number:
716782
Properties
Computed Properties
 
Complexity:
436  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
1  
XLogP3:
1.6  

Literature

Title: Interference with kinesin-based anterograde neurofilament axonal transport increases neurofilament-neurofilament bundling.

Journal: Cytoskeleton (Hoboken, N.J.) 20120601

Title: Inhibition of Eg5 acts synergistically with checkpoint abrogation in promoting mitotic catastrophe.

Journal: Molecular cancer research : MCR 20120501

Title: Microtubule redistribution in growth cones elicited by focal inactivation of kinesin-5.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120425

Title: The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis.

Journal: Experimental cell research 20120310

Title: Transcription-independent role of Bach1 in mitosis through a nuclear exporter Crm1-dependent mechanism.

Journal: FEBS letters 20120217

Title: A role for metaphase spindle elongation forces in correction of merotelic kinetochore attachments.

Journal: Current biology : CB 20120207

Title: Identification of cytoskeleton-associated proteins essential for lysosomal stability and survival of human cancer cells.

Journal: PloS one 20120101

Title: Chromosome segregation errors as a cause of DNA damage and structural chromosome aberrations.

Journal: Science (New York, N.Y.) 20110930

Title: Synthesis and characterization of tritylthioethanamine derivatives with potent KSP inhibitory activity.

Journal: Bioorganic & medicinal chemistry 20110915

Title: Synthesis and biological evaluation of conformationally flexible as well as restricted dimers of monastrol and related dihydropyrimidones.

Journal: European journal of medicinal chemistry 20110801

Title: Structure-activity relationship and multidrug resistance study of new S-trityl-L-cysteine derivatives as inhibitors of Eg5.

Journal: Journal of medicinal chemistry 20110324

Title: Inhibition of Kinesin-5, a microtubule-based motor protein, as a strategy for enhancing regeneration of adult axons.

Journal: Traffic (Copenhagen, Denmark) 20110301

Title: Loop 5-directed compounds inhibit chimeric kinesin-5 motors: implications for conserved allosteric mechanisms.

Journal: The Journal of biological chemistry 20110225

Title: High-content analysis in monastrol suppressor screens. A neural network-based classification approach.

Journal: Methods of information in medicine 20110101

Title: Design, synthesis and bioevaluation of dihydropyrazolo[3,4-b]pyridine and benzo[4,5]imidazo[1,2-a]pyrimidine compounds as dual KSP and Aurora-A kinase inhibitors for anti-cancer agents.

Journal: Bioorganic & medicinal chemistry 20101115

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

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Structural basis for inhibition of Eg5 by dihydropyrimidines: stereoselectivity of antimitotic inhibitors enastron, dimethylenastron and fluorastrol.

Journal: Journal of medicinal chemistry 20100812

Title: Molecular docking, structure-activity relationship and biological evaluation of the anticancer drug monastrol as a pteridine reductase inhibitor in a clinical isolate of Leishmania donovani.

Journal: The Journal of antimicrobial chemotherapy 20100801

Title: Enantioselective biocatalytic synthesis of (S)-monastrol.

Journal: Bioorganic & medicinal chemistry letters 20100801

Title: Monastrol analogs: a synthesis of pyrazolopyridine, benzopyranopyrazolopyridine, and oxygen-bridged azolopyrimidine derivatives and their biological screening.

Journal: Bioorganic & medicinal chemistry letters 20100715

Title: Dihydropyrimidinone positive modulation of delta-subunit-containing gamma-aminobutyric acid type A receptors, including an epilepsy-linked mutant variant.

Journal: Biochemistry 20100615

Title: The effect of monastrol on the processive motility of a dimeric kinesin-5 head/kinesin-1 stalk chimera.

Journal: Journal of molecular biology 20100528

Title: Search for new and novel chemotherapeutics for the treatment of human malignancies.

Journal: Mini reviews in medicinal chemistry 20100501

Title: Design and in vitro evaluation of branched peptide conjugates: turning nonspecific cytotoxic drugs into tumor-selective agents.

Journal: ChemMedChem 20100406

Title: Mutations in the human kinesin Eg5 that confer resistance to monastrol and S-trityl-L-cysteine in tumor derived cell lines.

Journal: Biochemical pharmacology 20100315

Title: Interplay of microtubule dynamics and sliding during bipolar spindle formation in mammalian cells.

Journal: Current biology : CB 20091229

Title: Thermodynamics of nucleotide and inhibitor binding to wild-type and ispinesib-resistant forms of human kinesin spindle protein.

Journal: Biochemistry 20091124

Title: NSC 622124 inhibits human Eg5 and other kinesins via interaction with the conserved microtubule-binding site.

Journal: Biochemistry 20090303

Title: Kinesin-5 is essential for growth-cone turning.

Journal: Current biology : CB 20081223

Title: Design and synthesis of 2-amino-pyrazolopyridines as Polo-like kinase 1 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20081015

Title: Crystal structure of HsEg5 in complex with clinical candidate CK0238273 provides insight into inhibitory mechanism, potency, and specificity.

Journal: Biochemical and biophysical research communications 20080808

Title: Progress on kinesin spindle protein inhibitors as anti-cancer agents.

Journal: Anti-cancer agents in medicinal chemistry 20080801

Title: The centromere geometry essential for keeping mitosis error free is controlled by spindle forces.

Journal: Nature 20071129

Title: New chemical tools for investigating human mitotic kinesin Eg5.

Journal: Bioorganic & medicinal chemistry 20071001

Title: [Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20071001

Title: Docking studies on kinesin spindle protein inhibitors: an important cooperative 'minor binding pocket' which increases the binding affinity significantly.

Journal: Journal of molecular modeling 20070901

Title: Estrogen-dependent regulation of Eg5 in breast cancer cells.

Journal: Anti-cancer drugs 20070801

Title: Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush-type chiral stationary phases.

Journal: Chirality 20070601

Title: Structure of human Eg5 in complex with a new monastrol-based inhibitor bound in the R configuration.

Journal: The Journal of biological chemistry 20070330

Title: Myosin IIA regulates cell motility and actomyosin-microtubule crosstalk.

Journal: Nature cell biology 20070301

Title: Inhibitors of kinesin Eg5: antiproliferative activity of monastrol analogues against human glioblastoma cells.

Journal: Cancer chemotherapy and pharmacology 20070201

Title: Potentiation of kinesin spindle protein inhibitor-induced cell death by modulation of mitochondrial and death receptor apoptotic pathways.

Journal: Cancer research 20070101

Title: Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis.

Journal: Nature protocols 20070101

Title: Induction of apoptosis by monastrol, an inhibitor of the mitotic kinesin Eg5, is independent of the spindle checkpoint.

Journal: Molecular cancer therapeutics 20061001

Title: Allosteric inhibition of kinesin-5 modulates its processive directional motility.

Journal: Nature chemical biology 20060901

Title: Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: Monastrol, oxo-monastrol and oxygenated analogues.

Journal: Bioorganic chemistry 20060801

Title: Molecular dissection of the inhibitor binding pocket of mitotic kinesin Eg5 reveals mutants that confer resistance to antimitotic agents.

Journal: Journal of molecular biology 20060707

Title: A structural model for monastrol inhibition of dimeric kinesin Eg5.

Journal: The EMBO journal 20060517

Title: A computerized cellular imaging system for high content analysis in Monastrol suppressor screens.

Journal: Journal of biomedical informatics 20060401

Title: A pathway of structural changes produced by monastrol binding to Eg5.

Journal: The Journal of biological chemistry 20060324

Title: Chromosomes can congress to the metaphase plate before biorientation.

Journal: Science (New York, N.Y.) 20060120

Title: Interaction of the mitotic kinesin Eg5 inhibitor monastrol with P-glycoprotein.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20060101

Title: Kinesin-5 motors are required for organization of spindle microtubules in Silvetia compressa zygotes.

Journal: BMC plant biology 20060101

Title: ATPase mechanism of Eg5 in the absence of microtubules: insight into microtubule activation and allosteric inhibition by monastrol.

Journal: Biochemistry 20051220

Title: Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: asymmetric synthesis of dihydropyrimidines.

Journal: Journal of the American Chemical Society 20051130

Title: Application of molecular modeling to analysis of inhibition of kinesin motor proteins of the BimC subfamily by monastrol and related compounds.

Journal: Chemistry & biodiversity 20051101

Title: Development and biological evaluation of potent and specific inhibitors of mitotic Kinesin Eg5.

Journal: Chembiochem : a European journal of chemical biology 20050701

Title: Monastrol inhibition of the mitotic kinesin Eg5.

Journal: The Journal of biological chemistry 20050401

Title: Monastrol, a selective inhibitor of the mitotic kinesin Eg5, induces a distinctive growth profile of dendrites and axons in primary cortical neuron cultures.

Journal: Cell motility and the cytoskeleton 20050401

Title: Mechanism of inhibition of human KSP by monastrol: insights from kinetic analysis and the effect of ionic strength on KSP inhibition.

Journal: Biochemistry 20041207

Title: Identification of the protein binding region of S-trityl-L-cysteine, a new potent inhibitor of the mitotic kinesin Eg5.

Journal: Biochemistry 20041019

Title: Disparity in allosteric interactions of monastrol with Eg5 in the presence of ADP and ATP: a difference FT-IR investigation.

Journal: Biochemistry 20040810

Title: Differential effects of monastrol in two human cell lines.

Journal: Cellular and molecular life sciences : CMLS 20040801

Title: Monastrol stabilises an attached low-friction mode of Eg5.

Journal: Current biology : CB 20040608

Title: Development of high-throughput screens for discovery of kinesin adenosine triphosphatase modulators.

Journal: Analytical biochemistry 20040601

Title: Monastrol, a prototype anti-cancer drug that inhibits a mitotic kinesin, induces rapid bursts of axonal outgrowth from cultured postmitotic neurons.

Journal: Cell motility and the cytoskeleton 20040501

Title: TopBP1 localises to centrosomes in mitosis and to chromosome cores in meiosis.

Journal: Chromosoma 20040501

Title: Transient exposure to the Eg5 kinesin inhibitor monastrol leads to syntelic orientation of chromosomes and aneuploidy in mouse oocytes.

Journal: Mutation research 20040411

Title: Correcting improper chromosome-spindle attachments during cell division.

Journal: Nature cell biology 20040301

Title: Inhibition of a mitotic motor protein: where, how, and conformational consequences.

Journal: Journal of molecular biology 20040109

Title: Combining synthetic and analytical strategies for preparative HPLC enantioseparation of monastrol racemic mixture.

Journal: Biotechnology progress 20040101

Title: Determining the position of the cell division plane.

Journal: Nature 20030828

Title: Survivin is required for a sustained spindle checkpoint arrest in response to lack of tension.

Journal: The EMBO journal 20030616

Title: The small molecule Hesperadin reveals a role for Aurora B in correcting kinetochore-microtubule attachment and in maintaining the spindle assembly checkpoint.

Journal: The Journal of cell biology 20030428

Title: Chemical genetics goes (zebra) fishing.

Journal: Angewandte Chemie (International ed. in English) 20030310

Title: Interaction of the mitotic inhibitor monastrol with human kinesin Eg5.

Journal: Biochemistry 20030121

Title: Decoration of dihydropyrimidine and dihydropyridine scaffolds with sugars via Biginelli and Hantzsch multicomponent reactions: an efficient entry to a collection of artificial nucleosides.

Journal: Molecular diversity 20030101

Title: Evidence that monastrol is an allosteric inhibitor of the mitotic kinesin Eg5.

Journal: Chemistry & biology 20020901

Title: Role of mitotic motors, dynein and kinesin, in the induction of abnormal centrosome integrity and multipolar spindles in cultured V79 cells exposed to dimethylarsinic acid.

Journal: Mutation research 20020129

Title: SIMS ion microscopy in cancer research: single cell isotopic imaging for chemical composition, cytotoxicity and cell cycle recognition.

Journal: Cellular and molecular biology (Noisy-le-Grand, France) 20010501

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Title: Marques LA, et al. Antiproliferative activity of monastrol in human adenocarcinoma (MCF-7) and non-tumor (HB4a) breast cells. Naunyn Schmiedebergs Arch Pharmacol. 2016 Dec;389(12):1279-1288.

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Tags:329689-23-8 Molecular Formula|329689-23-8 MDL|329689-23-8 SMILES|329689-23-8 DL-Monastrol