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38819-10-2,MFCD12912394
Catalog No.:AA0037UQ

38819-10-2 | 9-(Beta-d-arabinofuranosyl)guanine

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50mg
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100mg
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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0037UQ
Chemical Name:
9-(Beta-d-arabinofuranosyl)guanine
CAS Number:
38819-10-2
Molecular Formula:
C10H13N5O5
Molecular Weight:
283.2407
MDL Number:
MFCD12912394
SMILES:
OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1nc(N)[nH]c2=O
Properties
Computed Properties
 
Complexity:
446  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
2  
XLogP3:
-1.9  

Downstream Synthesis Route

[1]JournalofHeterocyclicChemistry,1988,vol.25,p.1899-1903

[2]BiochemicalPharmacology,1995,vol.50,p.163-168

[1]Tetrahedron,1984,vol.40,p.125-135

[1]HelveticaChimicaActa,1993,vol.76,p.158-167

[1]JournalofHeterocyclicChemistry,1988,vol.25,p.1899-1903

[1]PharmaceuticalChemistryJournal,1985,vol.19,p.259-261    Khimiko-FarmatsevticheskiiZhurnal,1985,vol.19,p.425-427

Literature

Title: Induction of fetal hemoglobin and ABCB1 gene expression in 9-β-D-arabinofuranosylguanine-resistant MOLT-4 cells.

Journal: Cancer chemotherapy and pharmacology 20110901

Title: In vitro efficacy of forodesine and nelarabine (ara-G) in pediatric leukemia.

Journal: Blood 20110825

Title: Activation of guanine-β-D-arabinofuranoside and deoxyguanosine to triphosphates by a common pathway blocks T lymphoblasts at different checkpoints.

Journal: Experimental cell research 20101210

Title: A new high-performance liquid chromatography method determines low production of 9-beta-D-arabinofuranosylguanine triphosphate, an active metabolite of nelarabine, in adult T-cell leukemia cells.

Journal: Oncology reports 20100201

Title: Intravitreal crystalline drug delivery for intraocular proliferation diseases.

Journal: Investigative ophthalmology & visual science 20100101

Title: Nelarabine in the treatment of refractory T-cell malignancies.

Journal: Clinical Medicine Insights. Oncology 20100101

Title: Acute cytotoxicity of arabinofuranosyl nucleoside analogs is not dependent on mitochondrial DNA.

Journal: Experimental cell research 20090910

Title: Synthesis of 9-beta-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts.

Journal: Bioorganic & medicinal chemistry letters 20090801

Title: Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia.

Journal: OncoTargets and therapy 20090101

Title: Reduced levels of mitochondrial DNA increases the toxicity of 9-beta-D-arabinofuranosylguanine (araG).

Journal: Nucleosides, nucleotides & nucleic acids 20080601

Title: Nelarabine.

Journal: Drugs 20080101

Title: Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma.

Journal: Therapeutics and clinical risk management 20071201

Title: Nelarabine: a novel purine antimetabolite antineoplastic agent.

Journal: Clinical therapeutics 20070901

Title: Depletion of mitochondrial DNA by down-regulation of deoxyguanosine kinase expression in non-proliferating HeLa cells.

Journal: Experimental cell research 20070715

Title: Nelarabine induces complete remissions in adults with relapsed or refractory T-lineage acute lymphoblastic leukemia or lymphoblastic lymphoma: Cancer and Leukemia Group B study 19801.

Journal: Blood 20070615

Title: Cell cycle effect on the activity of deoxynucleoside analogue metabolising enzymes.

Journal: Biochemical and biophysical research communications 20070615

Title: Plasma and cerebrospinal fluid pharmacokinetics of nelarabine in nonhuman primates.

Journal: Cancer chemotherapy and pharmacology 20070501

Title: Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.

Journal: Bioorganic & medicinal chemistry 20070415

Title: Enhanced toxicity of purine nucleoside analogs in cells expressing Drosophila melanogaster nucleoside kinase mutants.

Journal: Gene therapy 20070101

Title: Results of a phase II study of 506U78 in cutaneous T-cell lymphoma and peripheral T-cell lymphoma: CALGB 59901.

Journal: Leukemia & lymphoma 20070101

Title: Nelarabine: a new purine analog in the treatment of hematologic malignancies.

Journal: Reviews on recent clinical trials 20060901

Title: Nelarabine: efficacy in the treatment of clinical malignancies.

Journal: Future oncology (London, England) 20060801

Title: Phosphorylation of 9-beta-D-arabinofuranosylguanine monophosphate by Drosophila melanogaster guanylate kinase.

Journal: Biochemical pharmacology 20051001

Title: Phase II study of nelarabine (compound 506U78) in children and young adults with refractory T-cell malignancies: a report from the Children's Oncology Group.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050520

Title: Phase I study of 506U78 administered on a consecutive 5-day schedule in children and adults with refractory hematologic malignancies.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050520

Title: Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.

Journal: Journal of medicinal chemistry 20040422

Title: Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20040101

Title: Mechanisms for T-cell selective cytotoxicity of arabinosylguanine.

Journal: Blood 20030901

Title: The novel nucleoside transport system exhibited by NB4 cells, csg, transports deoxyguanosine analogues, including ara-G.

Journal: Biochemical pharmacology 20030901

Title: Effects of 9-beta-D-arabinofuranosylguanine on mitochondria in CEM T-lymphoblast leukemia cells.

Journal: Biochemical and biophysical research communications 20030808

Title: Cytosolic and mitochondrial deoxyribonucleotidases: activity with substrate analogs, inhibitors and implications for therapy.

Journal: Biochemical pharmacology 20030801

Title: Resistance to mitochondrial- and Fas-mediated apoptosis in human leukemic cells with acquired resistance to 9-beta-D-arabinofuranosylguanosine.

Journal: Biochemical and biophysical research communications 20021101

Title: Arabinosylguanine is phosphorylated by both cytoplasmic deoxycytidine kinase and mitochondrial deoxyguanosine kinase.

Journal: Cancer research 20020601

Title: Low level of mitochondrial deoxyguanosine kinase is the dominant factor in acquired resistance to 9-beta-D-arabinofuranosylguanine cytotoxicity.

Journal: Biochemical and biophysical research communications 20020524

Title: Telomerase-inhibitory effects of sugar-modified nucleotide analogs.

Journal: Nucleic acids research. Supplement (2001) 20020101

Title: Identification and characterization of human deoxyguanosine kinase cDNA fragments.

Journal: Cancer letters 20010920

Title: Dual mechanisms of 9-beta-D-arabinofuranosylguanine resistance in CEM T-lymphoblast leukemia cells.

Journal: Biochemical and biophysical research communications 20010706

Title: Nucleoside analogues: mechanisms of drug resistance and reversal strategies.

Journal: Leukemia 20010601

Title: Anti-herpesvirus activity profile of 4'-thioarabinofuranosyl purine and uracil nucleosides and activity of 1-beta-D-2'-fluoro-4'-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus.

Journal: Antiviral research 19980801

Title: A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities.

Journal: Journal of medicinal chemistry 19970704

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