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38819-10-2

38819-10-2 | 9-β-D-Arabinofuranosylguanine

CAS No: 38819-10-2 Catalog No: AG0037XI MDL No:MFCD00065486

Product Description

Catalog Number:
AG0037XI
Chemical Name:
9-β-D-Arabinofuranosylguanine
CAS Number:
38819-10-2
Molecular Formula:
C10H13N5O5
Molecular Weight:
283.2407
MDL Number:
MFCD00065486
IUPAC Name:
2-amino-9-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
InChI:
InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1
InChI Key:
NYHBQMYGNKIUIF-FJFJXFQQSA-N
SMILES:
OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1nc(N)[nH]c2=O

Properties

Complexity:
446  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
283.092g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
283.244g/mol
Monoisotopic Mass:
283.092g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
155A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.9  

Literature

Title Journal
Induction of fetal hemoglobin and ABCB1 gene expression in 9-β-D-arabinofuranosylguanine-resistant MOLT-4 cells. Cancer chemotherapy and pharmacology 20110901
In vitro efficacy of forodesine and nelarabine (ara-G) in pediatric leukemia. Blood 20110825
Activation of guanine-β-D-arabinofuranoside and deoxyguanosine to triphosphates by a common pathway blocks T lymphoblasts at different checkpoints. Experimental cell research 20101210
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. Oncology reports 20100201
Intravitreal crystalline drug delivery for intraocular proliferation diseases. Investigative ophthalmology & visual science 20100101
Nelarabine in the treatment of refractory T-cell malignancies. Clinical Medicine Insights. Oncology 20100101
Acute cytotoxicity of arabinofuranosyl nucleoside analogs is not dependent on mitochondrial DNA. Experimental cell research 20090910
Synthesis of 9-beta-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts. Bioorganic & medicinal chemistry letters 20090801
Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. OncoTargets and therapy 20090101
Reduced levels of mitochondrial DNA increases the toxicity of 9-beta-D-arabinofuranosylguanine (araG). Nucleosides, nucleotides & nucleic acids 20080601
Nelarabine. Drugs 20080101
Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. Therapeutics and clinical risk management 20071201
Nelarabine: a novel purine antimetabolite antineoplastic agent. Clinical therapeutics 20070901
Depletion of mitochondrial DNA by down-regulation of deoxyguanosine kinase expression in non-proliferating HeLa cells. Experimental cell research 20070715
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. Blood 20070615
Cell cycle effect on the activity of deoxynucleoside analogue metabolising enzymes. Biochemical and biophysical research communications 20070615
Plasma and cerebrospinal fluid pharmacokinetics of nelarabine in nonhuman primates. Cancer chemotherapy and pharmacology 20070501
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity. Bioorganic & medicinal chemistry 20070415
Enhanced toxicity of purine nucleoside analogs in cells expressing Drosophila melanogaster nucleoside kinase mutants. Gene therapy 20070101
Results of a phase II study of 506U78 in cutaneous T-cell lymphoma and peripheral T-cell lymphoma: CALGB 59901. Leukemia & lymphoma 20070101
Nelarabine: a new purine analog in the treatment of hematologic malignancies. Reviews on recent clinical trials 20060901
Nelarabine: efficacy in the treatment of clinical malignancies. Future oncology (London, England) 20060801
Phosphorylation of 9-beta-D-arabinofuranosylguanine monophosphate by Drosophila melanogaster guanylate kinase. Biochemical pharmacology 20051001
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 of clinical oncology : official journal of the American Society of Clinical Oncology 20050520
Phase I study of 506U78 administered on a consecutive 5-day schedule in children and adults with refractory hematologic malignancies. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050520
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase. Journal of medicinal chemistry 20040422
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. Nucleosides, nucleotides & nucleic acids 20040101
Mechanisms for T-cell selective cytotoxicity of arabinosylguanine. Blood 20030901
The novel nucleoside transport system exhibited by NB4 cells, csg, transports deoxyguanosine analogues, including ara-G. Biochemical pharmacology 20030901
Effects of 9-beta-D-arabinofuranosylguanine on mitochondria in CEM T-lymphoblast leukemia cells. Biochemical and biophysical research communications 20030808
Cytosolic and mitochondrial deoxyribonucleotidases: activity with substrate analogs, inhibitors and implications for therapy. Biochemical pharmacology 20030801
Resistance to mitochondrial- and Fas-mediated apoptosis in human leukemic cells with acquired resistance to 9-beta-D-arabinofuranosylguanosine. Biochemical and biophysical research communications 20021101
Arabinosylguanine is phosphorylated by both cytoplasmic deoxycytidine kinase and mitochondrial deoxyguanosine kinase. Cancer research 20020601
Low level of mitochondrial deoxyguanosine kinase is the dominant factor in acquired resistance to 9-beta-D-arabinofuranosylguanine cytotoxicity. Biochemical and biophysical research communications 20020524
Telomerase-inhibitory effects of sugar-modified nucleotide analogs. Nucleic acids research. Supplement (2001) 20020101
Identification and characterization of human deoxyguanosine kinase cDNA fragments. Cancer letters 20010920
Dual mechanisms of 9-beta-D-arabinofuranosylguanine resistance in CEM T-lymphoblast leukemia cells. Biochemical and biophysical research communications 20010706
Nucleoside analogues: mechanisms of drug resistance and reversal strategies. Leukemia 20010601
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. Antiviral research 19980801
A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities. Journal of medicinal chemistry 19970704

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