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342-69-8,MFCD00022826
Catalog No.:AA00C0H7

342-69-8 | (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol

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100mg
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$179.00   $125.00
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250mg
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$250.00   $175.00
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500mg
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$340.00   $238.00
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1g
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2g
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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:
AA00C0H7
Chemical Name:
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol
CAS Number:
342-69-8
Molecular Formula:
C11H14N4O4S
Molecular Weight:
298.3183
MDL Number:
MFCD00022826
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2SC
Properties
Properties
 
Form:
Solid  
MP:
166°C  
Refractive Index:
1.6270 (estimate)  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
352  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
0.1  

Downstream Synthesis Route

[1]Hamptonetal.[JournaloftheAmericanChemicalSociety,1956,vol.78,p.5695]

574-25-4   
S-(5′-adenosyl)-L-methioninechloride 
  342-69-8 

[1]MolecularPharmacology,1995,vol.47,p.1141-1147

[1]Bookser,BrettC.;Raffaele,NicholasB.[JournalofOrganicChemistry,2007,vol.72,#1,p.173-179]

[1]JournaloftheAmericanChemicalSociety,1995,vol.117,p.5951-5957

[2]Synthesis,1986,p.450-453

Literature

Title: Simultaneous quantification of eleven thiopurine nucleotides by liquid chromatography-tandem mass spectrometry.

Journal: Analytical chemistry 20120207

Title: Methylthioinosine phosphorylase from Pseudomonas aeruginosa. Structure and annotation of a novel enzyme in quorum sensing.

Journal: Biochemistry 20110222

Title: A thiopurine drug inhibits West Nile virus production in cell culture, but not in mice.

Journal: PloS one 20110101

Title: Crystallographic and docking studies of purine nucleoside phosphorylase from Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry 20100701

Title: Health-related quality of life of youth with inflammatory bowel disease: a comparison with published data using the PedsQL 4.0 generic core scales.

Journal: Inflammatory bowel diseases 20100601

Title: Constrained NBMPR analogue synthesis, pharmacophore mapping and 3D-QSAR modeling of equilibrative nucleoside transporter 1 (ENT1) inhibitory activity.

Journal: Bioorganic & medicinal chemistry 20080401

Title: Thiopurines inhibit bovine viral diarrhea virus production in a thiopurine methyltransferase-dependent manner.

Journal: The Journal of general virology 20080401

Title: Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents.

Journal: Bioorganic & medicinal chemistry letters 20070501

Title: Identification of an in vivo inhibitor of Bacillus anthracis spore germination.

Journal: The Journal of biological chemistry 20070420

Title: [Monitoring of thiopurine methyltransferase and thiopurine metabolites to optimize azathioprine therapy in inflammatory bowel disease].

Journal: Gastroenterologia y hepatologia 20061101

Title: Molecular mechanisms underlying the enhanced sensitivity of thiopurine-resistant T-lymphoblastic cell lines to methyl mercaptopurineriboside.

Journal: Biochemical pharmacology 20060928

Title: A prospective, open-label trial of 6-thioguanine in patients with ulcerative or indeterminate colitis.

Journal: Scandinavian journal of gastroenterology 20051001

Title: Improved synthesis of beta-D-6-methylpurine riboside and antitumor effects of the beta-D- and alpha-D-anomers.

Journal: Molecules (Basel, Switzerland) 20050831

Title: Targeting a novel Plasmodium falciparum purine recycling pathway with specific immucillins.

Journal: The Journal of biological chemistry 20050311

Title: Synthesis of oligoribonucleotides containing N6-alkyladenosine and 2-methylthio-N6-alkyladenosine.

Journal: Current protocols in nucleic acid chemistry 20040901

Title: Plasmodium falciparum purine nucleoside phosphorylase: crystal structures, immucillin inhibitors, and dual catalytic function.

Journal: The Journal of biological chemistry 20040430

Title: Status of methylthioadenosine phosphorylase and its impact on cellular response to L-alanosine and methylmercaptopurine riboside in human soft tissue sarcoma cells.

Journal: Oncology research 20040101

Title: Monitoring of AZA/6-MP treatment in children with IBD is necessary.

Journal: Inflammatory bowel diseases 20031101

Title: Monitoring of azathioprine/6-mercaptopurine treatment in children with IBD is not necessary.

Journal: Inflammatory bowel diseases 20031101

Title: Thiopurine metabolism and identification of the thiopurine metabolites transported by MRP4 and MRP5 overexpressed in human embryonic kidney cells.

Journal: Molecular pharmacology 20021201

Title: ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.

Journal: Journal of medicinal chemistry 20010719

Title: Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.

Journal: Journal of medicinal chemistry 19841101

Title: Synthesis and antiviral activity of certain carbamoylpyrrolopyrimidine and pyrazolopyrimidine nucleosides.

Journal: Journal of medicinal chemistry 19821101

Title: Purine analogs as potential anticytomegalovirus agents.

Journal: Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.) 19690901

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SDS
Tags:342-69-8 Molecular Formula|342-69-8 MDL|342-69-8 SMILES|342-69-8 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol