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54-25-1,MFCD00006472
Catalog No.:AA003N0C

54-25-1 | 6-Azuridine

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1mg
98%
in stock  
$7.00   $5.00
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10mg
>99.0%(HPLC)
in stock  
$35.00   $24.00
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100mg
98%
in stock  
$58.00   $40.00
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250mg
98%
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$97.00   $68.00
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1g
98%
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$183.00   $128.00
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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:
AA003N0C
Chemical Name:
6-Azuridine
CAS Number:
54-25-1
Molecular Formula:
C8H11N3O6
Molecular Weight:
245.1894
MDL Number:
MFCD00006472
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ncc(=O)[nH]c1=O
Properties
Properties
 
Form:
Solid  
MP:
157-159 °C(lit.);  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
372  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-2.1  

Downstream Synthesis Route

[1]CollectionofCzechoslovakChemicalCommunications,1957,vol.22,p.1330-1332

[1]Holy,A.;Cech,D.[CollectionofCzechoslovakChemicalCommunications,1974,vol.39,p.3157-3167]

[1]Drasar,Pavel;Beranek,Jiri[CollectionofCzechoslovakChemicalCommunications,1988,vol.53,#7,p.1568-1573]

54-25-1   
Lithium;(3aR,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxymethyl-2-oxo-tetrahydro-2λ5-furo3,4-d1,3,2dioxaphosphol-2-olate 
  32350-72-4 

[1]Kavunenko,AntoninaP.;Holy,Antonin[CollectionofCzechoslovakChemicalCommunications,1980,vol.45,#2,p.611-616]

[1]Pratviel;Bernadou;Ha;Meunier;Cros;Meunier;Gillet;Guittet[JournalofMedicinalChemistry,1986,vol.29,#8,p.1350-1355]

Literature

Title: Regioselectivity-reversal in acylation of 6-azauridine catalyzed by Burkholderia cepacia lipase.

Journal: Biotechnology letters 20120101

Title: Dengue virus entry as target for antiviral therapy.

Journal: Journal of tropical medicine 20120101

Title: Quinoline tricyclic derivatives. Design, synthesis and evaluation of the antiviral activity of three new classes of RNA-dependent RNA polymerase inhibitors.

Journal: Bioorganic & medicinal chemistry 20111201

Title: Inhibitors of alphavirus entry and replication identified with a stable Chikungunya replicon cell line and virus-based assays.

Journal: PloS one 20110101

Title: Development of an oral form of azacytidine: 2'3'5'triacetyl-5-azacytidine.

Journal: Chemotherapy research and practice 20110101

Title: Structure-based and ligand-based virtual screening of novel methyltransferase inhibitors of the dengue virus.

Journal: BMC bioinformatics 20110101

Title: Insights into arbovirus evolution and adaptation from experimental studies.

Journal: Viruses 20101201

Title: Historical perspectives in the development of antiviral agents against poxviruses.

Journal: Viruses 20100601

Title: Triplet formation of 6-azauridine and singlet oxygen sensitization with UV light irradiation.

Journal: Physical chemistry chemical physics : PCCP 20100521

Title: Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives.

Journal: Bioorganic & medicinal chemistry 20100415

Title: Six RNA viruses and forty-one hosts: viral small RNAs and modulation of small RNA repertoires in vertebrate and invertebrate systems.

Journal: PLoS pathogens 20100201

Title: Antiviral activity of indole derivatives.

Journal: Antiviral research 20090801

Title: Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives.

Journal: Bioorganic & medicinal chemistry 20090701

Title: Hepatoprotective Activity of Licorice Water Extract against Cadmium-induced Toxicity in Rats.

Journal: Evidence-based complementary and alternative medicine : eCAM 20090601

Title: Transcript elongation factor TFIIS is involved in arabidopsis seed dormancy.

Journal: Journal of molecular biology 20090227

Title: Recognition of acyl donors by lipase CAL-B in the acylation of 6-azauridine.

Journal: Biotechnology progress 20090101

Title: Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

Journal: Journal of medicinal chemistry 20081113

Title: Antimicrobial and cytotoxic arylazoenamines. Part III: antiviral activity of selected classes of arylazoenamines.

Journal: Bioorganic & medicinal chemistry 20080915

Title: Structure and inhibition of orotidine 5'-monophosphate decarboxylase from Plasmodium falciparum.

Journal: Biochemistry 20080325

Title: Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae.

Journal: Bioorganic & medicinal chemistry 20080301

Title: Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.

Journal: Journal of medicinal chemistry 20080214

Title: 6-Azauracil or 8-aza-7-deazaadenine nucleosides and oligonucleotides: the effect of 2'-fluoro substituents and nucleobase nitrogens on conformation and base pairing.

Journal: Organic & biomolecular chemistry 20080207

Title: N-methylisatin-beta-thiosemicarbazone derivative (SCH 16) is an inhibitor of Japanese encephalitis virus infection in vitro and in vivo.

Journal: Virology journal 20080101

Title: Azacytidine (Vidaza(R)) in the treatment of myelodysplastic syndromes.

Journal: Therapeutics and clinical risk management 20061201

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: Broad-spectrum inhibitor of viruses in the Flaviviridae family.

Journal: Antiviral research 20051101

Title: Synthesis of N3-substituted uridine and related pyrimidine nucleosides and their antinociceptive effects in mice.

Journal: Chemical & pharmaceutical bulletin 20050301

Title: Comprehensive analysis of risk factors associating with Hepatitis B virus (HBV) reactivation in cancer patients undergoing cytotoxic chemotherapy.

Journal: British journal of cancer 20040405

Title: A simple assay for determining antiviral activity against Crimean-Congo hemorrhagic fever virus.

Journal: Antiviral research 20040401

Title: In vitro inhibition of Chikungunya and Semliki Forest viruses replication by antiviral compounds: synergistic effect of interferon-alpha and ribavirin combination.

Journal: Antiviral research 20040201

Title: [Biotechnological synthesis of ribavirin. Effect of ribavirin and its various combinations on the reproduction of Vaccinia virus].

Journal: Bioorganicheskaia khimiia 20040101

Title: Use of nucleotide analogs by class I and class II CCA-adding enzymes (tRNA nucleotidyltransferase): deciphering the basis for nucleotide selection.

Journal: RNA (New York, N.Y.) 20030801

Title: Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus.

Journal: Lancet (London, England) 20030614

Title: Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses.

Journal: Antiviral research 20030301

Title: Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.

Journal: Journal of virological methods 20021001

Title: Identification of active antiviral compounds against a New York isolate of West Nile virus.

Journal: Antiviral research 20020701

Title: In vitro metabolism studies of the prodrug, 2',3',5'-triacetyl-6-azauridine, utilizing an automated analytical system.

Journal: Journal of pharmaceutical and biomedical analysis 20011201

Title: Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.

Journal: Journal of medicinal chemistry 20011108

Title: Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro.

Journal: Antiviral chemistry & chemotherapy 20011101

Title: Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases.

Journal: Molecular pharmacology 20010501

Title: Site specific incorporation of 6-azauridine into the genomic HDV ribozyme active site.

Journal: Nucleosides, nucleotides & nucleic acids 20010101

Title: Some 6-aza-5-substituted-2'-deoxyuridines show potent and selective inhibition of herpes simplex virus type 1 thymidine kinase.

Journal: Nucleosides & nucleotides 19980101

Title: Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.

Journal: Research in virology 19970101

Title: Central depressant effects of N3-substituted 6-azauridines in mice.

Journal: Chemical & pharmaceutical bulletin 19911001

Title: Broad-spectrum antiviral and cytocidal activity of cyclopentenylcytosine, a carbocyclic nucleoside targeted at CTP synthetase.

Journal: Biochemical pharmacology 19910615

Title: Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro.

Journal: Antiviral research 19890901

Title: Anemia of azaribine in the treatment of psoriasis.

Journal: Archives of dermatology 19761201

Title: Systemic chemotherapy for psoriasis: a national survey.

Journal: Archives of dermatology 19760701

Title: Chemotherapy of psoriasis: ten years of experience.

Journal: International journal of dermatology 19760601

Title: Treatment of psoriatic arthritis with azaribine.

Journal: Arthritis and rheumatism 19760101

Title: Azaribine therapy for psoriasis. Evaluation of potential effects on the liver and other organ systems.

Journal: Archives of dermatology 19750701

Title: Double-blind controlled crossover high-dose study of Azaribine in psoriasis.

Journal: The British journal of dermatology 19750201

Title: The treatment of psoriasis with azaribine.

Journal: Dermatologica 19750101

Title: Herpes simplex virus skin infection in hairless mice: treatment with antiviral compounds.

Journal: Antimicrobial agents and chemotherapy 19740301

Title: 6-Azauridine in combination chemotherapy of childhood acute myelocytic leukemia.

Journal: Cancer 19720401

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