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20724-73-6,MFCD02682947
Catalog No.:AA002IUE

20724-73-6 | 2'-C-Methylcytidine

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5mg
≥98%
in stock  
$123.00   $86.00
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250mg
98%
in stock  
$178.00   $125.00
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1g
98%
in stock  
$486.00   $340.00
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5g
98%
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$1,607.00   $1,125.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002IUE
Chemical Name:
2'-C-Methylcytidine
CAS Number:
20724-73-6
Molecular Formula:
C10H15N3O5
Molecular Weight:
257.2432
MDL Number:
MFCD02682947
SMILES:
OC[C@H]1O[C@H]([C@]([C@@H]1O)(C)O)n1ccc(nc1=O)N
Properties
Properties
 
BP:
523.9°C at 760 mmHg  
Form:
Solid  
MP:
243-245 °C  
Solubility:
H2O: >20mg/mL  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
424  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-2.4  

Upstream Synthesis Route

[1]OrganicandBiomolecularChemistry,2015,vol.13,#18,p.5158-5174

[2]Patent:WO2015/158913,2015,A1,.Locationinpatent:Page/Pagecolumn37

[1]ChemicalandPharmaceuticalBulletin,1988,vol.36,#3,p.945-953

[2]ChemicalandPharmaceuticalBulletin,1987,vol.35,#9,p.3967-3970

[1]ChemicalandPharmaceuticalBulletin,1987,vol.35,#9,p.3967-3970

[2]ChemicalandPharmaceuticalBulletin,1988,vol.36,#3,p.945-953

[1]ChemicalandPharmaceuticalBulletin,1987,vol.35,#9,p.3967-3970

[2]ChemicalandPharmaceuticalBulletin,1988,vol.36,#3,p.945-953

[1]ChemicalandPharmaceuticalBulletin,1988,vol.36,#3,p.945-953

Downstream Synthesis Route

[1]ChemicalandPharmaceuticalBulletin,1988,vol.36,p.945-953

[2]ChemicalandPharmaceuticalBulletin,1987,vol.35,p.3967-3970

N4-benzoyl-2'-C-methyl-3',5'-di-O-benzoylcytidine 
  20724-73-6 

[1]JournalofMedicinalChemistry,2005,vol.48,p.5504-5508

4637-24-5    20724-73-6   
N4-(dimethylamino)methylene-2'-C-methyl-β-D-cytidine 

[1]Nucleosides,nucleotidesandnucleicacids,2005,vol.24,p.767-770

[2]JournalofMedicinalChemistry,2006,vol.49,p.6614-6620

[1]Nucleosides,nucleotidesandnucleicacids,2005,vol.24,p.767-770

[1]Nucleosides,nucleotidesandnucleicacids,2005,vol.24,p.767-770

[2]JournalofMedicinalChemistry,2006,vol.49,p.6614-6620

[3]Patent:WO2004/58792,2004,A1.Locationinpatent:Page33

Literature

Title: Nucleotide prodrugs of 2'-deoxy-2'-spirooxetane ribonucleosides as novel inhibitors of the HCV NS5B polymerase.

Journal: Journal of medicinal chemistry 20140313

Title: Inhibition of norovirus replication by the nucleoside analogue 2'-C-methylcytidine.

Journal: Biochemical and biophysical research communications 20121102

Title: Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20120615

Title: Anti-hepatitis C virus activity of 3-hydroxy caruilignan C from Swietenia macrophylla stems.

Journal: Journal of viral hepatitis 20120501

Title: Novel substituted 9-norbornylpurines and their activities against RNA viruses.

Journal: Bioorganic & medicinal chemistry letters 20120301

Title: Synthesis and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methyl-7-deazapurine nucleosides, their phosphoramidate prodrugs and 5'-triphosphates.

Journal: Bioorganic & medicinal chemistry letters 20111201

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: Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV.

Journal: European journal of medicinal chemistry 20111001

Title: Synthesis and antiviral activity of cyclopropyl-spirocarbocyclic adenosine, (4R,5S,6R,7R)-4-(6-amino-9H-purin-9-yl)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol against hepatitis C virus.

Journal: Bioorganic & medicinal chemistry letters 20110701

Title: San-Huang-Xie-Xin-Tang extract suppresses hepatitis C virus replication and virus-induced cyclooxygenase-2 expression.

Journal: Journal of viral hepatitis 20110701

Title: Anti-hepatitis C virus activity of Acacia confusa extract via suppressing cyclooxygenase-2.

Journal: Antiviral research 20110101

Title: Antiviral drugs against hepatitis C virus.

Journal: Genetic vaccines and therapy 20110101

Title: 2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase.

Journal: Journal of medicinal chemistry 20101125

Title: Efficacy of 2'-C-methylcytidine against yellow fever virus in cell culture and in a hamster model.

Journal: Antiviral research 20100601

Title: Enhancement of intestinal absorption of 2-methyl cytidine prodrugs.

Journal: Drug delivery 20100501

Title: Evaluation of the role of three candidate human kinases in the conversion of the hepatitis C virus inhibitor 2'-C-methyl-cytidine to its 5'-monophosphate metabolite.

Journal: Antiviral research 20100301

Title: Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.

Journal: Journal of medicinal chemistry 20090910

Title: Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine.

Journal: European journal of medicinal chemistry 20090901

Title: Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase.

Journal: Bioorganic & medicinal chemistry letters 20090301

Title: Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro.

Journal: Journal of medicinal chemistry 20090108

Title: The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors.

Journal: Antimicrobial agents and chemotherapy 20080501

Title: 2'-deoxy-4'-azido nucleoside analogs are highly potent inhibitors of hepatitis C virus replication despite the lack of 2'-alpha-hydroxyl groups.

Journal: The Journal of biological chemistry 20080125

Title: Nitazoxanide, tizoxanide and other thiazolides are potent inhibitors of hepatitis B virus and hepatitis C virus replication.

Journal: Antiviral research 20080101

Title: Combinations of 2'-C-methylcytidine analogues with interferon-alpha2b and triple combination with ribavirin in the hepatitis C virus replicon system.

Journal: Antiviral chemistry & chemotherapy 20080101

Title: Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.

Journal: Bioorganic & medicinal chemistry letters 20070501

Title: 2'-C-methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus.

Journal: Antiviral research 20070301

Title: 2'-C-Methyl branched pyrimidine ribonucleoside analogues: potent inhibitors of RNA virus replication.

Journal: Antiviral chemistry & chemotherapy 20070101

Title: Synthesis and pharmacokinetics of valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine.

Journal: Journal of medicinal chemistry 20061102

Title: Hemin potentiates the anti-hepatitis C virus activity of the antimalarial drug artemisinin.

Journal: Biochemical and biophysical research communications 20060915

Title: In vitro selected Con1 subgenomic replicons resistant to 2'-C-methyl-cytidine or to R1479 show lack of cross resistance.

Journal: Virology 20060801

Title: Synthesis of 3'-beta-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents.

Journal: Organic & biomolecular chemistry 20060407

Title: Nucleoside analog inhibitors of hepatitis C virus replication.

Journal: Infectious disorders drug targets 20060301

Title: The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture.

Journal: The Journal of biological chemistry 20060217

Title: Inhibition of hepatitis C replicon RNA synthesis by beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine: a specific inhibitor of hepatitis C virus replication.

Journal: Antiviral chemistry & chemotherapy 20060101

Title: Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication.

Journal: Journal of medicinal chemistry 20050825

Title: Inhibitory effect of 2'-substituted nucleosides on hepatitis C virus replication correlates with metabolic properties in replicon cells.

Journal: Antimicrobial agents and chemotherapy 20050501

Title: Nm 283, an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

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