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2'-C-Methylcytidine

CAS No.:
20724-73-6
Catalog Number:
AG002IX6
Molecular Formula:
C10H15N3O5
Molecular Weight:
257.2432
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
250mg
98%
In Stock USA
United States
$125
- +
1g
98%
In Stock USA
United States
$357
- +
5g
98%
In Stock USA
United States
$1225
- +
Product Description
Catalog Number:
AG002IX6
Chemical Name:
2'-C-Methylcytidine
CAS Number:
20724-73-6
Molecular Formula:
C10H15N3O5
Molecular Weight:
257.2432
MDL Number:
MFCD02682947
IUPAC Name:
4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one
InChI:
InChI=1S/C10H15N3O5/c1-10(17)7(15)5(4-14)18-8(10)13-3-2-6(11)12-9(13)16/h2-3,5,7-8,14-15,17H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,10-/m1/s1
InChI Key:
PPUDLEUZKVJXSZ-VPCXQMTMSA-N
SMILES:
OC[C@H]1O[C@H]([C@]([C@@H]1O)(C)O)n1ccc(nc1=O)N
UNII:
27FS20C1D8
Properties
Complexity:
424  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
257.101g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
257.246g/mol
Monoisotopic Mass:
257.101g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
129A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.4  
Literature
Title Journal
Nucleotide prodrugs of 2'-deoxy-2'-spirooxetane ribonucleosides as novel inhibitors of the HCV NS5B polymerase. Journal of medicinal chemistry 20140313
Inhibition of norovirus replication by the nucleoside analogue 2'-C-methylcytidine. Biochemical and biophysical research communications 20121102
Synthesis and characterization of 2'-C-Me branched C-nucleosides as HCV polymerase inhibitors. Bioorganic & medicinal chemistry letters 20120615
Anti-hepatitis C virus activity of 3-hydroxy caruilignan C from Swietenia macrophylla stems. Journal of viral hepatitis 20120501
Novel substituted 9-norbornylpurines and their activities against RNA viruses. Bioorganic & medicinal chemistry letters 20120301
Synthesis and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methyl-7-deazapurine nucleosides, their phosphoramidate prodrugs and 5'-triphosphates. Bioorganic & medicinal chemistry letters 20111201
Quinoline tricyclic derivatives. Design, synthesis and evaluation of the antiviral activity of three new classes of RNA-dependent RNA polymerase inhibitors. Bioorganic & medicinal chemistry 20111201
Synthesis and in vitro activity of novel N-3 acylated TSAO-T compounds against HIV-1 and HCV. European journal of medicinal chemistry 20111001
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. Bioorganic & medicinal chemistry letters 20110701
San-Huang-Xie-Xin-Tang extract suppresses hepatitis C virus replication and virus-induced cyclooxygenase-2 expression. Journal of viral hepatitis 20110701
Anti-hepatitis C virus activity of Acacia confusa extract via suppressing cyclooxygenase-2. Antiviral research 20110101
Antiviral drugs against hepatitis C virus. Genetic vaccines and therapy 20110101
2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase. Journal of medicinal chemistry 20101125
Efficacy of 2'-C-methylcytidine against yellow fever virus in cell culture and in a hamster model. Antiviral research 20100601
Enhancement of intestinal absorption of 2-methyl cytidine prodrugs. Drug delivery 20100501
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. Antiviral research 20100301
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. Journal of medicinal chemistry 20090910
Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine. European journal of medicinal chemistry 20090901
Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase. Bioorganic & medicinal chemistry letters 20090301
Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro. Journal of medicinal chemistry 20090108
The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors. Antimicrobial agents and chemotherapy 20080501
2'-deoxy-4'-azido nucleoside analogs are highly potent inhibitors of hepatitis C virus replication despite the lack of 2'-alpha-hydroxyl groups. The Journal of biological chemistry 20080125
Nitazoxanide, tizoxanide and other thiazolides are potent inhibitors of hepatitis B virus and hepatitis C virus replication. Antiviral research 20080101
Combinations of 2'-C-methylcytidine analogues with interferon-alpha2b and triple combination with ribavirin in the hepatitis C virus replicon system. Antiviral chemistry & chemotherapy 20080101
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479. Bioorganic & medicinal chemistry letters 20070501
2'-C-methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus. Antiviral research 20070301
2'-C-Methyl branched pyrimidine ribonucleoside analogues: potent inhibitors of RNA virus replication. Antiviral chemistry & chemotherapy 20070101
Synthesis and pharmacokinetics of valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. Journal of medicinal chemistry 20061102
Hemin potentiates the anti-hepatitis C virus activity of the antimalarial drug artemisinin. Biochemical and biophysical research communications 20060915
In vitro selected Con1 subgenomic replicons resistant to 2'-C-methyl-cytidine or to R1479 show lack of cross resistance. Virology 20060801
Synthesis of 3'-beta-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents. Organic & biomolecular chemistry 20060407
Nucleoside analog inhibitors of hepatitis C virus replication. Infectious disorders drug targets 20060301
The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture. The Journal of biological chemistry 20060217
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. Antiviral chemistry & chemotherapy 20060101
Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication. Journal of medicinal chemistry 20050825
Inhibitory effect of 2'-substituted nucleosides on hepatitis C virus replication correlates with metabolic properties in replicon cells. Antimicrobial agents and chemotherapy 20050501
Nm 283, an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. Nucleosides, nucleotides & nucleic acids 20050101
Properties