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20724-73-6 | Cytidine, 2'-C-methyl-
CAS No: 20724-73-6 Catalog No: AG002IX6 MDL No:MFCD02682947
Product Description
Catalog Number:
AG002IX6
Chemical Name:
Cytidine, 2'-C-methyl-
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 |
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