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478182-28-4,MFCD03086098
Catalog No.:AA00DE0G

478182-28-4 | 4'-Azidocytidine

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Purity
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10mg
≥99%
in stock  
$1,118.00   $783.00
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50mg
≥99%
in stock  
$3,240.00   $2,268.00
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DE0G
Chemical Name:
4'-Azidocytidine
CAS Number:
478182-28-4
Molecular Formula:
C9H12N6O5
Molecular Weight:
284.2288
MDL Number:
MFCD03086098
SMILES:
[N-]=[N+]=N[C@]1(CO)O[C@H]([C@@H]([C@@H]1O)O)n1ccc(nc1=O)N
Properties
Computed Properties
 
Complexity:
529  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
Undefined Bond Stereocenter Count:
1  
XLogP3:
-1.8  

Literature

Title: Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug.

Journal: Antimicrobial agents and chemotherapy 20140401

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: PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.

Journal: Antimicrobial agents and chemotherapy 20100801

Title: Studies on the anti-hepatitis C virus activity of newly synthesized tropolone derivatives: identification of NS3 helicase inhibitors that specifically inhibit subgenomic HCV replication.

Journal: Bioorganic & medicinal chemistry 20100715

Title: Synthesis of new acridone derivatives, inhibitors of NS3 helicase, which efficiently and specifically inhibit subgenomic HCV replication.

Journal: Journal of medicinal chemistry 20100422

Title: Chemical stability of 4'-azidocytidine and its prodrug balapiravir.

Journal: Drug development and industrial pharmacy 20100401

Title: The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479).

Journal: Bioorganic & medicinal chemistry letters 20090801

Title: The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.

Journal: Journal of medicinal chemistry 20090514

Title: Substituted imidazopyridines as potent inhibitors of HCV replication.

Journal: Journal of hepatology 20090501

Title: Amidinoanthracyclines - a new group of potential anti-hepatitis C virus compounds.

Journal: Biological chemistry 20090401

Title: The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine.

Journal: Journal of medicinal chemistry 20090108

Title: 1,5-benzodiazepines, a novel class of hepatitis C virus polymerase nonnucleoside inhibitors.

Journal: Antimicrobial agents and chemotherapy 20081201

Title: New acridone-4-carboxylic acid derivatives as potential inhibitors of hepatitis C virus infection.

Journal: Bioorganic & medicinal chemistry 20081001

Title: Robust antiviral activity of R1626, a novel nucleoside analog: a randomized, placebo-controlled study in patients with chronic hepatitis C.

Journal: Hepatology (Baltimore, Md.) 20080801

Title: R1626 plus peginterferon Alfa-2a provides potent suppression of hepatitis C virus RNA and significant antiviral synergy in combination with ribavirin.

Journal: Hepatology (Baltimore, Md.) 20080801

Title: Physicochemical properties of the nucleoside prodrug R1626 leading to high oral bioavailability.

Journal: Drug development and industrial pharmacy 20080701

Title: Existence of hepatitis C virus NS5B variants naturally resistant to non-nucleoside, but not to nucleoside, polymerase inhibitors among untreated patients.

Journal: The Journal of antimicrobial chemotherapy 20080601

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: Future treatment options for HCV: double, triple, what is the optimal combination?

Journal: Best practice & research. Clinical gastroenterology 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: Specific targeted antiviral therapy for hepatitis C.

Journal: Current gastroenterology reports 20070301

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: 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: Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.

Journal: Journal of medicinal chemistry 19920417

Title: Klumpp K, et al. The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture. J Biol Chem. 2006 Feb 17;281(7):3793-9.

Title: Smith DB, et al. Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479. Bioorg Med Chem Lett. 2007 May 1;17(9):2570-6.

Title: Nguyen NM, et al. A randomized, double-blind placebo controlled trial of balapiravir, a polymerase inhibitor, in adult dengue patients. J Infect Dis. 2013 May 1;207(9):1442-1450.

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