PSI-6206

Names

[ Name ]:
PSI-6206

[Synonym ]:
2'-Deoxy-2'-fluoro-2'-methyluridine
PSI-6206
Uridine, 2'-deoxy-2'-fluoro-2'-methyl-
URI002
Ro-2433
2'-deoxy-2'-fluoro-2'-C-methyl-uridine
PSI6206

Biological Activity

[Description]:

PSI-6206 is the deaminated derivative of PSI-6130, which is a potent and selective inhibitor of HCV NS5B polymerase. PSI-6206 low potently inhibits HCV replicon with EC90 of >100 μM.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HCV

Research Areas >> Infection

[Target]

EC90：>100 μM (HCV replicon)[1]

[In Vitro]

PSI-6206 (RO2433) is tested for anti-HCV activity in both a cell-based quantitative real-time RT-PCR assay and surrogate bovine viral diarrhea virus (BVDV) assays. PSI-6206 demonstrates no activity or cytoxicity in any assay[1]. The formation of the 5′-triphosphate (TP) of PSI-6130 (PSI-6130-TP) and RO2433 (RO2433-TP) increases with time and reached steady state levels at 48 h. RO2433-TP also inhibits RNA synthesis by the native HCV replicase isolated from HCV replicon cells and the recombinant HCV polymerase NS5B[2]. PSI-6206 (RO2433) is the deaminated derivative of PSI-6130, which is a potent and selective inhibitor of HCV NS5B polymerase[3].

[References]

[1]. Clark JL, et al. Design, Synthesis, and Antiviral Activity of 2'-Deoxy-2'-fluoro-2'-C-methyl-cytidine, a Potent Inhibitor of Hepatitis C Virus Replication. J Med Chem. 2005 Aug 25;48(17):5504-8.

[2]. Ma H, et al. Characterization of the metabolic activation of hepatitis C virus nucleoside inhibitor beta-D-2'-Deoxy-2'-fluoro-2'-C-methylcytidine (PSI-6130) and identification of a novel active 5'-triphosphate species. J Biol Chem. 2007 Oct 12;282(41):29

[3]. Wang P, et al. An efficient and diastereoselective synthesis of PSI-6130: a clinically efficacious inhibitor of HCV NS5B polymerase. J Org Chem. 2009 Sep 4;74(17):6819-24.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Melting Point ]:
237-238℃

[ Molecular Formula ]:
C₁₀H₁₃FN₂O₅

[ Molecular Weight ]:
260.219

[ Exact Mass ]:
260.080841

[ PSA ]:
104.55000

[ LogP ]:
-0.77

[ Index of Refraction ]:
1.596

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%