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ChemicalBook--->CAS DataBase List--->691852-58-1

691852-58-1

691852-58-1 Structure

691852-58-1 Structure
IdentificationBack Directory
[Name]

5-Cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-3-benzofurancarboxamide
[CAS]

691852-58-1
[Synonyms]

HCV 796
CS-1844
Nesbuvir
VB-19796)
nesbuvir = HCV-796
HCV-796 (Nesbuvir)
5-Cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-3-benzofurancarboxamide
3-Benzofurancarboxamide, 5-cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-
5-Cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-3-benzofurancarboxamide Nesbuvir HCV 796
[Molecular Formula]

C22H23FN2O5S
[MDL Number]

MFCD22208574
[MOL File]

691852-58-1.mol
[Molecular Weight]

446.49
Chemical PropertiesBack Directory
[density ]

1.407
[storage temp. ]

Store at -20°C
[solubility ]

≥22.3 mg/mL in DMSO; insoluble in H2O; ≥97.8 mg/mL in EtOH with gentle warming
[form ]

solid
[pka]

13.88±0.46(Predicted)
[color ]

White to off-white
Spectrum DetailBack Directory
[Spectrum Detail]

5-Cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-3-benzofurancarboxamide(691852-58-1)1HNMR
Hazard InformationBack Directory
[Biological Activity]

nesbuvir is a novel selective inhibitor of nonstructural protein 5b (ns5b) polymerase with ic50 value of 5 nm [1].ns5b (nonstructural protein 5b) is a viral protein found in hcv and plays an important role in hcv rna replicate by using the viral positive rna strand as its template and catalyzing the polymerization of rntp during rna replication. as the principal catalytic enzyme for hcv replication, ns5b is a viable target for hcv-rna replication and used as a target for hcv therapy [2] [3].nesbuvir is a selective ns5b polymerase inhibitor and has a different selectivity with the reported alk inhibitor crizotinib. when tested with huh7.5 cell line, nesbuvir showed the highest selectivity for ns5b and mutations reduced the cells susceptibility [1]. in clone a cells derived from huh-7 cells containing approximately 1,000 genome copies of hcv genotype 1b replicon per cell, nesbuvir treatment with the concentration of 0.1 and 1 μm for 16-day reduced about 3.6 log10 and 4.2 log10 hcv rna levels, respectively [2].in the chimeric mouse model, nesbuvir treatment resulted in a 2.02 +/- 0.55 log reduction in hcv titer, whereas in combination with interferon using a suboptimal dose of 30 mg/kg three times per day showed a 2.44 log reduction and were better than interferon treatment only [4].
[in vitro]

Replicon cells are treated with 1 mg/mL G418 and combinations of the two compounds. Nesbuvir (HCV-796) is added to 40 or 80 nM (approximately 10 and 20 times the EC 50 in a 3-day replicaon inhibition assay, respectively) and Boceprevir is added to 400 or 800 nM (approximately 2 and 4 times the EC 50 , respectively). The EC 50 s for Nesbuvir and Boceprevir for the parental replica in the transient expression assay are comparable to those obtained in the 3-day inhibition assay with the stable replicon cells; the EC 50 for Nesbuvir in the transient expression assay is 14 nM, whereas it is 5 nM for the stable replicon; and the EC 50 for Boceprevir in the transient expression assay is 608 nM, whereas it is 201 nM for the stable replicon.

[in vivo]

Among a huge variety of yet characterized nucleoside and non-nucleoside inhibitors (NNI), the benzofurane derivative NNI Nesbuvir (HCV-796) is demonstrated to yield significant antiviral effects in mice with chimeric human livers and in patients infected with HCV. HCV-796 binds to a hydrophobic binding pocket at the “palm” domain of NS5B; however, its mode of inhibition remains to be defined.

[target]

HCV NS5B RNA-dependent RNA polymerase
[References]

[1]. flint, m., et al., selection and characterization of hepatitis c virus replicons dually resistant to the polymerase and protease inhibitors hcv-796 and boceprevir (sch 503034). antimicrob agents chemother, 2009. 53(2): p. 401-11.
[2]. howe, a.y., et al., molecular mechanism of hepatitis c virus replicon variants with reduced susceptibility to a benzofuran inhibitor, hcv-796. antimicrob agents chemother, 2008. 52(9): p. 3327-38.
[3]. meshram, r.j. and r.n. gacche, effective epitope identification employing phylogenetic, mutational variability, sequence entropy, and correlated mutation analysis targeting ns5b protein of hepatitis c virus: from bioinformatics to therapeutics. j mol recognit, 2015.
[4]. kneteman, n.m., et al., hcv796: a selective nonstructural protein 5b polymerase inhibitor with potent anti-hepatitis c virus activity in vitro, in mice with chimeric human livers, and in humans infected with hepatitis c virus. hepatology, 2009. 49(3): p. 745-52.
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