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Literature summary for 3.4.21.98 extracted from

  • Shi, F.; Zhang, Y.; Xu, W.
    Discovery of a series of novel compounds with moderate anti-hepatitis C virus NS3 protease activity in vitro (2015), Bioorg. Med. Chem., 23, 5539-5545 .
    View publication on PubMed
Search for more literature for 3.4.21.98

Application

Application Comment Organism
drug development NS3 protease represents a drug target for treatment of HCV infections Hepatitis C virus genotype 1b

Inhibitors

Inhibitors Comment Organism Structure
(2S,4S)-1-((S)-2-(furan-2-carboxamido)-3,3-dimethylbutanoyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
-
 Hepatitis C virus genotype 1b
(2S,4S)-1-((S)-2-benzamido-2-cyclohexylacetyl)-N-((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
-
 Hepatitis C virus genotype 1b
(2S,4S)-1-((S)-2-benzamido-2-cyclohexylacetyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
-
 Hepatitis C virus genotype 1b
(2S,4S)-1-((S)-2-cyclohexyl-2-(thiophene-2-carboxamido)acetyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
-
 Hepatitis C virus genotype 1b
(2S,4S)-1-((S)-2-cyclohexyl-2-isobutyramidoacetyl)-N-((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
-
 Hepatitis C virus genotype 1b
(2S,4S)-1-((S)-2-isobutyramido-3-phenylpropanoyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
-
 Hepatitis C virus genotype 1b
benzyl((S)-1-cyclohexyl-2-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-2-oxoethyl)carbamate
-
 Hepatitis C virus genotype 1b
boceprevir
-
 Hepatitis C virus genotype 1b
additional information design and synthesis of a series of novel compounds by incorporating different amino acid residues in P1/P1' and P3/P3' position to develop antiviral agents. All designed compounds show moderate anti-HCV NS3 protease activity, detailed structure-activity relationship (SAR) analysis, overview Hepatitis C virus genotype 1b
N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4S)-4-(4-methoxybenzamido)-L-prolyl-N-(cyclopropanesulfonyl)-L-leucinamide
-
 Hepatitis C virus genotype 1b
N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4S)-4-[(naphthalene-2-carbonyl)amino]-L-prolyl-N-(cyclopropanesulfonyl)-L-leucinamide
-
 Hepatitis C virus genotype 1b
N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4S)-4-[2-(2,3-dimethylanilino)benzamido]-L-prolyl-N-(cyclopropanesulfonyl)-L-leucinamide
-
 Hepatitis C virus genotype 1b
telaprevir
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-1-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-1-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-1-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-4-methyl-1-oxopentan-2-yl)carbamate
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-1-((2S,4S)-2-(((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-1-cyclohexyl-2-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-2-oxoethyl)-carbamate
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-3,3-dimethyl-1-((2S,4S)-2-(((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)carbamate
-
 Hepatitis C virus genotype 1b
tert-butyl((S)-3-(1H-indol-3-yl)-1-((2S,4S)-2-(((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxopropan-2-yl)carbamate
-
 Hepatitis C virus genotype 1b

Organism

Organism UniProt Comment Textmining
Hepatitis C virus genotype 1b P26662 HCV, isolate Japanese
-

Synonyms

Synonyms Comment Organism
HCV NS3/4A protease
-
 Hepatitis C virus genotype 1b
hepatitis C virus NS3/4A protease
-
 Hepatitis C virus genotype 1b
NS3 protease
-
 Hepatitis C virus genotype 1b

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Hepatitis C virus genotype 1b

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000014
-
 boceprevir pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b
0.00004
-
 telaprevir pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00045
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b telaprevir
0.0019
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b (2S,4S)-1-((S)-2-cyclohexyl-2-(thiophene-2-carboxamido)acetyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
0.0021
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4S)-4-[2-(2,3-dimethylanilino)benzamido]-L-prolyl-N-(cyclopropanesulfonyl)-L-leucinamide
0.0025
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b (2S,4S)-1-((S)-2-benzamido-2-cyclohexylacetyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
0.0045
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b benzyl((S)-1-cyclohexyl-2-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-2-oxoethyl)carbamate
0.0056
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-3-(1H-indol-3-yl)-1-((2S,4S)-2-(((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxopropan-2-yl)carbamate
0.0059
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-1-((2S,4S)-2-(((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate
0.0071
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-1-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate
0.0074
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b (2S,4S)-1-((S)-2-benzamido-2-cyclohexylacetyl)-N-((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
0.034
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b (2S,4S)-1-((S)-2-(furan-2-carboxamido)-3,3-dimethylbutanoyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
0.072
-
 pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-1-cyclohexyl-2-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-2-oxoethyl)-carbamate
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b (2S,4S)-1-((S)-2-isobutyramido-3-phenylpropanoyl)-N-((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4S)-4-(4-methoxybenzamido)-L-prolyl-N-(cyclopropanesulfonyl)-L-leucinamide
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4S)-4-[(naphthalene-2-carbonyl)amino]-L-prolyl-N-(cyclopropanesulfonyl)-L-leucinamide
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-1-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-1-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-4-methyl-1-oxopentan-2-yl)carbamate
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b tert-butyl((S)-3,3-dimethyl-1-((2S,4S)-2-(((S)-4-methyl-1-(4-methylphenylsulfonamido)-1-oxopentan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)carbamate
0.1
-
 above, pH 7.5, temperature not specified in the publication Hepatitis C virus genotype 1b (2S,4S)-1-((S)-2-cyclohexyl-2-isobutyramidoacetyl)-N-((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide

General Information

General Information Comment Organism
additional information HCV is a member of the Flaviviridae family consisting of a positive single strand RNA that encodes a polyprotein. This polyprotein is cleaved to the structural and nonstructural (NS) proteins by both host and viral proteases.4 The NS3 region is a trypsin-like serine protease that plays an essential role in viral replication and involves in processes to attenuate and evade the host cell's natural immune defense Hepatitis C virus genotype 1b
physiological function the hepatitis C virus (HCV) NS3/4A protease that plays an important role in the viral life cycle Hepatitis C virus genotype 1b