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Literature summary for 3.4.21.98 extracted from

  • Johansson, P.O.; Baeck, M.; Kvarnstroem, I.; Jansson, K.; Vrang, L.; Hamelink, E.; Hallberg, A.; Rosenquist, A.; Samuelsson, B.
    Potent inhibitors of the hepatitis C virus NS3 protease: use of a novel P2 cyclopentane-derived template (2006), Bioorg. Med. Chem., 14, 5136-5151.
    View publication on PubMed
Search for more literature for 3.4.21.98

Application

Application Comment Organism
drug development series of hepatitis C virus NS3 protease inhibitors comprising a trisubstituted cyclopentane N-acyl-(4R)-hydroxyproline mimic in the P2 position. The frequently used P2 hydroxyproline scaffold can successfully be displaced by a properly substituted cyclopentane scaffold. Further refinements of the compounds may provide even more effective hepatitis C virus NS3 protease inhibitors Hepacivirus C

Inhibitors

Inhibitors Comment Organism Structure
(1R,2S)-1-[[(1R,2R,4S)-2-((S)-1-cyclopentylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
(1R,2S)-1-[[(1R,2R,4S)-2-((S)-1-tert-butylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
(1R,2S)-1-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyldimethylcarbamoyl-methyl)-carbamoyl]-2,2-dimethylpropylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
(1R,2S)-1-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexylmethylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
(1R,2S)-1-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexylmethylcarbamoyl-methyl)-methyl-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(R)-1-[((R)-cyclohexylmethoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-butyric acid 21% inhibition at a concentration of 10 micromol Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(R)-1-[((S)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid 35% inhibition at a concentration of 10 micromol Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((R)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid 37% inhibition at a concentration of 10 micromol Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-butyric acid 65% inhibition at a concentration of 10 micromol Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid 100% inhibition at a concentration of 10 micromol Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
(S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexylmethylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-4,4-difluoro-butyric acid
-
 Hepacivirus C

Organism

Organism UniProt Comment Textmining
Hepacivirus C
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Ac-Asp-Glu-Asp(EDANS)-Glu-Glu-Abu-psi-(COO)Ala-Ser-Lys(DABCYL)-NH2 + H2O
-
 Hepacivirus C ?
-
 ?

Synonyms

Synonyms Comment Organism
NS3 protease
-
 Hepacivirus C

Cofactor

Cofactor Comment Organism Structure
KKGSVVIVGRIVLSGK NS4A cofactor Hepacivirus C

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000016
-
 (1R,2S)-1-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyldimethylcarbamoyl-methyl)-carbamoyl]-2,2-dimethylpropylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
0.000022
-
 (1R,2S)-1-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexylmethylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
0.00056
-
 (S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexylmethylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-4,4-difluoro-butyric acid
-
 Hepacivirus C
0.0012
-
 (S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
0.0017
-
 (S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
0.0023
-
 (S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
0.0027
-
 (1R,2S)-1-[[(1R,2R,4S)-2-((S)-1-cyclopentylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
0.0066
-
 (S)-2-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-pentanoic acid
-
 Hepacivirus C
0.0069
-
 (1R,2S)-1-[[(1R,2R,4S)-2-((S)-1-tert-butylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C
0.01
-
 (1R,2S)-1-[[(1R,2R,4S)-2-[(S)-1-[((S)-cyclohexylmethylcarbamoyl-methyl)-methyl-carbamoyl]-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino]-2-vinyl-cyclopropanecarboxylic acid
-
 Hepacivirus C