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Literature summary for 3.4.21.91 extracted from

  • Skorenski, M.; Milewska, A.; Pyrc, K.; Sienczyk, M.; Oleksyszyn, J.
    Phosphonate inhibitors of West Nile virus NS2B/NS3 protease (2019), J. Enzyme Inhib. Med. Chem., 34, 8-14 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.4.21.91

Application

Application Comment Organism
drug development the viral serine protease NS2B/NS3 is an attractive target for the development of anti-WNV agents West Nile virus

Inhibitors

Inhibitors Comment Organism Structure
Cbz-Lys-Arg-(4-GuPhe)P(OPh)2
-
 West Nile virus
Cbz-Lys-Arg-(4-GuPhg)P(OPh)2
-
 West Nile virus
Cbz-Lys-Arg-Arg
-
 West Nile virus
Cbz-Lys-Arg-ArgP(OPh)2
-
 West Nile virus
Cbz-Lys-Arg-LysP(OPh)2
-
 West Nile virus
diphenyl (1-[[(benzyloxy)carbonyl]amino]-3-carbamimidamidopropyl)phosphonate
-
 West Nile virus
diphenyl (1-[[(benzyloxy)carbonyl]amino]-4-carbamimidamidobutyl)phosphonate 12% inhibition West Nile virus
diphenyl (3-amino-1-[[(benzyloxy)carbonyl]amino]-3-oxopropyl)phosphonate 15% inhibition West Nile virus
diphenyl (3-amino-1-[[(benzyloxy)carbonyl]amino]propyl)phosphonate 12% inhibition West Nile virus
diphenyl (5-amino-1-[[(benzyloxy)carbonyl]amino]pentyl)phosphonate
-
 West Nile virus
diphenyl ([4-(1H-benzimidazol-1-yl)phenyl][[(benzyloxy)carbonyl]amino]methyl)phosphonate 4% inhibition West Nile virus
diphenyl ([[(benzyloxy)carbonyl]amino][4-(1H-pyrazol-1-yl)phenyl]methyl)phosphonate 5% inhibition West Nile virus
diphenyl ([[(benzyloxy)carbonyl]amino][4-(4-methylpiperazin-1-yl)phenyl]methyl)phosphonate 3% inhibition West Nile virus
diphenyl ([[(benzyloxy)carbonyl]amino][4-(morpholin-4-yl)phenyl]methyl)phosphonate 1% inhibition West Nile virus
diphenyl [(3-aminophenyl)[[(benzyloxy)carbonyl]amino]methyl]phosphonate 8% inhibition West Nile virus
diphenyl [(4-aminophenyl)[[(benzyloxy)carbonyl]amino]methyl]phosphonate 16% inhibition West Nile virus
diphenyl [1-[[(benzyloxy)carbonyl]amino]-3-(carbamimidoylsulfanyl)propyl]phosphonate 22% inhibition West Nile virus
diphenyl [2-(4-aminophenyl)-1-[[(benzyloxy)carbonyl]amino]ethyl]phosphonate 11% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](3-carbamimidamidophenyl)methyl]phosphonate 11% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](3-nitrophenyl)methyl]phosphonate 4% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](4-carbamimidamidophenyl)methyl]phosphonate
-
 West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](4-carbamimidoylphenyl)methyl]phosphonate 22% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](4-cyanophenyl)methyl]phosphonate 8% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](4-nitrophenyl)methyl]phosphonate 3% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](6-carbamimidoylnaphthalen-2-yl)methyl]phosphonate 12% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](6-cyanonaphthalen-2-yl)methyl]phosphonate 2% inhibition West Nile virus
diphenyl [[[(benzyloxy)carbonyl]amino](carbamimidamido)methyl]phosphonate
-
 West Nile virus
additional information development of a series of alpha-aminoalkylphosphonate diphenyl esters and their peptidyl derivatives as potent inhibitors of the NS2B/NS3 protease. Inhibitor synthesis and mechanism of serine proteases inhibition by alpha-aminoalkylphosphonate diphenyl esters involving the oxyanion hole, overview. Molecular docking West Nile virus
N2-(1,3-thiazol-2-yl)-L-arginyl-N-[(1S)-2-amino-2-oxo-1-(4-[[4-(trifluoromethyl)benzyl]oxy]phenyl)ethyl]-L-lysinamide
-
 West Nile virus
N2-(4-[(Z)-[3-(cyclohexylmethyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]benzoyl)-L-lysyl-N-[(1S)-2-amino-2-oxo-1-phenylethyl]-L-lysinamide
-
 West Nile virus
N2-(biphenyl-4-ylacetyl)-L-lysyl-L-Lys-L-Arg-aldehyde
-
 West Nile virus
N2-phenylacetyl-L-Lys-L-Lys-L-Arg-aldehyde
-
 West Nile virus
N2-[(3,4-dichlorophenyl)acetyl]-L-lysyl-N-[(1S)-1-(1-carbamimidoylpiperidin-4-yl)-2-oxoethyl]-L-lysinamide
-
 West Nile virus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.059
-
 Pyr-Arg-Thr-Lys-Arg-7-amido-4-methylcoumarin pH 8.5, 37°C West Nile virus

Organism

Organism UniProt Comment Textmining
West Nile virus
-
 WNV
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Pyr-Arg-Thr-Lys-Arg-7-amido-4-methylcoumarin + H2O
-
 West Nile virus Pyr-Arg-Thr-Lys-Arg + 7-amino-4-methylcoumarin
-
 ?

Synonyms

Synonyms Comment Organism
NS2B/NS3 protease
-
 West Nile virus
viral serine protease NS2B/NS3
-
 West Nile virus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at West Nile virus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8.5
-
 assay at West Nile virus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000006
-
 N2-(biphenyl-4-ylacetyl)-L-lysyl-L-Lys-L-Arg-aldehyde pH 8.5, 37°C West Nile virus
0.000009
-
 N2-phenylacetyl-L-Lys-L-Lys-L-Arg-aldehyde pH 8.5, 37°C West Nile virus
0.000039
-
 N2-(1,3-thiazol-2-yl)-L-arginyl-N-[(1S)-2-amino-2-oxo-1-(4-[[4-(trifluoromethyl)benzyl]oxy]phenyl)ethyl]-L-lysinamide pH 8.5, 37°C West Nile virus
0.00012
-
 Cbz-Lys-Arg-Arg pH 8.5, 37°C West Nile virus
0.00013
-
 N2-[(3,4-dichlorophenyl)acetyl]-L-lysyl-N-[(1S)-1-(1-carbamimidoylpiperidin-4-yl)-2-oxoethyl]-L-lysinamide pH 8.5, 37°C West Nile virus
0.0004
-
 Cbz-Lys-Arg-(4-GuPhe)P(OPh)2 pH 8.5, 37°C West Nile virus
0.0007
-
 Cbz-Lys-Arg-(4-GuPhg)P(OPh)2 pH 8.5, 37°C West Nile virus
0.00075
-
 N2-(4-[(Z)-[3-(cyclohexylmethyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]benzoyl)-L-lysyl-N-[(1S)-2-amino-2-oxo-1-phenylethyl]-L-lysinamide pH 8.5, 37°C West Nile virus
0.003
-
 Cbz-Lys-Arg-ArgP(OPh)2 pH 8.5, 37°C West Nile virus
0.004
-
 diphenyl [[[(benzyloxy)carbonyl]amino](carbamimidamido)methyl]phosphonate pH 8.5, 37°C West Nile virus
0.008
-
 Cbz-Lys-Arg-LysP(OPh)2 pH 8.5, 37°C West Nile virus
0.01
-
 diphenyl [[[(benzyloxy)carbonyl]amino](4-carbamimidamidophenyl)methyl]phosphonate pH 8.5, 37°C West Nile virus
0.013
-
 diphenyl (1-[[(benzyloxy)carbonyl]amino]-3-carbamimidamidopropyl)phosphonate pH 8.5, 37°C West Nile virus
0.022
-
 diphenyl (5-amino-1-[[(benzyloxy)carbonyl]amino]pentyl)phosphonate pH 8.5, 37°C West Nile virus