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Literature summary for 3.4.21.21 extracted from

  • Parlow, J.J.; Dice, T.A.; Lachance, R.M.; Girard, T.J.; Stevens, A.M.; Stegeman, R.A.; Stallings, W.C.; Kurumbail, R.G.; South, M.S.
    Polymer-assisted solution-phase library synthesis and crystal structure of alpha-ketothiazoles as tissue factor VIIa inhibitors (2003), J. Med. Chem., 46, 4043-4049.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
3-methyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-pentanoic acid [4-guanidino-1-(thiazole-2-carbonyl)-butyl]-amide IC50: 300 nM, reversible, covalent Homo sapiens
3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00145 mM, reversible, covalent Homo sapiens
4,4-dimethyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-pentanoic acid [4-guanidino-1-(thiazole-2-carbonyl)-butyl]-amide IC50: 700 nM, reversible, covalent Homo sapiens
6-dimethylamino-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-hexanoic acid [4-guanidino-1-(thiazole-2-carbonyl)-butyl]-amide IC50: 0.00282 mM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(3,4,5-trifluoro-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 200 nM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(3-trifluoromethyl-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 800 nM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(4-iodo-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00156 mM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(4-nitro-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00588 mM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-hydroxy-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 110 nM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-m-tolyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 170 nM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-naphthalen-1-yl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.0056 mM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-naphthalen-2-yl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00195 mM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-o-tolyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 240 nM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-p-tolyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00129 mM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-phenyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 42 nM, reversible, covalent Homo sapiens
N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-pyridin-3-yl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 200 nM, reversible, covalent Homo sapiens
N-[2-(1-benzyl-1H-imidazol-4-yl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00997 mM, reversible, covalent Homo sapiens
N-[2-(2,6-dimethyl-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 700 nM, reversible, covalent Homo sapiens
N-[2-(2-fluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 90 nM, reversible, covalent Homo sapiens
N-[2-(3,4-difluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 160 nM, reversible, covalent Homo sapiens
N-[2-(3,5-difluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 190 nM, reversible, covalent Homo sapiens
N-[2-(3-chloro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 230 nM, reversible, covalent Homo sapiens
N-[2-(3-fluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 200 nM, reversible, covalent Homo sapiens
N-[2-(4-acetylamino-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 570 nM, reversible, covalent Homo sapiens
N-[2-(4-bromo-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 760 nM, reversible, covalent Homo sapiens
N-[2-(4-chloro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 680 mM, reversible, covalent Homo sapiens
N-[2-(4-cyano-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 340 nM, reversible, covalent Homo sapiens
N-[2-(4-fluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 170 nM, reversible, covalent Homo sapiens
N-[2-benzo[b]thiophen-3-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.0005 mM, reversible, covalent Homo sapiens
N-[2-benzyloxy-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00153 mM, reversible, covalent Homo sapiens
N-[2-biphenyl-3-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.00183 mM, reversible, covalent Homo sapiens
N-[2-biphenyl-4-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.0178 mM, reversible, covalent Homo sapiens
N-[2-cyclohexyl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 0.0033 mM, reversible, covalent Homo sapiens
N-[2-cyclopropyl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide IC50: 820 nM, reversible, covalent Homo sapiens
N-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-3-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-succinamic acid cyclohexyl ester IC50: 0.00318 mM, reversible, covalent Homo sapiens
N-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-4-methanesulfonyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-butyramide IC50: 0.0137 mM, reversible, covalent Homo sapiens
N-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-4-phenyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-butyramide IC50: 900 nM, reversible, covalent Homo sapiens
N1-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-succinamide IC50: 0.00103 mM, reversible, covalent Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
N-methylsulfonyl-D-Phe-Gly-Arg-p-nitroanilide + H2O
-
Homo sapiens N-methylsulfonyl-D-Phe-Gly-Arg + p-nitroaniline
-
?

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000042
-
IC50: 42 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-phenyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00009
-
IC50: 90 nM, reversible, covalent Homo sapiens N-[2-(2-fluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00011
-
IC50: 110 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-hydroxy-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00016
-
IC50: 160 nM, reversible, covalent Homo sapiens N-[2-(3,4-difluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00017
-
IC50: 170 nM, reversible, covalent Homo sapiens N-[2-(4-fluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00017
-
IC50: 170 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-m-tolyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00019
-
IC50: 190 nM, reversible, covalent Homo sapiens N-[2-(3,5-difluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0002
-
IC50: 200 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-pyridin-3-yl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0002
-
IC50: 200 nM, reversible, covalent Homo sapiens N-[2-(3-fluoro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0002
-
IC50: 200 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(3,4,5-trifluoro-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00023
-
IC50: 230 nM, reversible, covalent Homo sapiens N-[2-(3-chloro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00024
-
IC50: 240 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-o-tolyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0003
-
IC50: 300 nM, reversible, covalent Homo sapiens 3-methyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-pentanoic acid [4-guanidino-1-(thiazole-2-carbonyl)-butyl]-amide
0.00034
-
IC50: 340 nM, reversible, covalent Homo sapiens N-[2-(4-cyano-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0005
-
IC50: 0.0005 mM, reversible, covalent Homo sapiens N-[2-benzo[b]thiophen-3-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00057
-
IC50: 570 nM, reversible, covalent Homo sapiens N-[2-(4-acetylamino-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0007
-
IC50: 700 nM, reversible, covalent Homo sapiens 4,4-dimethyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-pentanoic acid [4-guanidino-1-(thiazole-2-carbonyl)-butyl]-amide
0.0007
-
IC50: 700 nM, reversible, covalent Homo sapiens N-[2-(2,6-dimethyl-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00076
-
IC50: 760 nM, reversible, covalent Homo sapiens N-[2-(4-bromo-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0008
-
IC50: 800 nM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(3-trifluoromethyl-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00082
-
IC50: 820 nM, reversible, covalent Homo sapiens N-[2-cyclopropyl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0009
-
IC50: 900 nM, reversible, covalent Homo sapiens N-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-4-phenyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-butyramide
0.00103
-
IC50: 0.00103 mM, reversible, covalent Homo sapiens N1-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-succinamide
0.00129
-
IC50: 0.00129 mM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-p-tolyl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00145
-
IC50: 0.00145 mM, reversible, covalent Homo sapiens 3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00153
-
IC50: 0.00153 mM, reversible, covalent Homo sapiens N-[2-benzyloxy-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00156
-
IC50: 0.00156 mM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(4-iodo-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00183
-
IC50: 0.00183 mM, reversible, covalent Homo sapiens N-[2-biphenyl-3-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00195
-
IC50: 0.00195 mM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-naphthalen-2-yl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00282
-
IC50: 0.00282 mM, reversible, covalent Homo sapiens 6-dimethylamino-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-hexanoic acid [4-guanidino-1-(thiazole-2-carbonyl)-butyl]-amide
0.00318
-
IC50: 0.00318 mM, reversible, covalent Homo sapiens N-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-3-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-succinamic acid cyclohexyl ester
0.0033
-
IC50: 0.0033 mM, reversible, covalent Homo sapiens N-[2-cyclohexyl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0056
-
IC50: 0.0056 mM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-naphthalen-1-yl-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00588
-
IC50: 0.00588 mM, reversible, covalent Homo sapiens N-[1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-2-(4-nitro-phenyl)-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.00997
-
IC50: 0.00997 mM, reversible, covalent Homo sapiens N-[2-(1-benzyl-1H-imidazol-4-yl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
0.0137
-
IC50: 0.0137 mM, reversible, covalent Homo sapiens N-[4-guanidino-1-(thiazole-2-carbonyl)-butyl]-4-methanesulfonyl-2-(3-phenyl-2-phenylmethanesulfonylamino-propionylamino)-butyramide
0.0178
-
IC50: 0.0178 mM, reversible, covalent Homo sapiens N-[2-biphenyl-4-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide
680
-
IC50: 680 mM, reversible, covalent Homo sapiens N-[2-(4-chloro-phenyl)-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl]-3-phenyl-2-phenylmethanesulfonylamino-propionamide