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Literature summary for 3.4.21.7 extracted from

  • Xue, F.; Seto, C.T.
    Structure-activity studies of cyclic ketone inhibitors of the serine protease plasmin: design, synthesis, and biological activity (2006), Bioorg. Med. Chem., 14, 8467-8487.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(10S,13S)-10-(1H-indol-3-ylmethyl)-8,11-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-9,12-diazabicyclo[13.2.2]nonadeca-1(17),15,18-triene-13-carboxamide
-
synthetic construct
(12S,15S)-12-(1H-indol-3-ylmethyl)-10,13-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-11,14-diazabicyclo[15.2.2]henicosa-1(19),17,20-triene-15-carboxamide
-
synthetic construct
(9S,12S)-9-(1H-indol-3-ylmethyl)-7,10-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-8,11-diazabicyclo[12.2.2]octadeca-1(16),14,17-triene-12-carboxamide
-
synthetic construct
L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
additional information peptide inhibitors that incorporate 3-oxotetrahydrofuran and 3-oxotetrahydrothiophene 1,1-dioxide groups have the highest activities. For cyclopentanone-based inhibitors, incorporation of electron-withdrawing groups such as O and SO2 into the ring improves their activities. Alkylamino substituents, with an optimal spacer length of 6 carbon atoms, can be added to the inhibitors to bind in the S1 subsite. Incorporating conformationally constrained peptide segments into the inhibitors do not improve their activities synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1-glycyl-4-oxopyrrolidin-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclohexyl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclopentyl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobenzyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobutyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-tryptophanamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(5-aminopentyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(7-aminoheptyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-[(trans-4-aminocyclohexyl)methyl]-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
-
synthetic construct

Organism

Organism UniProt Comment Textmining
synthetic construct
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
D-Val-Leu-Lys-p-nitroanilide + H2O
-
synthetic construct D-Val-Leu-Lys + p-nitroaniline
-
?

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0057
-
one of the most effective inhibitors synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide
0.009
-
one of the most effective inhibitors synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.013
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide
0.019
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobenzyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.022
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.025
-
-
synthetic construct (12S,15S)-12-(1H-indol-3-ylmethyl)-10,13-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-11,14-diazabicyclo[15.2.2]henicosa-1(19),17,20-triene-15-carboxamide
0.03
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-tryptophanamide
0.051
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(7-aminoheptyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.054
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-[(trans-4-aminocyclohexyl)methyl]-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.062
-
-
synthetic construct (10S,13S)-10-(1H-indol-3-ylmethyl)-8,11-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-9,12-diazabicyclo[13.2.2]nonadeca-1(17),15,18-triene-13-carboxamide
0.1
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(5-aminopentyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.14
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobutyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
0.3
-
-
synthetic construct (9S,12S)-9-(1H-indol-3-ylmethyl)-7,10-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-8,11-diazabicyclo[12.2.2]octadeca-1(16),14,17-triene-12-carboxamide
0.35
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1-glycyl-4-oxopyrrolidin-3-yl)-L-phenylalaninamide
0.375
-
-
synthetic construct L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide
1
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclopentyl)-L-phenylalaninamide
1
-
-
synthetic construct N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclohexyl)-L-phenylalaninamide