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Literature summary for 3.4.23.16 extracted from

  • Vacca, J.P.
    Design of tight-binding inhibitors (1994), Methods Enzymol., 241, 311-334.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(1-Benzyl-3-benzylcarbamoyl-3,3-difluoro-2-oxo-propyl)-carbamic acid benzyl ester
-
Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(4-oxo-4H-chromene-2-carbonyl)-piperazine-2-carboxylic acid tert-butylamide IC50: 0.13 nM Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(naphthalen-2-yloxy)-pyrrolidine-2-carboxylic acid tert-butylamide IC50: 18 nM Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(quinoline-8-sulfonyl)-piperazine-2-carboxylic acid tert-butylamide IC50: 0.03 nM Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide IC50: 0.41 nM Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide IC50: 38 nM Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperidine-2-carboxylic acid tert-butylamide IC50: 80 nM Human immunodeficiency virus 1
1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-pyrrolidine-2-carboxylic acid tert-butylamide IC50: 350 nM Human immunodeficiency virus 1
3-tert-Butylcarbamoyl-4-[2-hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-1-carboxylic acid benzyl ester 0.35-0.37 nM Human immunodeficiency virus 1
4-Benzyl-1-[2-hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide IC50: 2.0 mM Human immunodeficiency virus 1
4-oxo-4H-chromene-2-carboxylic acid (1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide IC50: 0.1 nM Human immunodeficiency virus 1
JG365 9 nM Human immunodeficiency virus 1
L-704,486 IC50: 7.8 nM Human immunodeficiency virus 1
additional information design of tight-binding human immunodeficiency virus type 1 protease inhibitors Human immunodeficiency virus 1
morpholine-4-carboxylic acid (1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide IC50: 2.4 nM Human immunodeficiency virus 1
N-(1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-isonicotinamide IC50: 1.3 nM Human immunodeficiency virus 1
N-(1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-nicotinamide IC50: 0.8 nM Human immunodeficiency virus 1
N1-[1-Benzyl-3-(2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-methoxy-3-oxo-propyl]-2-[2-(naphthalen-1-yloxy)-acetylamino]-succinamide
-
Human immunodeficiency virus 1
pyridine-2-carboxylic acid (1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide IC50: 4.6 nM Human immunodeficiency virus 1
[1-(1-Benzyl-3-benzylcarbamoyl-3,3-difluoro-2-oxo-propylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester
-
Human immunodeficiency virus 1
[1-(1-{1-benzyl-3-[2-(1-tert-butylcarbamoyl-2-methyl-butylcarbamoyl)-pyrrolidin-1-yl]-2-methoxy-propylcarbamoyl}-2-carbamoyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester IC50: 750 nM Human immunodeficiency virus 1
[1-Benzyl-2-hydroxy-4-(3-hydroxy-indan-1-ylcarbamoyl)-7-phenyl-hept-6-enyl]-carbamic acid tert-butyl ester IC50: 0.55 nM Human immunodeficiency virus 1
[1-Benzyl-3-(3-benzyl-1-isothiochroman-4-yl-2-oxo-pyrrolidin-3-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester IC50: 111 nM Human immunodeficiency virus 1
[1-Benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propyl]-carbamic acid tert-butyl ester IC50: 17 nM Human immunodeficiency virus 1
[1-Benzyl-4-(2,2-dioxo-2lambda6-isothiochroman-4-ylcarbamoyl)-2-hydroxy-7-phenyl-hept-6-enyl]-carbamic acid tert-butyl ester IC50: 2.3 nM Human immunodeficiency virus 1
{1-benzyl-3-[3-benzyl-1-(2,2-dioxo-2l6-isothiochroman-4-yl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester IC50: 14 nM Human immunodeficiency virus 1
{1-benzyl-3-[3-benzyl-1-(2-hydroxy-indan-1-yl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 37 nM Human immunodeficiency virus 1
{1-[1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-methoxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester IC50: 18 nM Human immunodeficiency virus 1
{1-[1-benzyl-3-(2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-methoxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester IC50: 210 nM Human immunodeficiency virus 1

Organism

Organism UniProt Comment Textmining
Human immunodeficiency virus 1
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information the cleavage site involves a Phe or Tyr as the N-terminal P1 side and a Pro as the C-terminal P1' side of the scissile bond Human immunodeficiency virus 1 ?
-
?

Subunits

Subunits Comment Organism
dimer
-
Human immunodeficiency virus 1

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00000058
-
N1-[1-Benzyl-3-(2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-methoxy-3-oxo-propyl]-2-[2-(naphthalen-1-yloxy)-acetylamino]-succinamide
-
Human immunodeficiency virus 1
0.00000066
-
JG365
-
Human immunodeficiency virus 1
0.000001
-
[1-(1-Benzyl-3-benzylcarbamoyl-3,3-difluoro-2-oxo-propylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester
-
Human immunodeficiency virus 1
0.0000023
-
3-[3-[2-[2-(isoquinolin-5-yloxy)-acetylamino]-3-methylsulfanyl-propionylamino]-2-methoxy-4-phenyl-butyryl]-5,5-dimethyl-thiazolidine-4-carboxylic acid tert-butylamide
-
Human immunodeficiency virus 1
0.0006
-
(1-Benzyl-3-benzylcarbamoyl-3,3-difluoro-2-oxo-propyl)-carbamic acid benzyl ester
-
Human immunodeficiency virus 1

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00000003
-
IC50: 0.03 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(quinoline-8-sulfonyl)-piperazine-2-carboxylic acid tert-butylamide
0.0000001
-
IC50: 0.1 nM Human immunodeficiency virus 1 4-oxo-4H-chromene-2-carboxylic acid (1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide
0.00000013
-
IC50: 0.13 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(4-oxo-4H-chromene-2-carbonyl)-piperazine-2-carboxylic acid tert-butylamide
0.00000041
-
IC50: 0.41 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide
0.00000055
-
IC50: 0.55 nM Human immunodeficiency virus 1 [1-Benzyl-2-hydroxy-4-(3-hydroxy-indan-1-ylcarbamoyl)-7-phenyl-hept-6-enyl]-carbamic acid tert-butyl ester
0.0000008
-
IC50: 0.8 nM Human immunodeficiency virus 1 N-(1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-nicotinamide
0.0000013
-
IC50: 1.3 nM Human immunodeficiency virus 1 N-(1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-isonicotinamide
0.0000023
-
IC50: 2.3 nM Human immunodeficiency virus 1 [1-Benzyl-4-(2,2-dioxo-2lambda6-isothiochroman-4-ylcarbamoyl)-2-hydroxy-7-phenyl-hept-6-enyl]-carbamic acid tert-butyl ester
0.0000024
-
IC50: 2.4 nM Human immunodeficiency virus 1 morpholine-4-carboxylic acid (1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide
0.0000046
-
IC50: 4.6 nM Human immunodeficiency virus 1 pyridine-2-carboxylic acid (1-{1-benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propylcarbamoyl}-2-methyl-propyl)-amide
0.0000078
-
IC50: 7.8 nM Human immunodeficiency virus 1 L-704,486
0.000014
-
IC50: 14 nM Human immunodeficiency virus 1 {1-benzyl-3-[3-benzyl-1-(2,2-dioxo-2l6-isothiochroman-4-yl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propyl}-carbamic acid tert-butyl ester
0.000017
-
IC50: 17 nM Human immunodeficiency virus 1 [1-Benzyl-3-[3-benzyl-1-(2-hydroxy-5-methyl-cyclopentyl)-2-oxo-pyrrolidin-3-yl]-2-hydroxy-propyl]-carbamic acid tert-butyl ester
0.000018
-
IC50: 18 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(naphthalen-2-yloxy)-pyrrolidine-2-carboxylic acid tert-butylamide
0.000018
-
IC50: 18 nM Human immunodeficiency virus 1 {1-[1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-methoxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester
0.000038
-
IC50: 38 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide
0.00008
-
IC50: 80 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperidine-2-carboxylic acid tert-butylamide
0.000111
-
IC50: 111 nM Human immunodeficiency virus 1 [1-Benzyl-3-(3-benzyl-1-isothiochroman-4-yl-2-oxo-pyrrolidin-3-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester
0.00021
-
IC50: 210 nM Human immunodeficiency virus 1 {1-[1-benzyl-3-(2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-methoxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester
0.00035
-
IC50: 350 nM Human immunodeficiency virus 1 1-[2-Hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-pyrrolidine-2-carboxylic acid tert-butylamide
0.00075
-
IC50: 750 nM Human immunodeficiency virus 1 [1-(1-{1-benzyl-3-[2-(1-tert-butylcarbamoyl-2-methyl-butylcarbamoyl)-pyrrolidin-1-yl]-2-methoxy-propylcarbamoyl}-2-carbamoyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
2
-
IC50: 2.0 mM Human immunodeficiency virus 1 4-Benzyl-1-[2-hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide