Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.4.22.28 extracted from

  • Kassem, A.F.; Batran, R.Z.; Abbas, E.M.H.; Elseginy, S.A.; Shaheen, M.N.F.; Elmahdy, E.M.
    New 4-phenylcoumarin derivatives as potent 3C protease inhibitors design, synthesis, anti-HAV effect and molecular modeling (2019), Eur. J. Med. Chem., 168, 447-460 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1-(2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)acetyl)-4-ethylthiosemicarbazide enzyme binding and protein interactions analysis Hepatovirus A
1-(2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)acetyl)-4-ethylthiosemicarbazide enzyme binding and protein interactions analysis Human rhinovirus sp.
1-(2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)acetyl)-4-methylthiosemicarbazide
-
Hepatovirus A
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-bromophenyl)ethylidene)acetohydrazide enzyme binding and protein interactions analysis Hepatovirus A
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-chlorophenyl)ethylidene)acetohydrazide enzyme binding and protein interactions analysis Hepatovirus A
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-chlorophenyl)ethylidene)acetohydrazide enzyme binding and protein interactions analysis Human rhinovirus sp.
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-phenylethylidene)acetohydrazide
-
Hepatovirus A
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-phenylethylidene)acetohydrazide enzyme binding and protein interactions analysis Human rhinovirus sp.
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(2-oxoindolin-3-ylidene)acetohydrazide
-
Hepatovirus A
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(5-bromo-2-oxoindolin-3-ylidene)acetohydrazide
-
Hepatovirus A
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(5-chloro-2-oxoindolin-3-ylidene)acetohydrazide
-
Hepatovirus A
2-[(2-oxo-4-phenyl-2H-chromen-7-yl)oxy]acetohydrazide
-
Hepatovirus A
4-phenyl-7-[(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)methoxy]-2H-chromen-2-one
-
Hepatovirus A
7-((4-ethyl-5-thioxo-1,2,4-triazol-3-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((4-methyl-5-thioxo-1,2,4-triazol-3-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((5-(2-(diethylamino)ethylthio)-1,3,4-oxadiazol-2-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((5-(2-(dimethylamino)ethylthio)-1,3,4-oxadiazol-2-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((5-(2-morpholinoethylthio)-1,3,4-oxadiazol-2-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((5-(2-morpholinoethylthio)-4-ethyl-4H-1,2,4-triazol-3-yl) methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((5-(ethylamino)-1,3,4-thiadiazol-2-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-((5-(methylamino)-1,3,4-thiadiazol-2-yl)methoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-(2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-oxoethoxy)-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-hydroxy-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
7-[(4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl)methoxy]-4-phenyl-2H-chromen-2-one
-
Hepatovirus A
acyclovir
-
Hepatovirus A
acyclovir
-
Human rhinovirus sp.
ethyl [(2-oxo-4-phenyl-2H-chromen-7-yl)oxy]acetate
-
Hepatovirus A
additional information a series of 4-phenylcoumarin derivatives is designed and synthesized starting from (2-oxo-4-phenyl-2H-chromen-7-yloxy) acetic acid hydrazide. Evaluation of the target compounds for their antiviral activity against hepatitis A virus reveals that 4-phenylcoumarin derivatives are potent 3C protease inhibitors, anti-HAV effect and molecular modeling, 3D-pharmacophore and quantitative structure activity relationship (QSAR) models, overview. The ethylthiosemicarbazide derivative is the most potent virucidal agent and the Schiff's bases cause the highest virustatic effects against viral adsorption and replication, respectively. Docking within the pocket site of HAV 3C protease (using the structure with PDB ID 2HAL) illustrates a strong H-profile with the key amino acids Gly170 and Cys172 similar to the co-crystallized ligand. Generation of pharmacophore and quantitative structure activity relationship (QSAR) models. Cytotoxicity and antiviral effect of the synthesized compounds on HAV 3C protease, detailed overview Hepatovirus A
additional information a series of 4-phenylcoumarin derivatives is designed and synthesized starting from (2-oxo-4-phenyl-2Hchromen-7-yloxy) acetic acid 2-[(2-oxo-4-phenyl-2H-chromen-7-yl)oxy]acetohydrazide. Evaluation of the target compounds for their antiviral activity against hepatitis A virus reveals that 4-phenylcoumarin derivatives are potent 3C protease inhibitors, anti-HRV effect and molecular modeling, 3D-pharmacophore and quantitative structure activity relationship (QSAR) models, overview. The ethylthiosemicarbazide derivative is the most potent virucidal agent and the Schiff's bases cause the highest virustatic effects against viral adsorption and replication, respectively. Generation of pharmacophore and quantitative structure activity relationship (QSAR) models Human rhinovirus sp.
N-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[(2-oxo-4-phenyl-2H-chromen-7-yl)oxy]acetamide
-
Hepatovirus A

Organism

Organism UniProt Comment Textmining
Hepatovirus A
-
HAV
-
Human rhinovirus sp.
-
HRV
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dabcyl-GLRTQSND + H2O fluorogenic peptide substrate Hepatovirus A ?
-
?

Synonyms

Synonyms Comment Organism
HAV 3C protease
-
Hepatovirus A
HAV 3Cpro
-
Hepatovirus A
HRV 3C protease
-
Human rhinovirus sp.
HRV 3Cpro
-
Human rhinovirus sp.
picornaviral 3C protease
-
Human rhinovirus sp.

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Hepatovirus A
37
-
assay at Human rhinovirus sp.

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Hepatovirus A
7.5
-
assay at Human rhinovirus sp.

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000104
-
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-chlorophenyl)ethylidene)acetohydrazide pH 7.5, 37°C Hepatovirus A
0.000217
-
2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-bromophenyl)ethylidene)acetohydrazide pH 7.5, 37°C Hepatovirus A
0.001903
-
1-(2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)acetyl)-4-ethylthiosemicarbazide pH 7.5, 37°C Hepatovirus A

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00413
-
pH 7.5, 37°C Human rhinovirus sp. 2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-phenylethylidene)acetohydrazide
0.00594
-
pH 7.5, 37°C Hepatovirus A 2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-chlorophenyl)ethylidene)acetohydrazide
0.0063
-
pH 7.5, 37°C Human rhinovirus sp. 2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-chlorophenyl)ethylidene)acetohydrazide
0.00719
-
pH 7.5, 37°C Hepatovirus A 2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)-N'-(1-(4-bromophenyl)ethylidene)acetohydrazide
0.0161
-
pH 7.5, 37°C Human rhinovirus sp. 1-(2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)acetyl)-4-ethylthiosemicarbazide
0.01778
-
pH 7.5, 37°C Hepatovirus A 1-(2-(2-oxo-4-phenyl-2H-chromen-7-yloxy)acetyl)-4-ethylthiosemicarbazide