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 | UniProt | Comment | Textmining |
---|---|---|---|
Hepatovirus A | - |
HAV | - |
Human rhinovirus sp. | - |
HRV | - |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
dabcyl-GLRTQSND + H2O | fluorogenic peptide substrate | Hepatovirus A | ? | - |
? |
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 Maximum [°C] | Comment | Organism |
---|---|---|---|
37 | - |
assay at | Hepatovirus A |
37 | - |
assay at | Human rhinovirus sp. |
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 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 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 |