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Literature summary for 7.1.1.8 extracted from
- Design, syntheses, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors (2011), Bioorg. Med. Chem., 19, 4608-4615.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 3-[(2,4-diethylphenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa |  |
| 3-[(2,6-diethylphenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[(2-bromo-4-fluorophenyl)amino]-5-(6-bromopyridin-3-yl)-5-methyl-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[(2-bromo-4-fluorophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[(4-bromophenyl)amino]-5-(6-bromopyridin-3-yl)-5-methyl-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[(4-bromophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[(4-chlorophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[(4-methoxyphenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 3-[[5-methyl-2,4-dioxo-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidin-3-yl]amino]benzoic acid | - |
Sus scrofa | |
| 4-[[5-(6-bromopyridin-3-yl)-5-methyl-2,4-dioxo-1,3-oxazolidin-3-yl]amino]benzonitrile | - |
Sus scrofa | |
| 4-[[5-methyl-2,4-dioxo-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidin-3-yl]amino]benzoic acid | - |
Sus scrofa | |
| 4-[[5-methyl-2,4-dioxo-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidin-3-yl]amino]benzonitrile | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-3-[(2,4-diethylphenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-3-[(2,6-diethylphenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-3-[(4-chlorophenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-3-[(4-methoxyphenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-5-methyl-3-(phenylamino)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-5-methyl-3-[(2-methyl-4-nitrophenyl)amino]-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-5-methyl-3-[(4-methylphenyl)amino]-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-(6-bromopyridin-3-yl)-5-methyl-3-[[4-(trifluoromethyl)phenyl]amino]-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-methyl-3-[(4-methylphenyl)amino]-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione | i.e. famoxadone, noncompetitive inhibitor with respect to the substrate of cytochrome c, but is a competitive inhibitor with respect to the substrate of decylubiquinol | Sus scrofa | |
| 5-methyl-5-(6-phenoxypyridin-3-yl)-3-[[4-(trifluoromethyl)phenyl]amino]-1,3-oxazolidine-2,4-dione | - |
Sus scrofa | |
| azoxystrobin | noncompetitive inhibitor with respect to the substrate of cytochrome c, but is a competitive inhibitor with respect to the substrate of decylubiquinol | Sus scrofa | |
| additional information | design, synthesis, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors, overview | Sus scrofa |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| quinol + 2 ferricytochrome c | Sus scrofa | - |
quinone + 2 ferrocytochrome c + 2 H+ | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Sus scrofa | - |
- |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| decylubiquinol + 2 ferricytochrome c | - |
Sus scrofa | decylubiquinone + 2 ferrocytochrome c + 2 H+ | - |
? | |
| quinol + 2 ferricytochrome c | - |
Sus scrofa | quinone + 2 ferrocytochrome c + 2 H+ | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| bc1 complex | - |
Sus scrofa |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 23 | - |
assay at | Sus scrofa |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.4 | - |
assay at | Sus scrofa |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.00000362 | - |
5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione | noncompetitive versus cytochrome c, pH 7.4, 23°C | Sus scrofa | |
| 0.00005143 | - |
5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione | competitive versus decylubiquinol, pH 7.4, 23°C | Sus scrofa | |
| 0.000329 | - |
3-[(4-bromophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | pH 7.4, 23°C | Sus scrofa | |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.00000944 | - |
pH 7.4, 23°C | Sus scrofa | 3-[(4-bromophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.00001593 | - |
pH 7.4, 23°C | Sus scrofa | 3-[(2,4-diethylphenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.00001879 | - |
pH 7.4, 23°C | Sus scrofa | 3-[(4-chlorophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.00002376 | - |
pH 7.4, 23°C | Sus scrofa | 5-methyl-3-[(4-methylphenyl)amino]-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.00002404 | - |
pH 7.4, 23°C | Sus scrofa | 3-[[5-methyl-2,4-dioxo-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidin-3-yl]amino]benzoic acid | |
| 0.0000482 | - |
in absence of n-dodecyl-beta-D-maltoside, pH 7.4, 23°C | Sus scrofa | 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione | |
| 0.00005792 | - |
pH 7.4, 23°C | Sus scrofa | 3-[(4-methoxyphenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.00005998 | - |
pH 7.4, 23°C | Sus scrofa | 3-[(2-bromo-4-fluorophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.00006326 | - |
pH 7.4, 23°C | Sus scrofa | 5-methyl-5-(6-phenoxypyridin-3-yl)-3-[[4-(trifluoromethyl)phenyl]amino]-1,3-oxazolidine-2,4-dione | |
| 0.000142 | - |
in presence of n-dodecyl-beta-D-maltoside, pH 7.4, 23°C | Sus scrofa | 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione | |
| 0.0002752 | - |
pH 7.4, 23°C | Sus scrofa | 4-[[5-methyl-2,4-dioxo-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidin-3-yl]amino]benzonitrile | |
| 0.000337 | - |
in absence of n-dodecyl-beta-D-maltoside, pH 7.4, 23°C | Sus scrofa | 3-[(4-bromophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.0004347 | - |
in absence of n-dodecyl-beta-D-maltoside, pH 7.4, 23°C | Sus scrofa | azoxystrobin | |
| 0.000527 | - |
in presence of n-dodecyl-beta-D-maltoside, pH 7.4, 23°C | Sus scrofa | azoxystrobin | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-5-methyl-3-(phenylamino)-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 3-[(2-bromo-4-fluorophenyl)amino]-5-(6-bromopyridin-3-yl)-5-methyl-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-3-[(2,6-diethylphenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 3-[(4-bromophenyl)amino]-5-(6-bromopyridin-3-yl)-5-methyl-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-5-methyl-3-[[4-(trifluoromethyl)phenyl]amino]-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 4-[[5-(6-bromopyridin-3-yl)-5-methyl-2,4-dioxo-1,3-oxazolidin-3-yl]amino]benzonitrile | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-5-methyl-3-[(4-methylphenyl)amino]-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-3-[(4-chlorophenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-3-[(4-methoxyphenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-3-[(2,4-diethylphenyl)amino]-5-methyl-1,3-oxazolidine-2,4-dione | |
| 0.001 | - |
above, pH 7.4, 23°C | Sus scrofa | 5-(6-bromopyridin-3-yl)-5-methyl-3-[(2-methyl-4-nitrophenyl)amino]-1,3-oxazolidine-2,4-dione | |
| 0.001049 | - |
in presence of n-dodecyl-beta-D-maltoside, pH 7.4, 23°C | Sus scrofa | 3-[(4-bromophenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.001517 | - |
pH 7.4, 23°C | Sus scrofa | 3-[(2,6-diethylphenyl)amino]-5-methyl-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidine-2,4-dione | |
| 0.005312 | - |
pH 7.4, 23°C | Sus scrofa | 4-[[5-methyl-2,4-dioxo-5-(6-phenoxypyridin-3-yl)-1,3-oxazolidin-3-yl]amino]benzoic acid | |
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