Any feedback?
Literature summary for 1.4.3.4 extracted from
- Discovery, biological evaluation, and structure-activity and -selectivity relationships of 6'-substituted (E)-2-(benzofuran-3(2H)-ylidene)-N-methylacetamides, a novel class of potent and selective monoamine oxidase inhibitors (2013), J. Med. Chem., 56, 2651-2664.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (-)-L-deprenyl | - |
Rattus norvegicus |  |
| (2E)-2-[6-[(3-chlorobenzyl)oxy]-1-benzofuran-3(2H)-ylidene]-N-methylacetamide | - |
Rattus norvegicus | |
| (3E)-3-[2-(ethylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | 1% inhibition of isoform MAO-B at 0.01 mM, 14% inhibition of isoform MAO-A at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(isopropylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | 4% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3,3,3-trifluoropropane-1-sulfonate | 5% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-cyanobenzenesulfonate | - |
Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-fluorobenzenesulfonate | 6% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-(methylsulfonyl)benzenesulfonate | 6%inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-acetylbenzenesulfonate | 13% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-cyanobenzenesulfonate | 6% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-methoxybenzenesulfonate | 5% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-nitrobenzenesulfonate | 10% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 5-chlorothiophene-2-sulfonate | 2% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl benzenesulfonate | - |
Rattus norvegicus | |
| (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3,3,3-trifluoropropane-1-sulfonate | - |
Rattus norvegicus | |
| (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-cyanobenzenesulfonate | - |
Rattus norvegicus | |
| (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-methoxybenzenesulfonate | 17% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl benzenesulfonate | 6% inhibition of isoform MAO-B at 0.01 mM | Rattus norvegicus | |
| (R)-N-(prop-2-yn-1-yl)-2,3-dihydro-1H-inden-1-amine | specific inhibitor of isoform MAO-B | Rattus norvegicus | |
| 2-[6-[(3-chlorobenzyl)oxy]-1-benzofuran-3-yl]-N-methylacetamide | - |
Rattus norvegicus | |
| 3-oxo-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| 3-[2-(ethylamino)-2-oxoethyl]-1-benzofuran-6-yl 3-chlorobenzenesulfonate | 17% inhibition of isoform MAO-A at 0.01 mM | Rattus norvegicus | |
| 3-[2-(methylamino)-2-oxoethyl]-1-benzofuran-6-yl 3-chlorobenzenesulfonate | 31% inhibition of isoform MAO-A at 0.01 mM | Rattus norvegicus | |
| 4-(aminomethyl)-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| 4-[(methylamino)carbonyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | 9% inhibition of isoform MAO-B at 0.01 mM, 8% inhibition of isoform MAO-A at 0.01 mM | Rattus norvegicus | |
| 4-[(methylamino)methyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| 4-[2-(methylamino)-2-oxoethyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | - |
Rattus norvegicus | |
| 7-[(3-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one | - |
Rattus norvegicus | |
| chlorgyline | specific inhibitor of isoform MAO-A | Rattus norvegicus | |
| Iproniazid | nonselective inhibitor | Rattus norvegicus | |
| ladostigil | nonselective inhibitor | Rattus norvegicus | |
| moclobemide | specific inhibitor of isoform MAO-A | Rattus norvegicus | |
| additional information | isoform MAO-B is not inhibited by (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl benzenesulfonate, (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate, (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-cyanobenzenesulfonate, (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-acetylbenzenesulfonate, (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-(methylsulfonyl)benzenesulfonate, (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-cyanobenzenesulfonate, (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-methoxybenzenesulfonate, (3E)-3-[2-(ethylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate, moclobemide, 3-oxo-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate, and 7-[(3-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one | Rattus norvegicus | |
| NW 1772 | specific inhibitor of isoform MAO-B | Rattus norvegicus | |
| selegilline | specific inhibitor of isoform MAO-B | Rattus norvegicus | |
| tranylcypromine | nonselective inhibitor | Rattus norvegicus | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| mitochondrion | outer mitochondrial membrane | Rattus norvegicus | 5739 | - |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Rattus norvegicus | - |
- |
- |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| brain | - |
Rattus norvegicus | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| kynuramine + H2O + O2 | - |
Rattus norvegicus | 3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2 | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| amine-oxygen oxidoreductase | - |
Rattus norvegicus |
| MAO-A | isoform | Rattus norvegicus |
| MAO-B | isoform | Rattus norvegicus |
| monoamine oxidase A | isoform | Rattus norvegicus |
| monoamine oxidase B | isoform | Rattus norvegicus |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| FAD | dependent on | Rattus norvegicus | |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.000007 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-methoxybenzenesulfonate | |
| 0.0000091 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3,3,3-trifluoropropane-1-sulfonate | |
| 0.0000098 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 5-chlorothiophene-2-sulfonate | |
| 0.000011 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-cyanobenzenesulfonate | |
| 0.000011 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3,3,3-trifluoropropane-1-sulfonate | |
| 0.000012 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-chlorobenzenesulfonate | |
| 0.000015 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | |
| 0.000016 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-methoxybenzenesulfonate | |
| 0.000019 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-cyanobenzenesulfonate | |
| 0.000019 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-(methylsulfonyl)benzenesulfonate | |
| 0.000024 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-7-methyl-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl benzenesulfonate | |
| 0.000029 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-acetylbenzenesulfonate | |
| 0.000034 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl benzenesulfonate | |
| 0.000036 | - |
isoform MAO-B, pH and temperature not specified in the publication | Rattus norvegicus | (2E)-2-[6-[(3-chlorobenzyl)oxy]-1-benzofuran-3(2H)-ylidene]-N-methylacetamide | |
| 0.000037 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-nitrobenzenesulfonate | |
| 0.000041 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | |
| 0.000041 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-fluorobenzenesulfonate | |
| 0.000045 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(methylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 4-cyanobenzenesulfonate | |
| 0.000111 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | 4-[2-(methylamino)-2-oxoethyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | |
| 0.000284 | - |
isoform MAO-B, pH and temperature not specified in the publication | Rattus norvegicus | 2-[6-[(3-chlorobenzyl)oxy]-1-benzofuran-3-yl]-N-methylacetamide | |
| 0.000409 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | 3-[2-(methylamino)-2-oxoethyl]-1-benzofuran-6-yl 3-chlorobenzenesulfonate | |
| 0.000427 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | 7-[(3-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one | |
| 0.000997 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | 4-(aminomethyl)-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | |
| 0.001 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | 2-[6-[(3-chlorobenzyl)oxy]-1-benzofuran-3-yl]-N-methylacetamide | |
| 0.0017 | - |
isoform MAO-B, pH and temperature not specified in the publication | Rattus norvegicus | 4-[(methylamino)methyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | |
| 0.0031 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (2E)-2-[6-[(3-chlorobenzyl)oxy]-1-benzofuran-3(2H)-ylidene]-N-methylacetamide | |
| 0.0033 | - |
isoform MAO-B, pH and temperature not specified in the publication | Rattus norvegicus | 4-(aminomethyl)-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | |
| 0.0042 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | (3E)-3-[2-(ethylamino)-2-oxoethylidene]-2,3-dihydro-1-benzofuran-6-yl 3-chlorobenzenesulfonate | |
| 0.0054 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | 4-[(methylamino)methyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | |
| 0.0083 | - |
isoform MAO-B, pH and temperature not specified in the publication | Rattus norvegicus | 4-[2-(methylamino)-2-oxoethyl]-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate | |
| 0.01 | - |
isoform MAO-A, pH and temperature not specified in the publication | Rattus norvegicus | moclobemide | |
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
Legal
Curated at
Member of
