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Literature summary for 1.4.3.4 extracted from

  • Prins, L.H.; Petzer, J.P.; Malan, S.F.
    Inhibition of monoamine oxidase by indole and benzofuran derivatives (2010), Eur. J. Med. Chem., 45, 4458-4466.
    View publication on PubMed

Application

Application Comment Organism
drug development indole and benzofuran derivatives are promising reversible MAO-B inhibitors with a possible role in the treatment of neurodegenerative diseases such as Parkinson’s disease Homo sapiens
medicine monoamine oxidase is an important drug target for the treatment of neurological disorders Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
expression of MAO-A and MAO-B in baculovirus infected BTI insect cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2E)-3-(3-chlorophenyl)-N-(2-methyl-1H-indol-5-yl)prop-2-enamide
-
Homo sapiens
(2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide
-
Homo sapiens
(E)-3-chlorocinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
Homo sapiens
(E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
Homo sapiens
(R)-deprenyl i.e. selegiline, a MAO-B inhibitor Homo sapiens
1-methyl-N-(2-methyl-1H-indol-5-yl)-1lambda4-pyridine-3-carboxamide
-
Homo sapiens
3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide
-
Homo sapiens
3-chloro-N-(2-methyl-1H-indol-5-yl)benzamide
-
Homo sapiens
3-chlorobenzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
Homo sapiens
3-[(2-methyl-1H-indol-5-yl)carbamoyl]benzene-1-sulfonic acid
-
Homo sapiens
benzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
-
Homo sapiens
additional information design and synthesis of a series of indole and benzofuran derivatives, and evaluation as reversible inhibitors of the two MAO isozymes MAO-A and MAO-B, most compounds are selective MAO-B inhibitors, ligand docking study, overview Homo sapiens
N-(2-methyl-1H-indol-5-yl)benzamide
-
Homo sapiens
N-(2-methyl-1H-indol-5-yl)cyclohexanecarboxamide
-
Homo sapiens
rasagiline i.e. AGN 1135 Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P27338
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
kynuramine + O2
-
Homo sapiens 4-hydroxyquinoline + NH3 + H2O2
-
?

Synonyms

Synonyms Comment Organism
MAO
-
Homo sapiens
MAO-A
-
Homo sapiens
MAO-B
-
Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00003
-
3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide pH 7.4, 37°C, MAO-B Homo sapiens
0.00019
-
(E)-3-chlorocinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-B Homo sapiens
0.00033
-
3-chloro-N-(2-methyl-1H-indol-5-yl)benzamide pH 7.4, 37°C, MAO-B Homo sapiens
0.00043
-
3-chlorobenzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-B Homo sapiens
0.00052
-
(E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-B Homo sapiens
0.001
-
(E)-3-chlorocinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-A Homo sapiens
0.00165
-
N-(2-methyl-1H-indol-5-yl)benzamide pH 7.4, 37°C, MAO-B Homo sapiens
0.002
-
(2E)-3-(3-chlorophenyl)-N-(2-methyl-1H-indol-5-yl)prop-2-enamide pH 7.4, 37°C, MAO-A Homo sapiens
0.002
-
3-chlorobenzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-A Homo sapiens
0.0026
-
3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide pH 7.4, 37°C, MAO-A Homo sapiens
0.003
-
N-(2-methyl-1H-indol-5-yl)cyclohexanecarboxamide pH 7.4, 37°C, MAO-B Homo sapiens
0.00305
-
benzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-A Homo sapiens
0.0033
-
(E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-A Homo sapiens
0.00383
-
benzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester pH 7.4, 37°C, MAO-B Homo sapiens
0.00423
-
(2E)-3-(3-chlorophenyl)-N-(2-methyl-1H-indol-5-yl)prop-2-enamide pH 7.4, 37°C, MAO-B Homo sapiens
0.0055
-
1-methyl-N-(2-methyl-1H-indol-5-yl)-1lambda4-pyridine-3-carboxamide pH 7.4, 37°C, MAO-A Homo sapiens
0.00801
-
(2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide pH 7.4, 37°C, MAO-B Homo sapiens
0.0082
-
3-chloro-N-(2-methyl-1H-indol-5-yl)benzamide pH 7.4, 37°C, MAO-A Homo sapiens
0.0183
-
N-(2-methyl-1H-indol-5-yl)cyclohexanecarboxamide pH 7.4, 37°C, MAO-A Homo sapiens
0.0395
-
N-(2-methyl-1H-indol-5-yl)benzamide pH 7.4, 37°C, MAO-A Homo sapiens
0.0399
-
1-methyl-N-(2-methyl-1H-indol-5-yl)-1lambda4-pyridine-3-carboxamide pH 7.4, 37°C, MAO-B Homo sapiens
0.0683
-
3-[(2-methyl-1H-indol-5-yl)carbamoyl]benzene-1-sulfonic acid pH 7.4, 37°C, MAO-A Homo sapiens
0.0757
-
3-[(2-methyl-1H-indol-5-yl)carbamoyl]benzene-1-sulfonic acid pH 7.4, 37°C, MAO-B Homo sapiens
0.175
-
(2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide pH 7.4, 37°C, MAO-A Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00006
-
pH 7.4, 37°C, MAO-B Homo sapiens 3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide
0.00044
-
pH 7.4, 37°C, MAO-B Homo sapiens (E)-3-chlorocinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.00076
-
pH 7.4, 37°C, MAO-B Homo sapiens 3-chloro-N-(2-methyl-1H-indol-5-yl)benzamide
0.00099
-
pH 7.4, 37°C, MAO-B Homo sapiens 3-chlorobenzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.0012
-
pH 7.4, 37°C, MAO-B Homo sapiens (E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.00384
-
pH 7.4, 37°C, MAO-B Homo sapiens N-(2-methyl-1H-indol-5-yl)benzamide
0.0039
-
pH 7.4, 37°C, MAO-A Homo sapiens (E)-3-chlorocinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.00696
-
pH 7.4, 37°C, MAO-B Homo sapiens N-(2-methyl-1H-indol-5-yl)cyclohexanecarboxamide
0.0077
-
pH 7.4, 37°C, MAO-A Homo sapiens (2E)-3-(3-chlorophenyl)-N-(2-methyl-1H-indol-5-yl)prop-2-enamide
0.0077
-
pH 7.4, 37°C, MAO-A Homo sapiens 3-chlorobenzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.00889
-
pH 7.4, 37°C, MAO-B Homo sapiens benzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.0098
-
pH 7.4, 37°C, MAO-A Homo sapiens 3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide
0.00983
-
pH 7.4, 37°C, MAO-B Homo sapiens (2E)-3-(3-chlorophenyl)-N-(2-methyl-1H-indol-5-yl)prop-2-enamide
0.0116
-
pH 7.4, 37°C, MAO-A Homo sapiens benzoic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.0125
-
pH 7.4, 37°C, MAO-A Homo sapiens (E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
0.01882
-
pH 7.4, 37°C, MAO-B Homo sapiens (2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide
0.0208
-
pH 7.4, 37°C, MAO-A Homo sapiens 1-methyl-N-(2-methyl-1H-indol-5-yl)-1lambda4-pyridine-3-carboxamide
0.031
-
pH 7.4, 37°C, MAO-A Homo sapiens 3-chloro-N-(2-methyl-1H-indol-5-yl)benzamide
0.0694
-
pH 7.4, 37°C, MAO-A Homo sapiens N-(2-methyl-1H-indol-5-yl)cyclohexanecarboxamide
0.0926
-
pH 7.4, 37°C, MAO-B Homo sapiens 1-methyl-N-(2-methyl-1H-indol-5-yl)-1lambda4-pyridine-3-carboxamide
0.15
-
pH 7.4, 37°C, MAO-A Homo sapiens N-(2-methyl-1H-indol-5-yl)benzamide
0.1759
-
pH 7.4, 37°C, MAO-B Homo sapiens 3-[(2-methyl-1H-indol-5-yl)carbamoyl]benzene-1-sulfonic acid
0.259
-
pH 7.4, 37°C, MAO-A Homo sapiens 3-[(2-methyl-1H-indol-5-yl)carbamoyl]benzene-1-sulfonic acid
0.663
-
pH 7.4, 37°C, MAO-A Homo sapiens (2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide