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Literature summary for 1.4.3.4 extracted from

  • Vilches-Herrera, M.; Miranda-Sepulveda, J.; Rebolledo-Fuentes, M.; Fierro, A.; Luehr, S.; Iturriaga-Vasquez, P.; Cassels, B.K.; Reyes-Parada, M.
    Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors (2009), Bioorg. Med. Chem., 17, 2452-2460.
    View publication on PubMed
Search for more literature for 1.4.3.4

Application

Application Comment Organism
drug development MAO-A is a target for a series of therapeutically valuable drugs. Thus, selective MAO-A inhibitors are used as antidepressants Rattus norvegicus
drug development MAO-B is a target for a series of therapeutically valuable drugs. Thus, selective MAO-B inhibitors are used in the treatment of Parkinson’s disease Rattus norvegicus
medicine MAO-A is a target for a series of therapeutically valuable drugs. Thus, selective MAO-A inhibitors are used as antidepressants Rattus norvegicus
medicine MAO-B is a target for a series of therapeutically valuable drugs. Thus, selective MAO-B inhibitorsare used in the treatment of Parkinson’s disease Rattus norvegicus

Inhibitors

Inhibitors Comment Organism Structure
(6-benzyloxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
(6-butoxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
(6-ethoxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
(6-methoxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
(6-methylthio-2-naphthyl)isopropylamine
-
 Rattus norvegicus
(6-propoxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
1-(1-naphthyl)-2-aminopropane
-
 Rattus norvegicus
1-(2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
1-(4-benzyloxyphenyl)-2-aminopropane
-
 Rattus norvegicus
1-(4-butoxyphenyl)-2-aminopropane
-
 Rattus norvegicus
1-(4-ethoxyphenyl)-2-aminopropane
-
 Rattus norvegicus
1-(4-methoxy-phenyl)-2-aminopropane
-
 Rattus norvegicus
1-(4-methylthiophenyl)-2-aminopropane
-
 Rattus norvegicus
1-(4-propoxyphenyl)-2-aminopropane
-
 Rattus norvegicus
1-phenyl-2-aminopropane
-
 Rattus norvegicus
additional information naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors of isozymes MAO-A and MAO-B, molecular docking, overview. Replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds results in increased electron-donating capacity and size of the aromatic moiety; naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors of isozymes MAO-B, molecular docking, overview. Replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds results in increased electron-donating capacity and size of the aromatic moiety. No inhibition of MAOB by N-4-methoxybenzyl-(4-methylthioamphetamine) hydrochloride, N-4-butoxybenzyl-(4-methylthioamphetamine) hydrochloride, and N-4-benzyloxybenzyl-(4-methylthioamphetamine) hydrochloride Rattus norvegicus
N-(4-benzyloxybenzyl)-4-methylthioamphetamine
-
 Rattus norvegicus
N-(4-butoxybenzyl)-4-methylthioamphetamine
-
 Rattus norvegicus
N-(4-hydroxybenzyl)-4-methylthioamphetamine weak inhibition of MAO-A; weak inhibition of MAO-B Rattus norvegicus
N-(4-methoxybenzyl)-4-methylthioamphetamine
-
 Rattus norvegicus
N-benzyl-(4-methylthioamphetamine) weak inhibition of MAO-A; weak inhibition of MAO-B Rattus norvegicus
N-benzyl-(6-butoxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus
N-benzyl-(6-methoxy-2-naphthyl)-2-aminopropane
-
 Rattus norvegicus

Organism

Organism UniProt Comment Textmining
Rattus norvegicus P19643 MAOB
-
Rattus norvegicus P21396 MAOA
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-dimethylaminophenethylamine + H2O + O2 substrate of MAO-B Rattus norvegicus ?
-
 ?
serotonin + H2O + O2 substrate of MAO-A Rattus norvegicus (5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
-
 ?

Synonyms

Synonyms Comment Organism
MAO-A
-
 Rattus norvegicus
MAO-B
-
 Rattus norvegicus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00013
-
 1-(4-propoxyphenyl)-2-aminopropane MAO-A Rattus norvegicus
0.00018
-
 (6-methoxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.00022
-
 1-(4-ethoxyphenyl)-2-aminopropane MAO-A Rattus norvegicus
0.00025
-
 1-(4-methoxy-phenyl)-2-aminopropane MAO-A Rattus norvegicus
0.00025
-
 1-(4-methylthiophenyl)-2-aminopropane MAO-A Rattus norvegicus
0.00032
-
 1-(4-butoxyphenyl)-2-aminopropane MAO-A Rattus norvegicus
0.00042
-
 1-(2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.00045
-
 (6-ethoxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.0005
-
 (6-methylthio-2-naphthyl)isopropylamine MAO-A Rattus norvegicus
0.00068
-
 (6-propoxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.00071
-
 1-(4-benzyloxyphenyl)-2-aminopropane MAO-B Rattus norvegicus
0.00153
-
 (6-butoxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.00256
-
 (6-benzyloxy-2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.00342
-
 1-(4-benzyloxyphenyl)-2-aminopropane MAO-A Rattus norvegicus
0.00378
-
 (6-benzyloxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.0056
-
 1-(1-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.00693
-
 N-benzyl-(6-methoxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.009
-
 N-(4-butoxybenzyl)-4-methylthioamphetamine MAO-A Rattus norvegicus
0.0122
-
 1-phenyl-2-aminopropane MAO-A Rattus norvegicus
0.0136
-
 (6-propoxy-2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.0145
-
 N-benzyl-(6-butoxy-2-naphthyl)-2-aminopropane MAO-A Rattus norvegicus
0.0163
-
 (6-ethoxy-2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.0222
-
 N-benzyl-(6-butoxy-2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.0247
-
 N-benzyl-(6-methoxy-2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.1
-
 N-benzyl-(4-methylthioamphetamine)
-
 Rattus norvegicus
0.1
-
 N-(4-hydroxybenzyl)-4-methylthioamphetamine
-
 Rattus norvegicus
0.1
-
 1-(4-ethoxyphenyl)-2-aminopropane above, MAO-B Rattus norvegicus
0.1
-
 1-(4-propoxyphenyl)-2-aminopropane above, MAO-B Rattus norvegicus
0.1
-
 1-(4-butoxyphenyl)-2-aminopropane above, MAO-B Rattus norvegicus
0.1
-
 N-(4-methoxybenzyl)-4-methylthioamphetamine MAO-A Rattus norvegicus
0.1
-
 N-(4-benzyloxybenzyl)-4-methylthioamphetamine MAO-A Rattus norvegicus
0.1
-
 1-(1-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.1
-
 1-(2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus
0.1
-
 (6-methoxy-2-naphthyl)-2-aminopropane MAO-B Rattus norvegicus