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Literature summary for 1.13.11.34 extracted from

  • Zheng, M.; Zheng, M.; Ye, D.; Deng, Y.; Qiu, S.; Luo, X.; Chen, K.; Liu, H.; Jiang, H.
    Indole derivatives as potent inhibitors of 5-lipoxygenase: design, synthesis, biological evaluation, and molecular modeling (2007), Bioorg. Med. Chem. Lett., 17, 2414-2420.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole 82% inhibition at 0.005 mM Rattus norvegicus
1-(3,4-dichlorobenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole 38.5% inhibition at 0.005 mM Rattus norvegicus
1-(4-chlorophenoxy)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole 22% inhibition at 0.005 mM Rattus norvegicus
1-(4-chlorophenoxy)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole 26% inhibition at 0.005 mM Rattus norvegicus
1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 70% inhibition at 0.005 mM Rattus norvegicus
1-(4-methylbenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole 35% inhibition at 0.005 mM Rattus norvegicus
1-(4-methylbenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole 55% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole 41% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole 64% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-3-(4-morpholin-4-ylbutyl)-1H-indole 42% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole 95% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole 32% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-3-[3-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]propyl]-5-methoxy-2-methyl-1H-indole 46.5% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 80% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 54% inhibition at 0.005 mM Rattus norvegicus
1-benzyl-5-methoxy-2-methyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole 65% inhibition at 0.005 mM Rattus norvegicus
3-(2-morpholin-4-yl-2-oxoethyl)-1-phenoxy-1H-indole 21% inhibition at 0.005 mM Rattus norvegicus
3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole 16% inhibition at 0.005 mM Rattus norvegicus
3-(3-morpholin-4-yl-3-oxopropyl)-1-phenoxy-1H-indole 23% inhibition at 0.005 mM Rattus norvegicus
3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole 33% inhibition at 0.005 mM Rattus norvegicus
3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 62% inhibition at 0.005 mM Rattus norvegicus
3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole 64% inhibition at 0.005 mM Rattus norvegicus
4-((3,4-dichlorobenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one 27% inhibition at 0.005 mM Rattus norvegicus
4-((4-chlorobenzoyl)-1H-indol-3-yl)-1-morpholinobutan-1-one 32% inhibition at 0.005 mM Rattus norvegicus
4-(1-(4-methylbenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one 34% inhibition at 0.005 mM Rattus norvegicus
4-(1-benzoyl-1H-indol-3-yl)-1-morpholinobutan-1-one 58% inhibition at 0.005 mM Rattus norvegicus
4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one 26% inhibition at 0.005 mM Rattus norvegicus
5-chloro-1-(4-chlorophenoxy)-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 38% inhibition at 0.005 mM Rattus norvegicus
5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 71% inhibition at 0.005 mM Rattus norvegicus
5-methoxy-2-methyl-1-(4-methylbenzyl)-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 26% inhibition at 0.005 mM Rattus norvegicus
5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole 73% inhibition at 0.005 mM Rattus norvegicus
additional information inhibitor design, synthesis, biological evaluation, and molecular modeling, overview Rattus norvegicus
tert-butyl 4-[4-(1-benzyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate 38% inhibition at 0.005 mM Rattus norvegicus
tert-butyl 4-[4-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate 51.5% inhibition at 0.005 mM Rattus norvegicus
tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate 84% inhibition at 0.005 mM Rattus norvegicus
tert-butyl 4-[4-(5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate 71% inhibition at 0.005 mM Rattus norvegicus
ZD-2138
-
Rattus norvegicus
zileuton 87% inhibition at 0.005 mM Rattus norvegicus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate Rattus norvegicus
-
leukotriene A4 + H2O is unstable and metabolized to leukotriene B4 ?
arachidonic acid + O2 Rattus norvegicus
-
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
?
additional information Rattus norvegicus 5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes ?
-
?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus P12527
-
-

Source Tissue

Source Tissue Comment Organism Textmining
leukocyte peritoneal Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
Rattus norvegicus leukotriene A4 + H2O
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
Rattus norvegicus leukotriene A4 + H2O is unstable and metabolized to leukotriene B4 ?
arachidonic acid + O2
-
Rattus norvegicus (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
-
?
additional information 5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes Rattus norvegicus ?
-
?

Synonyms

Synonyms Comment Organism
5-lipoxygenase
-
Rattus norvegicus
5-LOX
-
Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00074
-
-
Rattus norvegicus tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
0.00083
-
-
Rattus norvegicus zileuton
0.00085
-
-
Rattus norvegicus 1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
0.00087
-
-
Rattus norvegicus 1-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
0.00095
-
-
Rattus norvegicus 1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
0.00133
-
-
Rattus norvegicus 5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
0.00206
-
-
Rattus norvegicus 3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
0.00225
-
-
Rattus norvegicus 1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
0.00238
-
-
Rattus norvegicus 3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
0.00316
-
-
Rattus norvegicus 5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
0.00317
-
-
Rattus norvegicus 1-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
0.074
-
-
Rattus norvegicus 4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one