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Literature summary for 1.13.11.34 extracted from

  • Karg, E.M.; Luderer, S.; Pergola, C.; Buehring, U.; Rossi, A.; Northoff, H.; Sautebin, L.; Troschuetz, R.; Werz, O.
    Structural optimization and biological evaluation of 2-substituted 5-hydroxyindole-3-carboxylates as potent inhibitors of human 5-lipoxygenase (2009), J. Med. Chem., 52, 3474-3483.
    View publication on PubMed

Application

Application Comment Organism
drug development due to their high potency against 5-lipoxygenase and the marked efficacy in biological systems, benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics Homo sapiens
drug development due to their high potency against 5-lipoxygenase and the marked efficacy in biological systems, benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics Rattus norvegicus

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate prevents leukotriene B4 production in pleural exudates of carrageenan-treated rats, associated with reduced severity of pleurisy. Significantly reduces the inflammatory reaction measured as exudate volume (77%), inflammatory cell numbers (40%), and leukotriene B4 levels (49%) in the pleural exudates Rattus norvegicus
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
-
Homo sapiens
ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
-
Homo sapiens
ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-(allylamino)-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-(benzylamino)-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-(diallylamino)-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
-
Homo sapiens
methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
-
Homo sapiens
N-(3-phenoxycinnamyl)-acetohydroxamic acid
-
Homo sapiens
zileuton
-
Homo sapiens
zileuton reduces exudate formation (77%), cell infiltration (41%), and leukotriene B4 exudate levels (66%) Rattus norvegicus

Metals/Ions

Metals/Ions Comment Organism Structure
Ca2+ stimulation with calcium ionophore Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Rattus norvegicus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
blood
-
Homo sapiens
-
neutrophil
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
arachidonate + O2
-
Homo sapiens (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
?

Synonyms

Synonyms Comment Organism
5-lipoxygenase
-
Homo sapiens
5-lipoxygenase
-
Rattus norvegicus
5-LO
-
Homo sapiens
5-LO
-
Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000031
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000038
-
recombinant 5-lipoxygenase Homo sapiens N-(3-phenoxycinnamyl)-acetohydroxamic acid
0.000045
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000049
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000067
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000084
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000086
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000095
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000096
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.000097
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00013
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00013
-
recombinant 5-lipoxygenase Homo sapiens ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
0.00013
-
recombinant 5-lipoxygenase Homo sapiens benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00014
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00015
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00015
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00016
-
5-lipoxygenase inhibited in neutrophils Homo sapiens N-(3-phenoxycinnamyl)-acetohydroxamic acid
0.00017
-
recombinant 5-lipoxygenase Homo sapiens benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00023
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00025
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0003
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
0.00032
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00033
-
recombinant 5-lipoxygenase Homo sapiens ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.00034
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00035
-
5-lipoxygenase inhibited in neutrophils Homo sapiens benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00044
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
0.00045
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00048
-
5-lipoxygenase inhibited in neutrophils Homo sapiens benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00049
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0005
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00052
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00052
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00058
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
0.0006
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00065
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.00065
-
recombinant 5-lipoxygenase Homo sapiens ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0007
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0007
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
0.0008
-
recombinant 5-lipoxygenase Homo sapiens zileuton
0.0009
-
5-lipoxygenase inhibited in neutrophils Homo sapiens zileuton
0.0012
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0012
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0012
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0012
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
0.0016
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0017
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0017
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0017
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0017
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
0.0018
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.002
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
0.002
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0021
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
0.0024
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
0.0028
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
0.0028
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0028
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
0.0033
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
0.0034
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-(benzylamino)-1H-indole-3-carboxylate
0.0034
-
recombinant 5-lipoxygenase Homo sapiens ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
0.0035
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
0.0035
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
0.0039
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
0.004
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-(benzylamino)-1H-indole-3-carboxylate
0.0043
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
0.0048
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
0.0055
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
0.0055
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
0.0057
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
0.0065
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0069
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-(diallylamino)-1H-indole-3-carboxylate
0.007
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.0072
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0073
-
recombinant 5-lipoxygenase Homo sapiens ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
0.0079
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
0.0081
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0083
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
0.0098
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0098
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
0.01
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
0.01
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
0.01
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
0.0102
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
0.0125
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-(diallylamino)-1H-indole-3-carboxylate
0.0134
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
0.03
-
5-lipoxygenase inhibited in neutrophils Homo sapiens methyl 2-(allylamino)-1H-indole-3-carboxylate
0.03
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
0.03
-
5-lipoxygenase inhibited in neutrophils Homo sapiens ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate
0.03
-
recombinant 5-lipoxygenase Homo sapiens methyl 2-(allylamino)-1H-indole-3-carboxylate
0.03
-
recombinant 5-lipoxygenase Homo sapiens ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate