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Literature summary for 1.14.14.18 extracted from

  • Roman, G.; Riley, J.G.; Vlahakis, J.Z.; Kinobe, R.T.; Brien, J.F.; Nakatsu, K.; Szarek, W.A.
    Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring (2007), Bioorg. Med. Chem., 15, 3225-3234.
    View publication on PubMed
Search for more literature for 1.14.14.18

Inhibitors

Inhibitors Comment Organism Structure
(+-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride IC50: 0.00006 mM Rattus norvegicus
(+-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride IC50: 0.0062 mM Rattus norvegicus
(+-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride IC50: 0.00014 mM Rattus norvegicus
(+-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride IC50: 0.0005 mM Rattus norvegicus
(+-)-4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride IC50: 0.0014 mM Rattus norvegicus
(+/-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride
-
 Rattus norvegicus
(+/-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride
-
 Rattus norvegicus
(+/-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
-
 Rattus norvegicus
(+/-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
-
 Rattus norvegicus
1-((2-(2-(4-bromophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride IC50: 0.0019 mM Rattus norvegicus
1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride IC50: 0.0043 mM Rattus norvegicus
1-((2-(2-(4-fluorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride IC50: 0.0038 mM Rattus norvegicus
1-((2-(2-(4-iodophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride IC50: 0.0037 mM Rattus norvegicus
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride IC50: 0.0007 mM Rattus norvegicus
1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanone hydrochloride IC50: 0.00011 mM Rattus norvegicus
1-(1H-imidazol-1-yl)-4-phenyl-2-butanone hydrochloride IC50: 0.004 mM Rattus norvegicus
2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes
-
 Rattus norvegicus
4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride IC50: 0.0017 mM Rattus norvegicus
4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride IC50: 0.0047 mM Rattus norvegicus
4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride IC50: 0.0027 mM Rattus norvegicus
azalanstat IC50: 0.0053 mM Rattus norvegicus
additional information synthesis of a series of 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes comprising imidazole-ketones, imidazole-dioxolanes, and imidazole-alcohols substituted with halogens in the phenyl ring, evaluation of the inhibitory potency on heme oxygenase, overview Rattus norvegicus

Localization

Localization Comment Organism GeneOntology No. Textmining
microsome
-
 Rattus norvegicus
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
heme + AH2 + O2 Rattus norvegicus
-
 biliverdin + Fe2+ + CO + A + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-
Rattus norvegicus
-
 constitutive isozyme HO-2
-
Rattus norvegicus
-
 inducible isozyme HO-1
-

Source Tissue

Source Tissue Comment Organism Textmining
brain isozyme HO-2 Rattus norvegicus
-
spleen
-
 Rattus norvegicus
-
spleen isozyme HO-1 Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
heme + AH2 + O2
-
 Rattus norvegicus biliverdin + Fe2+ + CO + A + H2O
-
 ?
heme + electron donor + O2
-
 Rattus norvegicus biliverdin + Fe2+ + CO + oxidized eletron donor + H2O
-
 ?

Synonyms

Synonyms Comment Organism
heme oxygenase-1
-
 Rattus norvegicus
heme oxygenase-2
-
 Rattus norvegicus
HO-1
-
 Rattus norvegicus
HO-2
-
 Rattus norvegicus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Rattus norvegicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00006
-
 IC50: 0.00006 mM Rattus norvegicus (+-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride
0.00011
-
 IC50: 0.00011 mM Rattus norvegicus 1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanone hydrochloride
0.00014
-
 IC50: 0.00014 mM Rattus norvegicus (+-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
0.0005
-
 IC50: 0.0005 mM Rattus norvegicus (+-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
0.0007
-
 IC50: 0.0007 mM Rattus norvegicus 1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
0.0014
-
 IC50: 0.0014 mM Rattus norvegicus (+-)-4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
0.0017
-
 IC50: 0.0017 mM Rattus norvegicus 4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
0.0019
-
 IC50: 0.0019 mM Rattus norvegicus 1-((2-(2-(4-bromophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
0.0027
-
 IC50: 0.0027 mM Rattus norvegicus 4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
0.0037
-
 IC50: 0.0037 mM Rattus norvegicus 1-((2-(2-(4-iodophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
0.0038
-
 IC50: 0.0038 mM Rattus norvegicus 1-((2-(2-(4-fluorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
0.004
-
 IC50: 0.004 mM Rattus norvegicus 1-(1H-imidazol-1-yl)-4-phenyl-2-butanone hydrochloride
0.0043
-
 IC50: 0.0043 mM Rattus norvegicus 1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
0.0047
-
 IC50: 0.0047 mM Rattus norvegicus 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
0.0053
-
 IC50: 0.0053 mM Rattus norvegicus azalanstat
0.0062
-
 IC50: 0.0062 mM Rattus norvegicus (+-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride
0.06
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus (+/-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride
0.11
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanone hydrochloride
0.14
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus (+/-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
0.5
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus (+/-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
0.7
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
1.4
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
1.7
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
1.8
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanone hydrochloride
1.8
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus (+/-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride
1.9
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
1.9
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-((2-(2-(4-bromophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
2.6
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus (+/-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
2.7
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
3.7
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-((2-(2-(4-iodophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
3.8
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-((2-(2-(4-fluorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
4
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus (+/-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
4
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-(1H-imidazol-1-yl)-4-phenyl-2-butanone hydrochloride
4.3
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
4.7
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
5.3
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus azalanstat
6.2
-
 pH 7.4, 37°C, spleen isozyme HO-1 Rattus norvegicus (+/-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride
9.5
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
11.3
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-(1H-imidazol-1-yl)-4-phenyl-2-butanone hydrochloride
16
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus (+/-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride
17.9
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
24.5
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus azalanstat
43.1
-
 pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone hydrochloride
100
-
 above, pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
100
-
 above, pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
100
-
 above, pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-((2-(2-(4-fluorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
100
-
 above, pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-((2-(2-(4-bromophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
100
-
 above, pH 7.4, 37°C, brain isozyme HO-2 Rattus norvegicus 1-((2-(2-(4-iodophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride