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Literature summary for 1.14.14.19 extracted from

  • Owen, C.P.; Shahid, I.; Lee, W.Y.; Ahmed, S.
    Synthesis and biochemical evaluation of a range of (4-substituted phenyl)sulfonate derivatives of 4-hydroxybenzyl imidazole-based compounds as potent inhibitors of 17alpha-hydroxylase/17,20-lyase (P45017alpha) derived from rat testicular microsomes (2010), Bioorg. Med. Chem. Lett., 20, 5345-5348.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1-(4-iodobenzyl)-1H-imidazole
-
Rattus norvegicus
1-benzyl-1H-imidazole
-
Rattus norvegicus
1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenol
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
-
Rattus norvegicus
4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
-
Rattus norvegicus
4-hydroxybenzyl imidazole
-
Rattus norvegicus
4-iodobenzyl imidazole
-
Rattus norvegicus
abiraterone acetate
-
Rattus norvegicus
benzyl imidazole
-
Rattus norvegicus
ketoconazole
-
Rattus norvegicus
additional information synthesis and inhibitory activity of a range of 4-substituted phenylsulfonate derivatives of 4-hydroxybenzyl imidazole against the two components of 17alpha-hydroxylase/17,20-lyase, namely, 17alpha-hydroxylase and 17,20-lyase, overview Rattus norvegicus
toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
-
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.
progesterone + AH2 + O2 Rattus norvegicus
-
17alpha-hydroxyprogesterone + A + H2O
-
?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
testis
-
Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information both hydroxylation and C-C-bond cleavage steps require NADPH and oxygen Rattus norvegicus ?
-
?
progesterone + AH2 + O2
-
Rattus norvegicus 17alpha-hydroxyprogesterone + A + H2O
-
?

Synonyms

Synonyms Comment Organism
17alpha-hydroxylase/17,20-lyase
-
Rattus norvegicus
P45017alpha
-
Rattus norvegicus

Cofactor

Cofactor Comment Organism Structure
NADPH required Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00001
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
0.00001
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
0.000014
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
0.000014
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
0.00002
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
0.00002
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
0.00003
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
0.00003
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
0.00003
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
0.00003
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
0.000034
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
0.000034
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
0.00004
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
0.00004
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
0.00004
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
0.00004
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
0.00007
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
0.00007
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
0.0001
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
0.0001
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
0.00011
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
0.00011
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
0.00013
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
0.00013
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
0.00016
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
0.00016
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
0.000164
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-iodobenzyl imidazole
0.000164
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 1-(4-iodobenzyl)-1H-imidazole
0.0002
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
0.0002
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
0.000206
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus ketoconazole
0.000206
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
0.00073
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-iodobenzyl imidazole
0.00104
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
0.00104
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
0.00121
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
0.00121
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
0.00147
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus 4-hydroxybenzyl imidazole
0.00147
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenol
0.002496
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus 4-hydroxybenzyl imidazole
0.0025
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenol
0.00266
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus ketoconazole
0.00266
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
0.003
-
IC50 above 0.003 mM against 17,20-lyase activity, pH and temperature not specified in the publication Rattus norvegicus benzyl imidazole
0.003
-
IC50 above 0.003 mM against 17alpha-hydroxylase activity, pH and temperature not specified in the publication Rattus norvegicus benzyl imidazole
0.003
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 1-benzyl-1H-imidazole
0.003
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 1-benzyl-1H-imidazole
0.0076
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication Rattus norvegicus 1-(4-iodobenzyl)-1H-imidazole