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Literature summary for 1.14.14.19 extracted from

  • Hu, Q.; Negri, M.; Jahn-Hoffmann, K.; Zhuang, Y.; Olgen, S.; Bartels, M.; Mueller-Vieira, U.; Lauterbach, T.; Hartmann, R.W.
    Synthesis, biological evaluation, and molecular modeling studies of methylene imidazole substituted biaryls as inhibitors of human 17alpha-hydroxylase-17,20-lyase (CYP17)--part II: Core rigidification and influence of substituents at the methylene bridge (2008), Bioorg. Med. Chem., 16, 7715-7727.
    View publication on PubMed

Application

Application Comment Organism
medicine CYP17 inhibitors are synthesized for the potential treatment of prostate cancer Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli cells Homo sapiens
gene CYp17, expression in Escherichia coli, coexpression with human cytochrome P450 reductase Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
Homo sapiens
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
Homo sapiens
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
Homo sapiens
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
Homo sapiens
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
Homo sapiens
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
Homo sapiens
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
Homo sapiens
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
Homo sapiens
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
Homo sapiens
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
Homo sapiens
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
Homo sapiens
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
Homo sapiens
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
Homo sapiens
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
Homo sapiens
1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
-
Homo sapiens
1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
-
Homo sapiens
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
Homo sapiens
1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
-
Homo sapiens
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
Homo sapiens
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
Homo sapiens
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
Homo sapiens
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
Homo sapiens
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
Homo sapiens
4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
-
Homo sapiens
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
Homo sapiens
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
Homo sapiens
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
Homo sapiens
abiraterone
-
Homo sapiens
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
Homo sapiens
ketoconazole
-
Homo sapiens
additional information molecular modelling and docking studies, overview Homo sapiens
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
Homo sapiens
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
Homo sapiens
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
-
Homo sapiens
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
pregnenolone + AH2 + O2 Homo sapiens
-
17alpha-hydroxypregnenolone + A + H2O
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2 Homo sapiens
-
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Homo sapiens
-
gene CYP17
-

Source Tissue

Source Tissue Comment Organism Textmining
prostate cancer cell
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
pregnenolone + AH2 + O2
-
Homo sapiens 17alpha-hydroxypregnenolone + A + H2O
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
-
Homo sapiens 17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Synonyms

Synonyms Comment Organism
17alpha-hydroxylase-17,20-lyase
-
Homo sapiens
CYP17
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000072
-
abiraterone
-
Homo sapiens
0.000099
-
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
Homo sapiens
0.000112
-
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
Homo sapiens
0.000118
-
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
Homo sapiens
0.000168
-
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
Homo sapiens
0.000282
-
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
Homo sapiens
0.0003
-
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
Homo sapiens
0.00031
-
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
Homo sapiens
0.000345
-
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
Homo sapiens
0.000375
-
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
Homo sapiens
0.000388
-
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
Homo sapiens
0.00045
-
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
Homo sapiens
0.00046
-
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
Homo sapiens
0.00058
-
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
Homo sapiens
0.000756
-
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
Homo sapiens
0.00078
-
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
Homo sapiens
0.00079
-
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
Homo sapiens
0.00105
-
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
Homo sapiens
0.0013
-
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
Homo sapiens
0.0014
-
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
Homo sapiens
0.0017
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
Homo sapiens
0.002
-
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole more than 0.002000 Homo sapiens
0.0021
-
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
Homo sapiens
0.0022
-
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
Homo sapiens
0.0023
-
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
Homo sapiens
0.00278
-
ketoconazole
-
Homo sapiens
0.0031
-
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole more than 0.003100 Homo sapiens
0.0038
-
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
Homo sapiens
0.005
-
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole more than 0.005000 Homo sapiens
0.005
-
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole more than 0.005000 Homo sapiens
0.005
-
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile more than 0.005000 Homo sapiens
0.005
-
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole more than 0.005000 Homo sapiens
0.005
-
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine more than 0.005000 Homo sapiens
0.005
-
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide more than 0.005000 Homo sapiens
0.005
-
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol more than 0.005000 Homo sapiens
0.005
-
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole more than 0.005000 Homo sapiens
0.005
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine more than 0.005000 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000072
-
-
Homo sapiens abiraterone
0.000099
-
-
Homo sapiens 7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
0.000112
-
-
Homo sapiens 1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
0.000118
-
-
Homo sapiens 2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
0.000168
-
-
Homo sapiens 1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
0.000282
-
-
Homo sapiens 2-(1-imidazol-1-yl-ethyl)-9H-carbazole
0.0003
-
-
Homo sapiens 1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
0.00031
-
-
Homo sapiens 1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
0.000345
-
-
Homo sapiens 1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
0.000375
-
-
Homo sapiens 4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
0.000388
-
-
Homo sapiens 1-((9H-fluoren-2-yl)methyl)-1H-imidazole
0.00045
-
-
Homo sapiens 1-(1-biphenyl-4-yl-propyl)-1H-imidazole
0.00046
-
-
Homo sapiens 1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
0.00058
-
-
Homo sapiens 1-(1-biphenyl-4-yl-butyl)-1H-imidazole
0.000756
-
-
Homo sapiens 1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
0.00078
-
-
Homo sapiens 1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
0.00079
-
-
Homo sapiens 1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
0.00105
-
-
Homo sapiens 1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
0.0013
-
-
Homo sapiens 1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
0.0014
-
-
Homo sapiens 1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
0.0017
-
-
Homo sapiens [4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
0.002
-
-
Homo sapiens 1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
0.0021
-
-
Homo sapiens 1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
0.0022
-
-
Homo sapiens 4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
0.0023
-
-
Homo sapiens 1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
0.00278
-
-
Homo sapiens ketoconazole
0.0031
-
-
Homo sapiens 1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
0.0038
-
-
Homo sapiens 1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
0.005
-
-
Homo sapiens 1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
0.005
-
-
Homo sapiens 1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
0.005
-
-
Homo sapiens 4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
0.005
-
-
Homo sapiens 1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
0.005
-
-
Homo sapiens diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
0.005
-
-
Homo sapiens N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
0.005
-
-
Homo sapiens 3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
0.005
-
-
Homo sapiens 1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
0.005
-
-
Homo sapiens [4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine