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Literature summary for 1.14.15.4 extracted from

  • Roumen, L.; Peeters, J.W.; Emmen, J.M.; Beugels, I.P.; Custers, E.M.; de Gooyer, M.; Plate, R.; Pieterse, K.; Hilbers, P.A.; Smits, J.F.; Vekemans, J.A.; Leysen, D.; Ottenheijm, H.C.; Janssen, H.M.; Hermans, J.J.
    Synthesis, biological evaluation, and molecular modeling of 1-benzyl-1H-imidazoles as selective inhibitors of aldosterone synthase (CYP11B2) (2010), J. Med. Chem., 53, 1712-1725.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1-(3-bromobenzyl)-1H-imidazole
-
Homo sapiens
1-(3-chlorobenzyl)-1H-imidazole
-
Homo sapiens
1-(3-cyanobenzyl)-1H-imidazole
-
Homo sapiens
1-(3-fluorobenzyl)-1H-imidazole
-
Homo sapiens
1-(4-aminobenzyl)-1H-imidazole
-
Homo sapiens
1-(4-bromobenzyl)-1H-imidazole
-
Homo sapiens
1-(4-bromobenzyl)-5-phenyl-1H-imidazole
-
Homo sapiens
1-(4-chlorobenzyl)-1H-imidazole
-
Homo sapiens
1-(4-chlorobenzyl)-5-phenyl-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(2-fluorophenyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(2-methylphenyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(3-fluorophenyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(3-methylphenyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(4-fluorophenyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(4-methylphenyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(4-pyridyl)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(methyl carboxylate)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-(methylene-acetate)-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-bromo-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-formyl-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-hydroxymethyl-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-methyl-1H-imidazole
-
Homo sapiens
1-(4-cyanobenzyl)-5-phenyl-1H-imidazole
-
Homo sapiens
1-(4-fluorobenzyl)-1H-imidazole
-
Homo sapiens
1-(4-fluorobenzyl)-5-phenyl-1H-imidazole
-
Homo sapiens
1-(4-methoxybenzyl)-5-phenyl-1H-imidazole
-
Homo sapiens
1-benzyl-5-phenyl-1H-imidazole
-
Homo sapiens
3-(1-benzyl-1H-imidazol-5-yl)-1-propanol
-
Homo sapiens
3-(1H-imidazol-1-ylmethyl)aniline
-
Homo sapiens
3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-1-propanol
-
Homo sapiens
3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-1-propanol
-
Homo sapiens
3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-1-propanol
-
Homo sapiens
3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-1-propanol
-
Homo sapiens
3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-1-propanol
-
Homo sapiens
4-((5-phenyl-1H-imidazol-1-yl)methyl)benzonitrile
-
Homo sapiens
methyl 3-(1-benzyl-1H-imidazol-5-yl)-propanoate
-
Homo sapiens
methyl 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-propanoate
-
Homo sapiens
methyl 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-propanoate
-
Homo sapiens
methyl 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-propanoate
-
Homo sapiens
methyl 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-propanoate
-
Homo sapiens
methyl 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-propanoate
-
Homo sapiens
additional information three-dimensional modeling of CYP11B2 to model the binding modes of the natural substrate 18-hydroxycorticosterone and the CYP11B2 inhibitor R-fadrozole, overview. Synthesis, biological evaluation, and molecular modeling of 1-benzyl-1H-imidazoles as selective inhibitors of aldosterone synthase, overview. Molecular docking in the CYP11B1 and CYP11B2 models Homo sapiens
R-fadrozole
-
Homo sapiens
S-fadrozole
-
Homo sapiens
[3-(1H-imidazol-1-ylmethyl)phenyl]methanol
-
Homo sapiens
[4-(1H-imidazol-1-ylmethyl)phenyl]methanol
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Homo sapiens CYP11B2 hydroxylates 18-hydroxycorticosterone ?
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information CYP11B2 hydroxylates 18-hydroxycorticosterone Homo sapiens ?
-
?

Synonyms

Synonyms Comment Organism
Aldosterone synthase
-
Homo sapiens
CYP11B2
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000005
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 4-((5-phenyl-1H-imidazol-1-yl)methyl)benzonitrile
0.0000017
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-phenyl-1H-imidazole
0.0000017
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 4-((5-phenyl-1H-imidazol-1-yl)methyl)benzonitrile
0.0000023
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(2-fluorophenyl)-1H-imidazole
0.0000035
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-propanoate
0.0000037
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(2-methylphenyl)-1H-imidazole
0.000004
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-propanoate
0.0000048
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-benzyl-5-phenyl-1H-imidazole
0.0000051
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-bromobenzyl)-5-phenyl-1H-imidazole
0.0000052
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(3-methylphenyl)-1H-imidazole
0.0000055
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(3-fluorophenyl)-1H-imidazole
0.0000057
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(2-methylphenyl)-1H-imidazole
0.0000058
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-chlorobenzyl)-5-phenyl-1H-imidazole
0.000006
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens R-fadrozole
0.0000062
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(3-methylphenyl)-1H-imidazole
0.0000062
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000007
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-bromobenzyl)-5-phenyl-1H-imidazole
0.000007
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(methyl carboxylate)-1H-imidazole
0.000011
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-methoxybenzyl)-5-phenyl-1H-imidazole
0.000011
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-benzyl-5-phenyl-1H-imidazole
0.000011
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-fluorobenzyl)-5-phenyl-1H-imidazole
0.000012
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-1-propanol
0.000012
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-methyl-1H-imidazole
0.000013
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000014
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-methoxybenzyl)-5-phenyl-1H-imidazole
0.000016
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-fluorobenzyl)-5-phenyl-1H-imidazole
0.000016
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000018
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-1-propanol
0.00002
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(2-fluorophenyl)-1H-imidazole
0.000023
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-bromo-1H-imidazole
0.000025
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-chlorobenzyl)-5-phenyl-1H-imidazole
0.000025
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(4-fluorophenyl)-1H-imidazole
0.000027
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(4-fluorophenyl)-1H-imidazole
0.000028
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-phenyl-1H-imidazole
0.000029
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-hydroxymethyl-1H-imidazole
0.000031
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-propanoate
0.000032
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(3-fluorophenyl)-1H-imidazole
0.00004
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens S-fadrozole
0.000044
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000044
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(methylene-acetate)-1H-imidazole
0.000048
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000048
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(methyl carboxylate)-1H-imidazole
0.00005
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-propanoate
0.000055
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000057
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-propanoate
0.000059
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-1-propanol
0.000062
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-formyl-1H-imidazole
0.000073
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-bromo-1H-imidazole
0.000104
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-propanoate
0.000111
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-propanoate
0.000116
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000117
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(4-methylphenyl)-1H-imidazole
0.000119
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens R-fadrozole
0.000121
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-propanoate
0.000123
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-propanoate
0.00013
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(4-methylphenyl)-1H-imidazole
0.000141
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-methyl-1H-imidazole
0.000143
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-bromobenzyl)-1H-imidazole
0.000151
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-chlorobenzyl)-1H-imidazole
0.000171
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens S-fadrozole
0.000177
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-propanoate
0.000181
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(1-benzyl-1H-imidazol-5-yl)-1-propanol
0.000193
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-(1-benzyl-1H-imidazol-5-yl)-propanoate
0.000206
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-fluorobenzyl)-1H-imidazole
0.000206
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens [3-(1H-imidazol-1-ylmethyl)phenyl]methanol
0.000211
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-bromobenzyl)-1H-imidazole
0.000213
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(methylene-acetate)-1H-imidazole
0.000236
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-aminobenzyl)-1H-imidazole
0.000285
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-hydroxymethyl-1H-imidazole
0.000286
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(1-benzyl-1H-imidazol-5-yl)-1-propanol
0.000307
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(4-pyridyl)-1H-imidazole
0.000326
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens methyl 3-(1-benzyl-1H-imidazol-5-yl)-propanoate
0.00033
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-fluorobenzyl)-1H-imidazole
0.000365
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-bromobenzyl)-1H-imidazole
0.000368
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-1H-imidazole
0.000372
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-1H-imidazole
0.00039
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(1H-imidazol-1-ylmethyl)aniline
0.000407
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-(4-pyridyl)-1H-imidazole
0.000457
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-chlorobenzyl)-1H-imidazole
0.000478
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-cyanobenzyl)-5-formyl-1H-imidazole
0.000479
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-bromobenzyl)-1H-imidazole
0.000494
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-fluorobenzyl)-1H-imidazole
0.0006
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 3-(1H-imidazol-1-ylmethyl)aniline
0.000695
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens [4-(1H-imidazol-1-ylmethyl)phenyl]methanol
0.000709
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-fluorobenzyl)-1H-imidazole
0.000815
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-fluorobenzyl)-1H-imidazole
0.001
-
above, inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-chlorobenzyl)-1H-imidazole
0.001
-
above, inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-cyanobenzyl)-1H-imidazole
0.001
-
above, inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-chlorobenzyl)-1H-imidazole
0.001
-
above, inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens [4-(1H-imidazol-1-ylmethyl)phenyl]methanol
0.001
-
above, inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-aminobenzyl)-1H-imidazole
0.001
-
above, inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(3-cyanobenzyl)-1H-imidazole
0.001174
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens [3-(1H-imidazol-1-ylmethyl)phenyl]methanol
0.001799
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-fluorobenzyl)-1H-imidazole