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Literature summary for 1.14.15.4 extracted from

  • Lucas, S.; Negri, M.; Heim, R.; Zimmer, C.; Hartmann, R.W.
    Fine-tuning the selectivity of aldosterone synthase inhibitors: structure-activity and structure-selectivity insights from studies of heteroaryl substituted 1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one derivatives (2011), J. Med. Chem., 54, 2307-2319.
    View publication on PubMed

Application

Application Comment Organism
medicine treatment of hyperaldosteronism, congestive heart failure, and myocardial fibrosis by lowering the elevated plasma aldosterone levels via blockade of aldosterone synthase, CYP11B2, the key enzyme of mineralocorticoid biosynthesis Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
expression of CYP11B1 and CYP11B2 in V79 cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
6,6-dimethyl-8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(1H-imidazol-1-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(2,3'-bipyridin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(5-ethoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(5-fluoropyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(5-hydroxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(5-methoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(5-phenylpyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one
-
Homo sapiens
8-(isoquinolin-4-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-thione
-
Homo sapiens
8-(pyrimidin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(2,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(2-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(2-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(3,4-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(3,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(3-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(3-hydroxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(3-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(4-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(4-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(propan-2-yloxy)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-(trifluoromethyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
8-[5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
Homo sapiens
9-(5-methoxypyridin-3-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
-
Homo sapiens
9-(pyridin-3-yl)-1,2,6,7-tetrahydro-5H-pyrido[ 3,2,1-ij]quinolin-3-one
-
Homo sapiens
9-[6-(isoquinolin-4-yl)pyridin-3-yl]-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
-
Homo sapiens
additional information development of 1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-ones and structurally related aldosterone synthase inhibitors, molecular modelling, overview. No inhibition of both isozymes by 32 and 15 Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
mitochondrion CYP11B2 Homo sapiens 5739
-

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
adrenal gland CYP11B2 Homo sapiens
-
zona glomerulosa CYP11B2 Homo sapiens
-

Synonyms

Synonyms Comment Organism
11beta-hydroxylase
-
Homo sapiens
Aldosterone synthase
-
Homo sapiens
CYP11B1
-
Homo sapiens
CYP11B2
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000002
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(isoquinolin-4-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000002
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 9-[6-(isoquinolin-4-yl)pyridin-3-yl]-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
0.0000006
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-methoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000007
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(2-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000009
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 9-(5-methoxypyridin-3-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
0.0000009
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(4-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000001
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-ethoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000011
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000012
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3-hydroxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000012
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-thione
0.0000013
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-phenylpyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one
0.0000014
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000014
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(4-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000022
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(propan-2-yloxy)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000023
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3,4-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000024
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 9-(pyridin-3-yl)-1,2,6,7-tetrahydro-5H-pyrido[ 3,2,1-ij]quinolin-3-one
0.0000024
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(2-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000036
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(2,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000043
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-hydroxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000044
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-fluoropyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000046
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000059
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(trifluoromethyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000013
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(isoquinolin-4-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000016
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000018
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000021
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(4-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000033
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000034
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 9-[6-(isoquinolin-4-yl)pyridin-3-yl]-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
0.00004
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(4-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000043
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(2-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000044
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3-hydroxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000056
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(pyrimidin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000058
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-phenylpyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one
0.000089
-
inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(1H-imidazol-1-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000103
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(propan-2-yloxy)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000128
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(2-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000141
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(trifluoromethyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000158
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-ethoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000183
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(2,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000247
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-methoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000333
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-thione
0.00049
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000496
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3,4-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000545
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 9-(5-methoxypyridin-3-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
0.000715
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.001288
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-fluoropyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.001374
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.001748
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-(3,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.002045
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(5-hydroxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.002058
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.002077
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(1H-imidazol-1-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.002296
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 9-(pyridin-3-yl)-1,2,6,7-tetrahydro-5H-pyrido[ 3,2,1-ij]quinolin-3-one
0.004646
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-[5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.02855
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication Homo sapiens 8-(pyrimidin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

General Information

General Information Comment Organism
metabolism aldosterone synthase, CYP11B2, is the key enzyme of mineralocorticoid biosynthesis and its malfunction is involved in hyperaldosteronism, congestive heart failure, and myocardial fibrosis Homo sapiens