BRENDA - Enzyme Database show

Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template

Woo, L.W.; Jackson, T.; Putey, A.; Cozier, G.; Leonard, P.; Acharya, K.R.; Chander, S.K.; Purohit, A.; Reed, M.J.; Potter, B.V.; J. Med. Chem. 53, 2155-2170 (2010)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
3.1.6.2
(12aS)-N,N-dihydroxy-12a-methyl-1,3-dioxo-2-propyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinoline-8-sulfinamide
-
Homo sapiens
3.1.6.2
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
-
Homo sapiens
3.1.6.2
2-bromo-4-[(R)-(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]-N,N-dihydroxybenzenesulfinamide
-
Homo sapiens
3.1.6.2
2-[3-[[(4-[[(aminooxy)sulfinyl]oxy]phenyl)sulfanyl]methyl]-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
68.2% inhibition at 0.01 mM
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-chloro-5-(1H-1,2,4-triazol-1-ylmethyl)biphenyl-2-carbonitrile
-
Homo sapiens
3.1.6.2
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
5-((1H-1,2,4-triazol-1-yl)methyl)-3'-chloro-4'-hydroxybiphenyl-2-carbonitrile
-
Homo sapiens
3.1.6.2
5-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile
-
Homo sapiens
3.1.6.2
anastrozole
-
Homo sapiens
3.1.6.2
additional information
not inhibited by letrozole, 5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl dimethylsulfamate, 5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl dimethylsulfamate, 5'-((1H-1,2,4-triazol-1-yl)methyl)-4-chloro-2'-cyanobiphenyl-3-yl sulfamate, 3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-3-yl sulfamate, 3'-((1H-1,2,4-triazol-1-yl)methyl)-5'-cyanobiphenyl-4-yl sulfamate, 2'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate, and 3'-((1H-1,2,4-triazol-1-yl)methyl)-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
Homo sapiens
3.1.6.2
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
Homo sapiens
3.1.6.2
N,N-dimethoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
Homo sapiens
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
3.1.6.2
Homo sapiens
-
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
3.1.6.2
JEG-3 cell
-
Homo sapiens
-
3.1.6.2
liver
-
Homo sapiens
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
3.1.6.2
estrone sulfate + H2O
-
705062
Homo sapiens
estrone + sulfate
-
-
-
?
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
3.1.6.2
0.0000015
-
-
Homo sapiens
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
3.1.6.2
0.0000055
-
-
Homo sapiens
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.0000163
-
-
Homo sapiens
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
3.1.6.2
0.0000286
-
-
Homo sapiens
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.0000326
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.000035
-
-
Homo sapiens
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.00005
-
-
Homo sapiens
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.00014
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.00016
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
3.1.6.2
0.0055
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
3.1.6.2
0.006333
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
3.1.6.2
0.0000015
-
-
Homo sapiens
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
3.1.6.2
0.0000055
-
-
Homo sapiens
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.0000163
-
-
Homo sapiens
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
3.1.6.2
0.0000286
-
-
Homo sapiens
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.0000326
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.000035
-
-
Homo sapiens
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.00005
-
-
Homo sapiens
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.00014
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
3.1.6.2
0.00016
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
3.1.6.2
0.0055
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
3.1.6.2
0.006333
-
-
Homo sapiens
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
3.1.6.2
(12aS)-N,N-dihydroxy-12a-methyl-1,3-dioxo-2-propyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinoline-8-sulfinamide
-
Homo sapiens
3.1.6.2
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
-
Homo sapiens
3.1.6.2
2-bromo-4-[(R)-(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]-N,N-dihydroxybenzenesulfinamide
-
Homo sapiens
3.1.6.2
2-[3-[[(4-[[(aminooxy)sulfinyl]oxy]phenyl)sulfanyl]methyl]-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
68.2% inhibition at 0.01 mM
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
3'-chloro-5-(1H-1,2,4-triazol-1-ylmethyl)biphenyl-2-carbonitrile
-
Homo sapiens
3.1.6.2
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
Homo sapiens
3.1.6.2
5-((1H-1,2,4-triazol-1-yl)methyl)-3'-chloro-4'-hydroxybiphenyl-2-carbonitrile
-
Homo sapiens
3.1.6.2
5-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile
-
Homo sapiens
3.1.6.2
anastrozole
-
Homo sapiens
3.1.6.2
additional information
not inhibited by letrozole, 5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl dimethylsulfamate, 5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl dimethylsulfamate, 5'-((1H-1,2,4-triazol-1-yl)methyl)-4-chloro-2'-cyanobiphenyl-3-yl sulfamate, 3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-3-yl sulfamate, 3'-((1H-1,2,4-triazol-1-yl)methyl)-5'-cyanobiphenyl-4-yl sulfamate, 2'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate, and 3'-((1H-1,2,4-triazol-1-yl)methyl)-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
Homo sapiens
3.1.6.2
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
Homo sapiens
3.1.6.2
N,N-dimethoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
Homo sapiens
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
3.1.6.2
JEG-3 cell
-
Homo sapiens
-
3.1.6.2
liver
-
Homo sapiens
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
3.1.6.2
estrone sulfate + H2O
-
705062
Homo sapiens
estrone + sulfate
-
-
-
?