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Literature summary extracted from

  • Heinrich, D.M.; Flanagan, J.U.; Jamieson, S.M.; Silva, S.; Rigoreau, L.J.; Trivier, E.; Raynham, T.; Turnbull, A.P.; Denny, W.A.
    Synthesis and structure-activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3 (2013), Eur. J. Med. Chem., 62, 738-744.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.1.1.64 in complex with inhibitor 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one. The 2-pyrrolidinone does not interact directly with residues in the oxyanion hole Homo sapiens
1.1.1.213 in complex with inhibitor 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one. The 2-pyrrolidinone does not interact directly with residues in the oxyanion hole Homo sapiens
1.1.1.239 in complex with inhibitor 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one. The 2-pyrrolidinone does not interact directly with residues in the oxyanion hole Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.64 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 11 nM Homo sapiens
1.1.1.64 1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 22 nM Homo sapiens
1.1.1.64 1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM Homo sapiens
1.1.1.213 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 11 nM Homo sapiens
1.1.1.213 1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 22 nM Homo sapiens
1.1.1.213 1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM Homo sapiens
1.1.1.239 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 11 nM Homo sapiens
1.1.1.239 1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 22 nM Homo sapiens
1.1.1.239 1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.64 Homo sapiens P42330
-
-
1.1.1.213 Homo sapiens P42330
-
-
1.1.1.239 Homo sapiens P42330
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining

Synonyms

EC Number Synonyms Comment Organism
1.1.1.64 AKR1C3
-
 Homo sapiens
1.1.1.213 AKR1C3
-
 Homo sapiens
1.1.1.239 AKR1C3
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.64 0.000052
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
1.1.1.64 0.000056
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
1.1.1.64 0.000094
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
1.1.1.213 0.000052
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
1.1.1.213 0.000056
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
1.1.1.213 0.000094
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
1.1.1.239 0.000052
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
1.1.1.239 0.000056
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
1.1.1.239 0.000094
-
 pH not specified in the publication, temperature not specified in the publication Homo sapiens 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one