NADPH → HCID 70655083, compound
Reaction equation
[CH3:1][C:2]([NH:6][CH2:7][C@@H:8]1[CH2:13][N:12]([S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH2:11][CH2:10][N:9]1[C:22]1[CH:27]=[CH:26][C:25]([C@@:28]([OH:34])([CH3:33])[C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=1)([CH3:5])[CH2:3][OH:4].CC(NC[C@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC([C@](O)(C)C(F)(F)F)=CC=1)(C)CO.CC(NC[C@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC([C@@](O)(C)C(F)(F)F)=CC=1)(C)CO.C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O)C=2N=1>>[CH3:5][C:2]([NH:6][CH2:7][C@@H:8]1[CH2:13][N:12]([S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:16])[CH2:11][CH2:10][N:9]1[C:22]1[CH:27]=[CH:26][C:25]([C@:28]([OH:34])([CH3:33])[C:29]([F:30])([F:31])[F:32])=[CH:24][CH:23]=1)([CH3:1])[CH2:3][OH:4]Participants
Procedure
2-methyl-2-((((2R)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)amino)-1-propanol; 2-methyl-2-((((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)amino)-1-propanol; 2-methyl-2-((((2S)-4-(2-thiophenylsulfonyl)-1-(4-((1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)amino)-1-propanol. 1H NMR (400 MHz, CDCl3) δ 7.65-7.64 (m, 1H), 7.58-7.56 (m, 1H), 7.44-7.42 (d, J=8.6 Hz, 2H), 7.18-7.15 (m, 1H), 6.86-6.83 (d, J=8.6 Hz, 2H), 3.93-3.86 (m, 2H), 3.78-3.73 (m, 1H), 3.51-3.46 (m, 1H), 3.34-3.21 (m, 3H), 2.92-2.87 (m, 1H), 2.72-2.59 (m, 3H), 1.74 (s, 3H), 1.03 (s, 3H), 1.02 (s, 3H). m/z (ESI, +ve ion) 522.2 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=2.97 μM; GK-GKRP EC50 (LC MS/MS)=2.78 μM
Sources & evidence
- ORD record
- ord-b4265d5e10d649d2ad8ef559ba9b058d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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