NADPH → HCID 70655253, compound
Reaction equation
[F:1][C:2]([F:36])([F:35])[C@@:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@H:13]2[CH2:26][O:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@@H]2COCC2C=NC=CC=2)=CC=1)(O)C.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@H]2COCC2C=NC=CC=2)=CC=1)(O)C.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>>[F:36][C:2]([F:1])([F:35])[C@@:3]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:26][O:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:10][CH:11]=1)([OH:5])[CH3:4]Participants
Procedure
(2R)-1,1,1-trifluoro-2-(4-((2S)-2-((3-pyridinylmethoxy)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2R)-2-((3-pyridinylmethoxy)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol; (2S)-1,1,1-trifluoro-2-(4-((2S)-2-((3-pyridinylmethoxy)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol. 1H NMR (400 MHz, CDCl3) δ 8.40-8.38 (m, 1H), 7.67-7.65 (m, 1H), 7.60-7.58 (m, 1H), 7.52-7.46 (m, 3H), 7.45-7.39 (m, 1H), 7.22-7.18 (m, 2H), 6.88-6.86 (m, 2H), 4.45-4.35 (m, 2H), 4.26-4.22 (m, 1H), 3.91-3.77 (m, 3H), 3.73-3.69 (m, 1H), 3.41-3.27 (m, 2H), 2.84-2.79 (m, 1H), 2.69-2.60 (m, 1H), 1.74 (s, 3H). m/z (ESI, +ve ion) 542.1 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=4.93 μM; GK-GKRP EC50 (LC MS/MS)=4.93 μM.
Sources & evidence
- ORD record
- ord-9613661b10154f58930295bba9cd63cb
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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