NADPH → HCID 86670335, compound
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:41])([F:40])[C@@:10]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)(=[O:27])=[O:26])[CH2:21][C@@H:20]2[CH2:33][C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[CH:15][CH:14]=1)([OH:12])[CH3:11].FC(F)(F)C(O)=O.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@H]2CC2C=CN=CC=2)=CC=1)(O)C.FC(F)(F)C(O)=O.FC(F)(F)[C@](C1C=CC(N2CCN(S(C3SC=CC=3)(=O)=O)C[C@@H]2CC2C=CN=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:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:41][C:9]([F:8])([F:40])[C@@:10]([C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)(=[O:27])=[O:26])[CH2:21][C@H:20]2[CH2:33][C:34]2[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=2)=[CH:17][CH:18]=1)([OH:12])[CH3:11]Participants
Procedure
(2R)-1,1,1-trifluoro-2-(4-((2S)-2-(4-pyridinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol trifluoroacetate; (2S)-1,1,1-trifluoro-2-(4-((2R)-2-(4-pyridinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol trifluoroacetate; (2S)-1,1,1-trifluoro-2-(4-((2S)-2-(4-pyridinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol trifluoroacetate. 1H NMR (300 MHz, CD3OD) δ 8.61 (d, J=6.4 Hz, 2H), 7.80-7.93 (m, 3H), 7.62 (dd, J=3.8, 1.2 Hz, 1H), 7.43 (d, J=8.6 Hz, 2H), 7.20-7.29 (m, 1H), 6.95 (d, J=8.9 Hz, 2H), 4.48 (s, 1H), 3.86 (s, 1H), 3.45-3.63 (m, 3H), 3.34-3.45 (m, 1H), 3.16 (dd, J=13.0, 5.7 Hz, 1H), 2.53-2.71 (m, 2H), 1.67 (s, 3H). m/z (ESI, +ve ion) 512.2 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.207 μM; GK-GKRP EC50 (LC MS/MS)=0.522 μM.
Sources & evidence
- ORD record
- ord-5f9586351c8a44bd952aca3a75107998
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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