NADPH → HCID 66582536, compound

HRID 1972365Notes

Reaction equation

[CH3:1][C:2]([OH:34])([C:4]#[C:5][C:6]1[CH:7]=[C:8]([C:21]2[CH:26]=[CH:25][C:24]([C@:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)[CH:9]=[CH:10][C:11]=1[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH3:3].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>>[CH3:3][C:2]([OH:34])([C:4]#[C:5][C:6]1[CH:7]=[C:8]([C:21]2[CH:22]=[CH:23][C:24]([C@@:27]([OH:33])([CH3:32])[C:28]([F:31])([F:29])[F:30])=[CH:25][CH:26]=2)[CH:9]=[CH:10][C:11]=1[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH3:1]

Participants

Reactant 2

HCID 5884NADPH

HCID 66582496HCID 66582496, compound

Product 1

HCID 66582536HCID 66582536, compound

Procedure

2-methyl-4-(4-(phenylsulfonyl)-4′-((1R)-2,2,2-trifluoro-1-hydroxy-1-methylethyl)-3-biphenylyl)-3-butyn-2-ol. 1H NMR (400 MHz, CD3OD) δ 8.34 (d, J=8.2 Hz, 1H), 8.05 (d, J=7.8 Hz, 2H), 7.92-7.81 (m, 2H), 7.79-7.66 (m, 5H), 7.64-7.55 (m, 2H), 1.77 (s, 3H), 1.59 (s, 6H). m/z (ESI, +ve ion) 471.0 (M-OH)+. GK-GKRP EC50 (NADPH-coupled)=1.80 μM; GK-GKRP EC50 (LC MS/MS)=2.25 μM.

Sources & evidence

ORD record: ord-4676cfe4e9e44621a127364176d81827
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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