NADPH → HCID 178513078, compound

HRID 1766173Notes

Reaction equation

HRID 1766173 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([C:20]([NH:22][C:23]([NH2:25])=[NH:24])=[O:21])=[CH:12]2)=[CH:3][CH:2]=1.[Mg+2].[Cl-].[Cl-].C1N=C(N)C2N=CN([C@@H]3[O:42][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.C1C(=O)NC(=O)N([C@@H]2O[C@H](COP(OP(O[C@H]3O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=1>C(#N)C>[OH:42][C:2]1[CH:3]=[C:4]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([C:20]([NH:22][C:23]([NH2:25])=[NH:24])=[O:21])=[CH:12]2)[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

6

Reactant 4

HCID 5884NADPH2×HCID 17473Udp-glucuronic acidHCID 5360315Magnesium ChlorideHCID 178513073HCID 178513073, compound

Product 1

HCID 178513078HCID 178513078, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.8 mg of N-(1-quinolin-4-yl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-guanidine were dissolved using 150 ml of an aqueous solution containing 381 mg MgCl2, 1.3 mM NADPH (Dihydronicotinamide adenine dinucleotide phosphate, Calbiochem product number: 481973; Shen, A. L., et al. 1989. J. Biol. Chem. 264, 7584; Yamano, S., et al. 1989. Mol. Pharmacol. 36, 83.), 300 mg of human S9 fraction and 2.5 mM UDPGA (Uridine 5′-diphosphoglucuronic acid trisodium salt, Sigma catalog number U6751). The mixture was incubated for 120 minutes at 37° C. Then, 40 ml of acetonitrile were added, proteins centrifuged and decanted. This solution was concentrated to 100 ml and chromatographed using the system described below. The solvents were removed under reduced pressure to yield 0.9 mg of N-[1-(2-hydroxy-quinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-guanidine as an amorphous solid.

Workup

  1. customdecanted
  2. concentrationThis solution was concentrated to 100 ml
  3. customchromatographed
  4. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-b68fa4f6388441388165def11d5c1e30
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

Loading…