Dimethyl Sulfoxide → Artesunate

HRID 2175672Notes

Reaction equation

HRID 2175672 reaction equation
CS(C)=O.[CH3:5][C@H:6]1[C@@H:15]2[CH2:16][CH2:17][C@@:18]3([CH3:22])[O:20][O:21][C@:14]42[C@H:9]([C@@H:10]([CH3:31])[C@H:11]([O:23][C:24]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:25])[O:12][C@@H:13]4[O:19]3)[CH2:8][CH2:7]1.C(=O)(O)[O-].[Na+:36]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].Cl[Ru]Cl.Cl[Ru]Cl>[CH3:5][C@H:6]1[C@@H:15]2[CH2:16][CH2:17][C@@:18]3([CH3:22])[O:20][O:21][C@:14]42[C@H:9]([C@@H:10]([CH3:31])[C@H:11]([O:23][C:24]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:25])[O:12][C@@H:13]4[O:19]3)[CH2:8][CH2:7]1.[CH3:5][C@H:6]1[C@@H:15]2[CH2:16][CH2:17][C@@:18]3([CH3:22])[O:20][O:21][C@:14]42[C@H:9]([C@@H:10]([CH3:31])[C@@H:11]([O:23][C:24]([CH2:26][CH2:27][C:28]([O-:30])=[O:29])=[O:25])[O:12][C@@H:13]4[O:19]3)[CH2:8][CH2:7]1.[Na+:36]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 6917864Artesunate

Product 2

HCID 6917864ArtesunateHCID 23697153HCID 23697153, compound

Reagents, catalysts & solvents 1

HCID 10951331Carbon monooxide--dichlororuthenium (3/1)Catalyst2×

Procedure

CORM-2 (Sigma-Aldrich) and Compound 2 were solubilized using 10% dimethyl sulfoxide (DMSO; Sigma-Aldrich) in PBS. CORM-3 and Compound 1 were solubilized in PBS (1×). CORM-2 solution (20 mg/kg of body weight) was administered intravenously (i.v.) according to the chosen schedules. Compound 2, CORM-3 and Compound 1 were administered i.v. at equimolar concentrations relative to CORM-2 (36.7 mg/Kg). As vehicle control, we used a solution of 10% DMSO in PBS administered i.v. The concentrations of CORM-2 used in the present study were based on previous reports (see, e.g., Chen et al. Am. J. Pathol. (2009) 175:422-429; Sun et al., World. J. Gastroenterol. (2008) 14:547-553). Artesunate is presented as a powder of artesunic acid. Artesunate (AS) solution was prepared by dissolving 60 mg of anhydrous artesunic acid in 1 ml of sodium bicarbonate (5%) to form sodium artesunate and then diluted in 5 ml of NaCl (0.9%). An AS solution (i.p.) was administered at 40 mg/Kg/day, as described previously (see, e.g., Bienvenu, Acta Trop (2008) 106:104-108). The AS treatment was started when the infected non-treated mice presented the clinical stage 1 for experimental cerebral malaria.

Workup

  1. concentrationat equimolar concentrations relative to CORM-2 (36.7 mg/Kg)

Sources & evidence

ORD record
ord-40e8dc03b0da4e088a57305f09857ed8
Source dataset
uspto-grants-2015_06
Patent number
US09062089B2

Reaction notes

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