Eupatilin

Eupatilin, a lipophilic flavonoid isolated from Artemisia species, is a PPARα agonist, and possesses anti-apoptotic, anti-oxidative and anti-inflammatory activities.

Solid

Eupatilin is a trimethoxyflavone that is flavone substituted by hydroxy groups at C-5 and C-7 and methoxy groups at C-6, C-3' and C-4' respectively. Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer and antineoplastic activities. It has a role as an anti-ulcer drug, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antineoplastic agent, an anti-inflammatory agent and a metabolite. It is a trimethoxyflavone and a dihydroxyflavone.

This step is a step of performing Step-9 of FIG. 3 and will be described in detail as follows.Acetonitrile (100 mL)Was suspended (3, 4-dimethoxyphenyl) -7-hydroxy-5, 6-dimethoxy-4H-chromen-4-one (precursor compound 9)(11 g; 0.0307 mol, 1 equiv), AlCl3 (20.3 g; 0.153 mol; 5 equiv) was added in small portions at room temperature, and the mixture was refluxed at 90 DEG C for 2 hours. The reaction was complete by TLC and the solvent was evaporated to dryness. The resulting residue was treated with aqueous HCl (10percent; 200 mL) and chloroform (200 mL) and refluxed until the reaction mixture was clear. TLC (7: 3 / PE: EtOAc; After confirming completion, the reaction mixture was cooled to room temperature and the organic phase was separated. The water phase was again extracted with DCM and the organic phase was washed with water and brine solution, dried over sodium sulfate and concentrated. The residue was applied to silica gel (60-120 mesh) column chromatography and eluted with DCM to give yellow solid(3, 4-dimethoxyphenyl) -5, 7-dihydroxy-6-methoxy-4H-chromen-4-one (precursor compound 10) (yield: 7.0 g; 66percent).Compound 1-4 (100.8 mg, 0.187 mmol)And scandium triflate (Sc (OTf) 3) (46.5 mg, 0.094 mmol)Was dissolved in 1, 2-dichloroethane (1.7 mL)(70 muL) was added to the mixture at room temperature, It was refluxed in a sealed tube for 24 hours.Sodium bicarbonate solution was added to the reaction solution, and the aqueous layer was extracted with dichloromethane.The combined organic layer was washed with brine and dried over sodium sulfate.After removing the solvent under vacuum, the residue was chromatographed with ODS (35-40% acetonitrile solution)The obtained eperiniline was dried under vacuum at room temperature for 1 hour.The yield was 55.1 mg (yield: 85.6%)This step is a step of performing Step-10 of FIG. 3 and will be described in detail as follows.To a solution of the above

Molecular Weight:344.3
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:344.08960285
Monoisotopic Mass:344.08960285
Topological Polar Surface Area:94.4
Heavy Atom Count:25
Complexity:520
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes