5-Hydroxy-7,4′-dimethoxyflavone

The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml).IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2]In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. alb

Apigenin 7,4'-dimethyl ether is a dimethoxyflavone that is the 7,4'-dimethyl ether derivative of apigenin. It has a role as a plant metabolite. It is a dimethoxyflavone and a monohydroxyflavone. It derives from an apigenin.

Methylation of apigenin[0047] A solution of apigenin in MeOH was treated with ethereal diazomethane(CH2N2-Et2O) until the yellow color persisted. The reaction solution was stirred at room temperature for 30 min. Removal of the solvent under reduced pressure furnished a residue, which was purified by silica gel column chromatography (2:1 hexanes/EtOAc) to give compound 2 [Matsuda H, Morikawa T, Toguchida I5 Yoshikawa M: Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chemical & Pharmaceutical Bulletin 2002, 50(6):788-795.].General procedure: To a solution of the corresponding flavone (7) in dry acetonitrile (approx. 10mL per 1.0 mmol of flavone) at 0 C in an ice-bath under N2 atmosphere was added a portion of AlCl3 (2.5 equiv). The mixture was stirred at this temperature and then was allowed to warm up to room temperature and was refluxed for 1.5-2 h. At this point the conversion was checked by TLC, the reaction was allowed to cool and an additional portion of AlCl3 (2.5 equiv) was added slowly to the reaction mixture and was refluxed for an additional 1.5-2 h. After completion, after cooling the reaction mixture was poured into crushed ice and 6N HCl (30 mL per mmol flavone) was added and the suspension was extracted with CH2Cl2 (3 x 60 mL per mmol flavone), the combined organic phases were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated under vacuum; the residue was treated with hexane and filtered to yield the pure compounds.Testing of Activity of CBlOl Enantiomers[185] A new synthesis of CBlOl (as racemic mixture), carried out as shown on Figure 37 and described in X. Lei and J.A. Porco Jr., Org. Lett., 2004, 6: 795-798, which is incorporated herein by reference in its entirety, was performed and followed by separation of the enantiomeric (+) and (-) forms by chiral HLPC.

Molecular Weight:298.29
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:298.08412354
Monoisotopic Mass:298.08412354
Topological Polar Surface Area:65
Heavy Atom Count:22
Complexity:438
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes