Discovery of Water-Soluble Antioxidant Flavonols without Vasorelaxant Activity
Suwan Yap, Karen J Loft, Owen L Woodman, Spencer J Williams
CHEMMEDCHEM | WILEY-V C H VERLAG GMBH | Published : 2008
3',4'-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that can decrease ischaemia/reperfusion injury in the heart. DiOHF exhibits antioxidant and vasorelaxant properties that are thought to underlie its cardioprotective activity. A major limitation to its use for the treatment or prevention of cardiovascular disease is its poor water solubility, preventing intravenous administration at the required dosage. In this study, three novel flavonols were synthesised that bear an ionisable succinamic acid substituent at the 6-position of the A ring with zero, one, or two hydroxy groups on the B ring. The ionised compounds possess improved aqueous solubility, dissolving at concentrations up ..View full abstract
This research was supported by grants from the Australian Research Council and the Shepherd Foundation. S.Y is supported by an Endeavour International Postgraduate Research Scholarship. C. X. Qin is thanked for practical improvements to the synthesis of 1.