Dupont R, Goossens J F, Cotelle N, Vrielynck L, Vezin H, Hénichart J P, Cotelle P
Laboratoire de Chimie Organique et Macromoléculaire, UPRESA CNRS 8009, Villeneuve d'Ascq, France.
Bioorg Med Chem. 2001 Feb;9(2):229-35. doi: 10.1016/s0968-0896(00)00258-3.
Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors.
