Abstract
A series of 6-halo-3-hydroxyphenylcoumarins (resveratrol-coumarins hybrid derivatives) was synthesized in good yields by a Perkin reaction followed by hydrolysis. The new compounds were evaluated for their vasorelaxant activity in intact rat aorta rings pre-contracted with phenylephrine (PE), as well as for their inhibitory effects on platelet aggregation induced by thrombin in washed human platelets. These compounds concentration-dependently relaxed vascular smooth muscle and some of them showed a platelet antiaggregatory activity that was up to thirty times higher than that shown by trans-resveratrol and some other previously synthesized derivatives.
Highlights
Coumarins are a large family of compounds of natural and synthetic origin that show numerous biological activities, including cardiovascular properties [1]
With the aim of improving the vasorelaxant and platelet antiaggregatory activities of resveratrol-coumarin hybrids and establishing a relationship between the structure and activity for this type of compounds we have studied the effects of substitution on the 3-arylcoumarin moiety with groups showing different steric and electronics effects
In this paper we report the synthesis and evaluation of a new series of 3-arylcoumarins in which the hydroxy group in the 6 position has been changed for a halogen group, and different positions of hydroxyl group in 3-phenyl ring were explored
Summary
Coumarins (or benzopyrones) are a large family of compounds of natural and synthetic origin that show numerous biological activities, including cardiovascular properties [1]. It is abundant in the skin of the grapes and it is present in higher concentrations in red than in white wines. Trans-Resveratrol has shown a number of biological activities, including protection against coronary heart disease, as a result of different effects: significant antioxidant activity, modulation of lipoprotein metabolism, and vasodilatatory and platelet antiaggregatory properties [5,6,7,8]. Because of their similar characteristics, it was of interest to design and synthesize hybrids that incorporate the nucleus of the coumarins and resveratrol molecules. In this paper we report the synthesis and evaluation of a new series of 3-arylcoumarins in which the hydroxy group in the 6 position has been changed for a halogen group, and different positions of hydroxyl group in 3-phenyl ring were explored
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