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Synthesis and Vasorelaxant and Platelet Antiaggregatory Activities of a New Series of 6-Halo-3-phenylcoumarins†
Chemistry Department, Faculty of Sciences, University Porto, 4169-007 Porto, Portugal
Dipartimento Farmaco Chimico Tecnologico, Universita degli Studi di Cagliari, Via Ospedale 72, 09124 Cagliari, Italy
Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain
Department of Pharmacology, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain
† In memory of Prof. Francisco Orallo.
* Author to whom correspondence should be addressed.
Received: 4 December 2009; in revised form: 21 December 2009 / Accepted: 23 December 2009 / Published: 12 January 2010
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.
Keywords: resveratrol; coumarin; vasorelaxant; platelet antiaggregatory activity
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Quezada, E.; Delogu, G.; Picciau, C.; Santana, L.; Podda, G.; Borges, F.; García-Morales, V.; Viña, D.; Orallo, F. Synthesis and Vasorelaxant and Platelet Antiaggregatory Activities of a New Series of 6-Halo-3-phenylcoumarins. Molecules 2010, 15, 270-279.
Quezada E, Delogu G, Picciau C, Santana L, Podda G, Borges F, García-Morales V, Viña D, Orallo F. Synthesis and Vasorelaxant and Platelet Antiaggregatory Activities of a New Series of 6-Halo-3-phenylcoumarins. Molecules. 2010; 15(1):270-279.
Quezada, Elías; Delogu, Giovanna; Picciau, Carmen; Santana, Lourdes; Podda, Gianni; Borges, Fernanda; García-Morales, Verónica; Viña, Dolores; Orallo, Francisco. 2010. "Synthesis and Vasorelaxant and Platelet Antiaggregatory Activities of a New Series of 6-Halo-3-phenylcoumarins." Molecules 15, no. 1: 270-279.