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Molecules 2011, 16(10), 8257-8272; doi:10.3390/molecules16108257
Article

Flavonoids as Vasorelaxant Agents: Synthesis, Biological Evaluation and Quantitative Structure Activities Relationship (QSAR) Studies

1, 1, 1, 1, 1, 1, 2 and 1,*
1 ZJU-ENS Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, China 2 Institute of Pharmacology & Toxicology, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, China
* Author to whom correspondence should be addressed.
Received: 29 July 2011 / Revised: 14 September 2011 / Accepted: 16 September 2011 / Published: 28 September 2011
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Abstract

A series of 2-(2-diethylamino)-ethoxychalcone and 6-prenyl(or its isomers)-flavanones 10a,b and 11ag were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pretreated with 1 μM phenylephrine (PE). Several compounds showed potent vasorelaxant activities. Compound 10a (EC50 = 7.6 μM, Emax = 93.1%), the most potent one, would be a promising structural template for development of novel and more efficient vasodilators. Further, 2D-QSAR analysis of compounds 10a,b and 11c-e as well as thirty previously synthesized flavonoids 1-3 and 12-38 using Enhanced Replacement Method-Multiple Linear Regression (ERM-MLR) was further performed based on an optimal set of molecular descriptors (H5m, SIC2, DISPe, Mor03u and L3m), leading to a reliable model with good predictive ability (Rtrain2 = 0.839, Qloo2 = 0.733 and Rtest2 = 0.804). The results provide good insights into the structure- activity relationships of the target compounds.
Keywords: flavonoids; molecular descriptors; vasorelaxant agents; qsar; erm-mlr flavonoids; molecular descriptors; vasorelaxant agents; qsar; erm-mlr
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Dong, X.; Wang, Y.; Liu, T.; Wu, P.; Gao, J.; Xu, J.; Yang, B.; Hu, Y. Flavonoids as Vasorelaxant Agents: Synthesis, Biological Evaluation and Quantitative Structure Activities Relationship (QSAR) Studies. Molecules 2011, 16, 8257-8272.

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