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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 (CC BY 3.0).

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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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