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

Xiaowu Dong, Yanming Wang, Tao Liu, Peng Wu, Jiadi Gao, Jianchao Xu, Bo Yang, Yongzhou Hu

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A series of 2-(2-diethylamino)-ethoxychalcone and 6-prenyl(or its isomers)-flavanones 10a, b and 11a-g were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pretreated with 1 mu M 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.
Original languageEnglish
Issue number10
Pages (from-to)8257-8272
Number of pages16
Publication statusPublished - 2011
Externally publishedYes

Bibliographical note

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.


  • Organic Chemistry
  • Molecular descriptors
  • QSAR
  • Vasorelaxant agents
  • 2 (2 diethylamino) ethoxychalcone
  • 2-(2-diethylamino)-ethoxychalcone
  • Chalcone derivative
  • Ethylamine
  • Vasodilator agents
  • Animal
  • Aorta
  • Cell culture
  • Chemical structure
  • Drug effect
  • Metabolism
  • Organ culture technique
  • Quantitative structure activity relation
  • Synthesis
  • Animals
  • Cells, Cultured
  • Chalcones
  • Ethylamines
  • Molecular Structure
  • Organ Culture Techniques
  • Quantitative Structure-Activity Relationship
  • Rats
  • Vasodilator Agents
  • Chemistry
  • Flavonoids
  • erm-mlr
  • Mesenteric-artery
  • Prenylflavonoid
  • Polyphenols
  • Descriptores
  • QSPR


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