Journal article
Flavonoids as Vasorelaxant Agents: Synthesis, Biological Evaluation and Quantitative Structure Activities Relationship (QSAR) Studies
ZJU-ENS Joint Laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, China1
Institute of Pharmacology & Toxicology, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, China2
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 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.
| Language: | Undetermined |
|---|---|
| Publisher: | MDPI |
| Year: | 2011 |
| Pages: | 8257-8272 |
| ISSN: | 14203049 |
| Types: | Journal article |
| DOI: | 10.3390/molecules16108257 |
2-(2-diethylamino)-ethoxychalcone Animals Aorta Cells, Cultured Chalcones Ethylamines Flavonoids Molecular Structure Organ Culture Techniques Organic chemistry QD241-441 Quantitative Structure-Activity Relationship Rats Vasodilator Agents erm-mlr flavonoids molecular descriptors qsar vasorelaxant agents
