Synthesis, biological evaluation, and molecular docking of dihydroflavonol derivatives as anti-inflammatory agents

被引：0
作者：
Yuanhang Xiang
Chunling Hu
Yuejie Zhang
Xiaochuan Ye
机构：
[1] Hubei University of Traditional Chinese Medicine,Key Laboratory of Chinese Medicine Chemistry and Chinese Herbal Compound of Hubei Province
来源：
Medicinal Chemistry Research | 2019年 / 28卷
关键词：
Inflammation; Dihydroflavonol; Molecular docking; Cytokine;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A series of dihydroflavonol derivatives (4a–4l) were synthesized from chalcones via classical Algar–Flynn–Oyamada (AFO) reaction and characterized on the basis of spectroscopic analyses. All synthesized compounds were evaluated for their inhibitory activity against the pro-inflammatory-inducible TNF-alpha, IL-1beta, and IL-6 in lipopolysaccharide (LPS)-stimulated RAW 264.7 cell lines and showed various efficiency. Furthermore, compounds 4d and 4k were selected to examine their in vivo anti-inflammatory activity by using two classical models. Herein compound 4k showed maximum anti-inflammatory activity of 32.98% inhibition in mice ear-swelling model and 40.06% inhibition at the 2 h intervals in rat paw edema model in comparison to the two references: aspirin and meloxicam. Similar effect was observed at a lower dose. In addition, the compound 4k was docked against cyclooxygenases-2 to validate the attained pharmacological data and provide understandable evidence for the observed anti-inflammatory activity.
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页码：863 / 872
页数：9
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[1]  
Ayoub IM(2018)Probing the antiallergic and anti-inflammatory activity of biflavonoids and dihydroflavonols from dietes bicolor J Nat Prod 81 243-253
[2]  
Korinek M(2015)Suppression of inflammation and arthritis by orally administrated cardiotoxin from Naja naja atra Evid-Based Complement Altern Med 2015 387094-270
[3]  
Hwang TL(2018)Inflammation-targeted vascular nanomedicine Nat Biomed Eng 2 269-10
[4]  
Chen BH(2015)Kaempferol and inflammation: from chemistry to medicine Pharmacol Res 99 1-53
[5]  
Chang FR(2018)Kidney protection effects of dihydroquercetin on diabetic nephropathy through suppressing ROS and NLRP3 inflammasome Phytomedicine 41 45-205
[6]  
El-Shazly M(2018)Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives Med Chem Res 27 194-6929
[7]  
Singab ANB(2015)Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: synthesis and the structure–activity relationship Biorg Med Chem 23 6922-1785
[8]  
Chen CX(2016)Antimicrobial dihydroflavonol from Sudanese Int J Adv Res 4 1779-2786
[9]  
Chen JY(2011) Muell. Arg. (Euphorbiaceae) seeds J Chem Inf Model 51 2778-606
[10]  
Kou JQ(2017)LigPlot+: multiple ligand–protein interaction diagrams for drug discovery Bioorg Med Chem Lett 27 602-2791
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