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Citation: . Synthesis of Bromo-Methoxyl Benzophenone Imidazole Compounds and Their Protective Activities Against Hydrogen Peroxide Induced Injury in EA.hy 926 Cells[J]. Chinese Journal of Applied Chemistry, ;2017, 34(7): 783-788. doi: 10.11944/j.issn.1000-0518.2017.07.160440 shu

Synthesis of Bromo-Methoxyl Benzophenone Imidazole Compounds and Their Protective Activities Against Hydrogen Peroxide Induced Injury in EA.hy 926 Cells

Received Date: 3 November 2016
Revised Date: 15 December 2016
Accepted Date: 23 January 2017

Fund Project: Ph.D. Funded Start-up Funding of Shanxi Medical University B03201213Shanxi Province Coal-based Key Scientific and Technological Projects in 2014 MJH2014-14the National High Technology Research and Development Plan("863" plan) 2013AA092903the National Natural Science Foundation of China 81473100

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To introduce the imidazole ring to the bromo-methoxyl benzophenone structures and find the target compounds with high protective activity on vacular endothelium cells, eight novel bromo-methoxyl benzophenone imidazole compounds were synthesized using 5-bromo-2-methylbenzoic acid as starting material via following reactions:acylating chlorination, Friedel acylation, bromination, radical substitution with N-bromosuccinimide(NBS) and nucleophilic substitution with substituted imidazoles. The structures of the target compounds were confirmed by proton and carbon nuclear magnetic resonance spectroscopy(¹H and ¹³C NMR) and high resolution mass spectrometry(HRMS). Additionally, the protective effects of the target compounds against H₂O₂-induced EA.hy 926 cells injury were evaluated by methylthiazolyldiphenyl-tetrazolium bromide(MTT) assay and their structure-activity relationships were also preliminarily discussed. The in vitro results show that target compounds 6a, 6g and 6h exhibit significant cytoprotective activities and their half maximal inhibitory concentration(EC₅₀) values are 1.9, 4.0 and 3.2 μmol/L, respectively, superior to the positive control Quercetin(EC₅₀≈18 μmol/L). These results also suggest the potential application prospect of target compounds in the treatment of cardiovascular diseases.
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