新型查尔酮化合物3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮(FMC)衍生物的合成与体外抗氧化活性研究  

Synthesis and Antioxidant Activities of Novel Chalcone FMC and Its Analogues

作　　者：梁海[1,2] 向卓[2,3] 马天翔[2] 张学辉[2] 吴久鸿[2] 

机构地区：[1]安徽医科大学药学院,合肥230032 [2]解放军第306医院药学部,北京100101 [3]第四军医大学药学院,西安710032

出　　处：《中国药学杂志》2014年第21期1939-1944,共6页Chinese Pharmaceutical Journal

基　　金：国家自然科学基金面上项目资助课题(81072546)

摘　　要：目的设计、合成3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮(FMC)及其衍生物,并探讨其体外抗氧化活性。方法以2,4,6-三羟基苯乙酮为起始原料,经甲酰化、甲基化、O-甲基化,羟醛缩合4步反应合成了3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮以及6种新型3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮衍生物。通过建立体外清除1,1-二苯基-2-三硝基苯肼自由基模型和铁离子抗氧化能力(FRAP)总抗氧化模型,评价3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮以及其衍生物的体外抗氧化活性。结果合成了3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮及其衍生物,目标化合物的结构经MS,1H-NMR,13C-NMR确证。结论 3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮及其衍生物表现出良好的体外清除1,1-二苯基-2-三硝基苯肼自由基活性及总抗氧化能力,其中5f和5g活性优于3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮,说明在B环引入邻位二羟基结构对抗氧化活性的提高有很大贡献。OBJECTIVE To design and synthesize 3＇-formyl-4＇,6＇-dihydroxy-2＇-methoxy-5＇-methylchalcone（ FMC） and it analogues,and investigate their antioxidant activities in vitro.METHODS All the compounds were synthesized from 2,4,6-trihydroxyacetophenone through four-step reactions,ie,formylation,methylation,O-methylation,and aldol condensation.The antioxidative activities of FMC and its analogues were researched by DPPH and FRAP models.RESULTS FMC and its analogues were synthesized and confirmed by ^1H-NMR,^13C-NMR and MS spectra.Preliminary pharmacological test showed that FMC and its analogues had good scavenging DPPH radical activity in vitro and total antioxidant capacity,among which 5h and 5g were better than FMC.CONCLUSION Introducing O-dihydroxy into B-ring would significantly increases the antioxidant activity of the compounds.

关 键 词：查尔酮 3'-甲酰基-4' 6'-二羟基-2'-甲氧基-5'-甲基查尔酮(FMC) 合成 抗氧化活性 

分 类 号：R914.5[医药卫生—药物化学]