二苯乙烯衍生物的合成及其抗真菌活性测定  

Synthesis and antifungal activity of stilbene derivatives

作　　者：王岁 杨海进 徐秀丽[2] 刘梅[3] 谌晨 温鸿亮 WANG Sui;YANG Haijin;XU Xiuli;LIU Mei;SHEN Chen;WEN Hongliang(School of Chemistry and Chemical Engineering,Beijing Institution of Technology,Beijing 102488,China;College of Marine Science and Technology,China University of Geosciences,Beijing 100083,China;Institute of Microbiology,Chinese Academy of Sciences,Beijing 100101,China)

机构地区：[1]北京理工大学化学与化工学院,北京102488 [2]中国地质大学海洋学院,北京100083 [3]中国科学院微生物研究所,北京100101

出　　处：《沈阳药科大学学报》2020年第3期223-230,共8页Journal of Shenyang Pharmaceutical University

摘　　要：目的设计合成二苯乙烯衍生物,并研究其抗真菌活性和构效关系。方法以紫檀芪为先导化合物,分别保持其A环和B环的结构不变,设计并合成了28个二苯乙烯衍生物,所得产物经1H-NMR和MS验证了结构。参照CLSI(Clinical and Laboratory Standards Institute)M27A方案,以两性霉素B为阳性对照,DMSO为阴性对照,测定了目标化合物对白色念珠菌属Candida albicans SC-5314、Candida albicans 17#和Candida albicans G5的体外抗真菌活性。结果部分化合物具有良好的抗真菌活性,其中(E)-3,5-二甲氧基-2′-羟基二苯乙烯(PS-18)对3种菌株的最小抑菌浓度分别为3.125、6.25、6.25 mg·L-1,优于紫檀芪。结论当保持紫檀芪A环结构不变,改变B环结构得到的化合物抗真菌活性差异较大。当B环的酚羟基在2′位时,化合物PS-18表现出比紫檀芪更强的抗真菌活性;而当紫檀芪B环2′位增加一个甲基后,化合物PS-16仅表现出微弱的抗真菌活性。Objective To study the antifungal activity and structure-activity relationship of stilbene derivatives.Methods The pterostilbene was used as the lead compound and 28 stilbene derivatives were designed and synthesized.The obtained product was verified by 1H-NMR and MS.Referring to the CLSI(Clinical and Laboratory Standards Institute)M27 A protocol,amphotericin B was used as a positive control and DMSO was used as a negative control.The in vitro antifungal activity of the target and the substance was evaluated by Candida albicans SC5314,Candida albicans 17#and Candida albicans G5.Results It indicated that some compounds had good antifungal activity,and the minimum inhibitory concentration of(E)-3,5-dimethoxy-2′-hydroxystilbene(PS-18)against the three strains was 3.125,6.25 and 6.25 mg·L-1 which are superior to pterostilbene.Conclusion When the structure of the A ring of the pterostilbene is kept unchanged,the antifungal activity of the compound obtained by changing the B ring structure is quite different.When the phenolic hydroxyl group of the B ring is at the 2′position,the compound PS-18 exhibits stronger antifungal activity than the pterostilbene;and when the 2′position of the B ring of the pteronoid is increased by a methyl group,the compound PS-16 only shows weak antifungal activity.

关 键 词：二苯乙烯 紫檀芪 抗真菌活性 

分 类 号：R914[医药卫生—药物化学] R96[医药卫生—药学]