单羰基姜黄素衍生物的合成、晶体结构、体外抗菌及抗肿瘤活性研究  

Synthesis,Crystal Structure,Antibacterial and Anti-tumor Properties of Mono-carbonyl Analogues of Curcumin

作　　者：吴建章[1,2] 王聪[1,3] 蔡跃飘[1] 杨树林[2] 郑晓咏[1] 仇佩虹[1] 彭景[1] 吴晓萍[1,3] 梁广[1,2] 李李堃 

机构地区：[1]温州医学院药学院,温州325035 [2]南京理工大学化工学院,南京210094 [3]暨南大学组织移植与免疫实验中心,广州510632

出　　处：《有机化学》2010年第6期884-889,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20802054);浙江省教育厅(No.20070992);温州市科技局(No.Y20080016)资助项目

摘　　要：以姜黄素为先导化合物合成了两个对称的单羰基姜黄素类似物和五个查尔酮类单羰基姜黄素类似物,结构经IR,1HNMR及ESI-MS确认,用11种临床常用耐药株对其进行了体外抗菌活性筛选,同时采用MTT法测定了它们对3种人体肿瘤细胞株的细胞毒活性.其中化合物A5的体外抗肿瘤活性与姜黄素相当,并且A5对部分临床耐药菌也有一定的抑菌活性.通过单晶培养得到了A5的晶体结构,经测定表明其结构属于正交晶系,空间群Fdd2.晶胞参数a=26.085(3),b=28.248(3),c=7.9615(9),α=90.00°,β=90.00°,γ=90.00°,V=5866.4(12)3,Z=16,DX=1.288Mg/m3,μ=0.09mm-1,F(000)=324,最终偏离因子R=0.047,wR=0.112.Two symmetry and five asymmetry mono-carbonyl analogues were synthesized with curcumin as leading compound.Their structures were characterized by IR,MS and ^1H NMR techiniques.Their antibacterial activities in vitro were tested using 11 drug-resistant strains isolated in clinical.The cytotoxicity activities in vitro were evaluated by MTT assay using 3 human cancer cell lines.Compound A5 exhibited a comparable antitumor activity with curcumin and showed high antibacterial activity.Due to the good bioactivities,single-crystal of A5 was cultured and its structure was determined using single-crystal X-ray diffraction.The crystal structure of compound A5 is orthorhombic system,space group Fdd2,with cell dimensions of a=26.085（3）A°,b=28.248（3）A°,c=7.9615（9）A°,α=90.00°,β=90.00°,γ=90.00°,V=5866.4（12）A°^3,Z=16,DX=1.288 Mg/m3,μ=0.09 mm^-1,F（000）=324,The final R=0.047,wR=0.112.

关 键 词：单羰基姜黄素衍生物 查尔酮 合成 抗肿瘤 抗菌活性 晶体结构 

分 类 号：R284[医药卫生—中药学]