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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (06): 884-889. 上一篇    下一篇

研究论文

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

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，李校堃1,2   

  1. 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
  • 收稿日期:2010-01-19 修回日期:2010-04-14 发布日期:2010-05-18
  • 通讯作者: 吴晓萍 E-mail:xp_wu2@yahoo.com.cn
  • 基金资助:

    在转录后水平上抑制炎症因子基因表达的药物筛选方法和构效关系研究;姜黄素衍生物的合成和抗肿瘤活性研究;姜黄素及其衍生物的硒化物合成和抗肿瘤活性研究

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

Wu Jianzhang1,2 Wang Cong1,3 Cai Yuepiao1 Yang Shulin2 Zheng Xiaoyong1 Qiu Peihong1 Peng Jing1 Wu Xiaoping*,1,3 Liang Guang*,1,2 Li Xiaokun1,2   

  1. 1 School of Pharmacy, Wenzhou Medicinal College, Wenzhou 325035) (2 Institute of Biotechnology, Nanjing University of Science and Technology, Nanjing 210094) (3 Institute of Tissue Transplantation and Immunology, Jinan University, Guangzhou 510632
  • Received:2010-01-19 Revised:2010-04-14 Published:2010-05-18
  • Contact: Wu Xiaoping E-mail:xp_wu2@yahoo.com.cn

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被引次数

11 | 6

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, 1H NMR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＝1.288 Mg/m3 , μ＝0.09 mm－1, F(000)＝324, 最终偏离因子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

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) ?, 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＝1.288 Mg/m3, μ＝0.09 mm－1, F(000)＝324, The final R＝0.047, wR＝0.112.

Key words: mono-carbonyl curcumin analogue, chalcone, synthesis, anti-tumor, antibacterial activity, crystal structure