有机化学 ›› 2006, Vol. 26 ›› Issue (05): 685-689. 上一篇    下一篇

研究论文

新型查尔酮类化合物的合成及其生物活性研究

廖头根1,汪秋安*,1,方伟琴1,朱华结2   

  1. (1湖南大学化学化工学院 长沙 410082)
    (2中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室 昆明 650204)
  • 收稿日期:2005-07-21 修回日期:2006-11-02 出版日期:2006-04-28 发布日期:2006-04-28
  • 通讯作者: 汪秋安

Studies on the Synthesis of Novel Chalcone and Biological Activity

LIAO Tou-Gen1,WANG Qiu-An*,1,FANG Wei-Qin1,ZHU Hua-Jie2   

  1. (1 College of Chemical and Chemistry Engineering, Hunan University, Changsha 410082)
    (2 State Key Laboratory of Photochemistry and Plant Resource in West China, Kunming Institute of Botany,
    Chinese Academy of Sciences, Kunming 650204)
  • Received:2005-07-21 Revised:2006-11-02 Online:2006-04-28 Published:2006-04-28
  • Contact: WANG Qiu-An

以3,5-二羟基苯甲酸为原料, 分别经酯化、甲氧甲基保护或甲基化、酰肼化、氧化、醛酮缩合、脱保护基、O-法呢基化或O-异戊烯基化等步骤, 以5.6%~46%的总收率合成了8个未见文献报道的查尔酮类化合物1a1h, 产物通过1H NMR, 13C NMR, IR, MS进行了结构确证. 对所合成的目标化合物在3个标准活性筛选模型中进行了生物活性试验, 结果表明化合物1b在组织蛋白酶B (CAT-B)模型、化合物1e在细胞分离周期基因25表达的蛋白磷酸酶(CDC25)模型中表现出良好的活性.

关键词: 法呢氧基查尔酮, 异戊烯氧基查尔酮, 合成, 生物活性, 羟基查尔酮

Eight novel chalcone compounds 1a1h were synthesized by esterification, methoxymethyl protection or methylation, hydrazidation, oxidation, aldol condensation, deprotection, O-farnesylation or O-prenylation respectively using 3,5-dihydroxybenzoic acid as starting material in overall yield of 5.6%~46%. Their structures were confirmed by 1H NMR, 13C NMR, IR and MS spectra. Target compounds were screened with three international stan-dard models for biological activity. Results showed that 1b against model CAT-B and 1e against model CDC25 possessed the good inhibition activity.

Key words: prenyloxy chalcone, synthesis, farnesyloxy chalcone, biological activity, hydroxylated chalcone