有机化学 ›› 2015, Vol. 35 ›› Issue (1): 167-174.DOI: 10.6023/cjoc201407016 上一篇    下一篇

研究论文

新型吡咯类氨基酸缀合物的合成与抗肿瘤活性测定

李衍忠, 赵萍, 詹晓平, 刘增路, 毛振民   

  1. 上海交通大学药学院 上海 200240
  • 收稿日期:2014-07-10 修回日期:2014-08-20 出版日期:2015-01-25 发布日期:2014-09-12
  • 通讯作者: 毛振民 E-mail:zmmao@sjtu.edu.cn
  • 基金资助:

    国家“重大新药创制”科技重大专项(No. 2010ZX09401404-004)资助项目.

Synthesis and Cytotoxic Activities of Novel Amino Acid-Conjugates of Pyrrole Derivatives

Li Yanzhong, Zhao Ping, Zhan Xiaoping, Liu Zenglu, Mao Zhenmin   

  1. School of Pharmacy, Shanghai Jiaotong University, Shanghai 200240
  • Received:2014-07-10 Revised:2014-08-20 Online:2015-01-25 Published:2014-09-12
  • Supported by:

    Project supported by the National Science and Technology Major Special Drug Discovery (No. 2010ZX09401404-004).

以苯甲醛或3,4-二甲氧基苯甲醛为原料经Wittig-Horner反应、Van Leusen吡咯合成法、水解等多步反应, 设计并合成了16个未见文献报道的吡咯类氨基酸缀合物7a7p. 其结构经1H NMR, 13C NMR及HRMS确证. 采用噻唑蓝(MTT)法测试了目标化合物对MCF-7, MGC80-3, Hep G2, CT-26及HUVEC细胞的增殖抑制作用. 结果表明, 几乎所有化合物对人体正常细胞HUVEC无明显抑制作用, 化合物7a7h对Hep G2细胞株有一定的抑制活性, 化合物7i7p对MCF-7及MGC80-3较强的抑制活性. 其中化合物7o7p对MCF-7细胞株的抑制活性最强.

关键词: 吡咯, 氨基酸, 合成, 抗肿瘤活性

Sixteen novel amino acid-conjugates of pyrrole derivatives 7a7p were designed and synthesized using benzaldehyde or 3,4-dimethoxybenzaldehyde as raw materials. The compounds were synthesized via multi-step reaction including Wittig-Horner, Van Leusen and hydrolysis. The structures of all the target compounds were characterized by 1H NMR, 13C NMR and HRMS. Moreover, the cell proliferation inhibiting activities of the target compounds were evaluated against MCF-7, MGC80-3, Hep G2, CT-26 and HUVEC cell lines by thiazolyl blue tetrazolium bromide (MTT) method. The result indicated that most of the compounds had no significant inhibitory effect against normal human cell HUVEC. However compounds 7a7h showed significant inhibitory effect against Hep G2, compounds 7i7p showed stronger inhibitory effect against MCF-7 and MGC 80-3, and compound 7o7p exhibited the strongest inhibitory activity against MCF-7 in all of the compounds.

Key words: pyrrole, amino acid, synthesis, cytotoxic activities