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有机化学 ›› 2004, Vol. 24 ›› Issue (7): 783-787. 上一篇    下一篇

研究论文

哌嗪取代卟啉的合成、表征及其抗癌活性

李和平*,a,b, 郭灿城c, 阮建明a, 黄伯云a   

  1. a中南大学粉末冶金国家重点实验室 长沙 410083
    b长沙电力学院化学系 长沙 410077
    c湖南大学化学化工学院 长沙 410082
  • 收稿日期:2003-06-23 修回日期:2003-11-25 接受日期:2004-02-09 发布日期:2022-09-20
  • 通讯作者: *E-mail: lihepinghn@sohu.com; Tel.: 0731-8876644
  • 基金资助:
    国家自然科学基金(No. 20142003)、湖南省教育厅青年基金(No. 02B022)资助项目

Synthesis, Characterization and Anticancer Activity of Piperazine Substituted Porphyrins

LI, He-Ping*,a,b, GUO, Can-Chengc, RUAN, Jian-Minga, HUANG, Bai-Yuna   

  1. a State Key Laboratory for Powder Metallurgy, Central South University, Changsha 410083
    b Department of Chemistry, Changsha University of Electric Power, Changsha 410077
    c College of Chemistry & Chemical Engineering, Hunan University, Changsha 410082
  • Received:2003-06-23 Revised:2003-11-25 Accepted:2004-02-09 Published:2022-09-20

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设计并合成了6个具有抗癌活性的哌嗪取代卟啉化合物,分别为5,10,15,20-四[4-(4′-乙基哌嗪基)苯基]卟啉(TEPPH2, 8a), 5,10,15,20-四[4-(4′-丁基哌嗪基)苯基]卟啉(TBPPH2, 8b), 5,10,15,20-四[4-(4′-庚基哌嗪基)苯基]卟啉(THPPH2, 8c), 5,10,15,20-四[4-(4′-苯基哌嗪基)苯基]卟啉(TPhPPH2, 8d), 5-[4-(4′-乙基哌嗪基)苯基]-10,15,20-三苯基卟啉(EPTPPH2, 8e)和5-[4-(4′-丁基哌嗪基)苯基]-10,15,20-三苯基卟啉(BPTPPH2, 8f).这些卟啉化合物都由取代苯甲醛与吡咯缩合而成,每一个卟啉分子中含有一个或四个具有抗癌活性的取代哌嗪结构,结构经元素分析,MS, 1H NMR, IR和UV-vis等表征.初步的生物活性研究表明,这些化合物具有一定的抗癌活性,因而在医学上可能具有潜在应用前景.

关键词: 卟啉, 哌嗪, 合成, 抗癌活性

A molecular design strategy was outlined for the synthesis of porphyrin-containing anticancer drugs. A series of six porphyrin monomers, 5,10,15,20-tetra[4-(4′-ethylpiperazinyl)phenyl]porphyrin (TEPPH2, 8a), 5,10,15,20-tetra[4-(4′-butylpiperazinyl)phenyl]porphyrin (TBPPH2, 8b), 5,10,15,20-tetra[4-(4′-heptylpiperazinyl)-phenyl]porphyrin (THPPH2, 8c), 5,10,15,20-tetra[4-(4′-phenylpiperazinyl)phenyl]porphyrin (TPhPPH2, 8d), 5-[4-(4′-ethylpiperazinyl)phenyl]-10,15,20-triphenylporphyrin (EPTPPH2, 8e) and 5-[4-(4′-butylpiperazinyl)-phenyl]-10,15,20-triphenylporphyrin (BPTPPH2, 8f), have been prepared by the direct condensation of substituted benzaldehydes with pyrrole. Each porphyrin bears one or four substituted piperazine moieties that have been used as drugs. Their structures were characterized by elemental analysis, MS, 1HNMR, IR and UV-vis spectra. The preliminary investigation of anticancer activity of these porphyrins showed that the porphyrins might have potential application in medicine owing to their special biological activity.

Key words: porphyrin, piperazine, synthesis, anticancer activity