2-二茂铁基乙醇的合成及其抗肿瘤活性
DOI:
作者:
作者单位:

作者简介:

通讯作者:

中图分类号:

R914

基金项目:

陕西省自然科学基础研究计划


Synthesis and Anti-tumor Activity Evaluation of 2-Ferrocenylethanol
Author:
Affiliation:

Fund Project:

  • 摘要
  • |
  • 图/表
  • |
  • 访问统计
  • |
  • 参考文献
  • |
  • 相似文献
  • |
  • 引证文献
  • |
  • 资源附件
  • |
  • 文章评论
    摘要:

    以二茂铁为原料,首先与乙酸酐发生Friedel-Crafts酰基化反应制得乙酰基二茂铁,接着通过Willgerodt-Kindler反应制得二茂铁乙酸,再经过还原反应得到了目标化合物2-二茂铁基乙醇。并在二茂铁乙酸还原成2-二茂铁基乙醇的反应中,探讨了不同反应条件对产物收率的影响。确定了最佳还原条件为:还原剂为氢化铝锂、物料比n (氢化铝锂):n (二茂铁乙酸)为8 : 1,溶剂为四氢呋喃,反应温度为25 C,反应时间为24 h,2-二茂铁基乙醇的收率为82 %。随后,初步的活性测试结果表明,2-二茂铁基乙醇对人乳腺癌细胞MCF-7和MDA-MB-231、人肝癌细胞HepG2、人宫颈癌细胞HeLa均有明显地抑制活性,其半数抑制浓度(IC50)值分别为17.4、12.9、20.7、24.6 μmol/L;此外,2-二茂铁基乙醇对正常的MCF-10A细胞没有毒性,而阳性对照药物5-FU展现出了一定的毒性。

    Abstract:

    Hydroxyl ferrocene is an important intermediate for the synthesis of ferrocene derivatives. There are several methods for the synthesis of 1-ferrocenylethanol whereas the synthesis of 2-ferrocenylethanol is rarely reported. In this work, the target compound 2-ferrocenylethanol was synthesized through a three-step reaction: first, acetyl ferrocene was prepared from ferrocene and acetic anhydride by Friedel-Grafts acylation reaction, then ferrocenylacetic acid was synthesized by Willgerodt-Kindler reaction, followed 2-ferrocene ethanol was obtained by reduction reaction. The effects of different reaction conditions on the yield of 2-ferrocenylethanol from ferrocenylacetic acid were studied. The optimum reduction conditions were determined as follows: the reducing agent was lithium aluminum hydride; n (lithium aluminum hydride): n (ferrocenylacetic acid) was 8 : 1; the solvent was tetrahydrofuran; the reaction temperature was 25C; the reaction time was 24 h, and the yield of 2-ferrocenylethanol was 82 %. Subsequently, anti-tumor activities of 2-ferrocenylethanol were evaluated against human breast cancer MCF-7 and MDA-MB-231, human liver cancer HepG2, human cervical cancer HeLa cell lines in vitro. The preliminary activity test results showed that 2-ferrocenylethanol showed obvious inhibitory activities, against MCF-7, MDA-MB-231, HepG2 and HeLa, and its half inhibitory concentration (IC50) value was 17.4, 12.9, 20.7, 24.6 μmol/L, respectively. Additionally, 2-ferrocenylethanol was nontoxic to normal MCF-10A cells, while the positive control drug 5- FU exhibited essential toxicity.

    参考文献
    相似文献
    引证文献
引用本文

问娟娟,刘斌.2-二茂铁基乙醇的合成及其抗肿瘤活性[J].精细化工,2020,37(11):

复制
分享
文章指标
  • 点击次数:
  • 下载次数:
  • HTML阅读次数:
  • 引用次数:
历史
  • 收稿日期:2020-05-27
  • 最后修改日期:2020-07-15
  • 录用日期:2020-07-17
  • 在线发布日期: 2020-09-25
  • 出版日期: