文章摘要
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):
2-二茂铁基乙醇的合成及其抗肿瘤活性
Synthesis and Anti-tumor Activity Evaluation of 2-Ferrocenylethanol
投稿时间:2020-05-27  修订日期:2020-07-15
DOI:
中文关键词: 2-二茂铁基乙醇  Willgerodt-Kindler 反应  合成  抗肿瘤活性
英文关键词: 2-ferrocenylethanol  Willgerodt-Kindler reaction  synthesis  anti-tumor activity
基金项目:陕西省自然科学基础研究计划
作者单位E-mail
问娟娟 陕西国际商贸学院 wjj1596249227@163.com 
刘斌 陕西国际商贸学院 lb125lb@163.com 
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中文摘要:
      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。
英文摘要:
      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.
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