(E)-1,3-二茂铁基丙-2-烯-1-酮的合成及体外抗肿瘤活性研究  

Synthesis and in vitro antitumor activity of (E)-1,3-diferrocenylprop-2-en-1-one

作　　者：杨晓凤[1] 赵梅梅 高艳蓉 杜漠 唐文强 YANG Xiao-feng;ZHAO Mei-mei;GAO Yan-rong;DU Mo;TANG Wen-qiang(School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xianyang 712046,China;Higher Vocational College,Shaanxi Institute of International Trade&Commerce,Xianyang 712046,China;Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis,Shaanxi Institute of International Trade&Commerce,Xianyang 712046,China)

机构地区：[1]陕西国际商贸学院医药学院,陕西咸阳712046 [2]陕西国际商贸学院高职学院,陕西咸阳712046 [3]陕西国际商贸学院咸阳市分子影像与药物合成重点实验室,陕西咸阳712046

出　　处：《化学工程师》2024年第8期5-8,共4页Chemical Engineer

基　　金：陕西省教育厅2022年度专项科学研究计划项目(22JK0280);陕西国际商贸学院“中药药效物质研究”创新团队资助项目(SSY18TD02);咸阳市分子影像与药物合成重点实验室项目(2021QXNL-PT-0008)。

摘　　要：报道一种结构新颖的二茂铁基查尔酮衍生物——(E)-1,3-二茂铁基丙-2-烯-1-酮(1)的合成及体外抗肿瘤活性研究。在KOH碱性条件下,乙酰基二茂铁(2)与二茂铁甲醛(3)在无水Na_(2)SO_(4)介质中经固相研磨合成产物(1),产物结构经^(1)H NMR和ESI-MS表征。优化并确定该反应的适宜条件为:无水Na_(2)SO_(4)用量为n_(Na2)SO_(4)∶n_(2)=0.5∶1、KOH用量为n_(KOH)∶n_(2)=1.2∶1、物料摩尔比n_(3)∶n_(2)=2.2∶1。在该条件下,产物(1)的收率达到69.6%。最后,采用MTT法测试了产物(1)对荷尔蒙依赖性乳腺癌MCF-7和三阴性乳腺癌MDA-MB-231的体外抑制活性。结果表明,产物(1)对MCF-7和MDA-MB-231细胞均有一定的抑制活性(IC_(50)值分别为29.03和28.23μM·L^(-1)),但对正常的乳腺上皮细胞MCF-10A没有明显的抑制活性。该研究结果将为二茂铁基查尔酮类抗肿瘤分子的开发提供参考。A novel ferrocenyl chalcone derivative(E)-1,3-diferrocenylprop-2-en-1-one(1) was synthesized and its antitumor activity in vitro was studied.The product(1) was synthesized by solid-phase grinding of acetylferrocene(2) and ferrocenecarboxaldehyde(3) in the presence of potassium hydroxide and anhydrous sodium sulfate.The optimum reaction conditions are as follows:the dosage of anhydrous sodium sulfate is n_(Na_(2)SO_4)∶n_(2)=0.5∶1,the amount of potassium hydroxide is n_(KOH)∶n_(2)=1.2∶1,the molar ratio of material is n_(3)∶n_(2)=2.2∶1.Under these conditions,the yield of the product was 69.6%.At last,MTT assay was used to test the in vitro inhibitory activity of the product(1) against hormone-dependent breast cancer MCF-7 and triple-negative breast cancer MDA-MB-231.The results showed that the product(1) had certain inhibitory activity on MCF-7 and MDA-MB-231 cells(IC_(50) were 29.03 and 28.23μM·L^(-1),respectively),however,the product(1) had no significant inhibitory activity against normal mammary epithelial cells MCF-10A.The results will provide references for the development of ferrocenylchalcone anti-tumor molecules.

关 键 词：二茂铁 查尔酮 固相合成 抗肿瘤活性 

分 类 号：TQ463[化学工程—制药化工]