首页|(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

(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

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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Na2SO4介质中经固相研磨合成产物(1),产物结构经1H NMR和ESI-MS表征.优化并确定该反应的适宜条件为:无水Na2SO4用量为nNa2SO4∶n2=0.5∶1、KOH用量为nKOH∶n2=1.2∶1、物料摩尔比n3∶n2=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(IC50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.
Synthesis and in vitro antitumor activity of(E)-1,3-diferrocenylprop-2-en-1-one
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 nNa2SO4∶n2=0.5∶1,the amount of potassium hydroxide is nKOH∶n2=1.2∶1,the molar ratio of material is n3∶n2=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(IC50 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.

ferrocenechalconesolid-phase synthesisantitumor activity

杨晓凤、赵梅梅、高艳蓉、杜漠、唐文强

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陕西国际商贸学院医药学院,陕西咸阳 712046

陕西国际商贸学院高职学院,陕西咸阳 712046

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

二茂铁 查尔酮 固相合成 抗肿瘤活性

陕西省教育厅专项科学研究计划(2022)陕西国际商贸学院中药药效物质研究创新团队项目咸阳市分子影像与药物合成重点实验室项目

22JK0280SSY18TD022021QXNL-PT-0008

2024

化学工程师
黑龙江省化工研究院

化学工程师

CSTPCD
影响因子:0.243
ISSN:1002-1124
年,卷(期):2024.38(8)