Synthesis and antiproliferative evaluation of novel chrysin selenocyanates

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC Synthetic Communications Pub Date : 2025-02-01 Epub Date: 2024-12-27 DOI:10.1080/00397911.2024.2445860

Zhiping Liu , Lijie Che , Yunlong Ban , Maixia Liu , Xiyan Tang , Yanmin Huang , Jianguo Cui , Chunfang Gan

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Abstract

Selenocyano fragments with distinct structural characteristics were successfully incorporated into the 5- and 7-positions of chrysin via etherification and esterification of its hydroxyl groups. Eleven novel chrysin selenocyanates were synthesized, and their structures characterized by NMR and HRMS. The activities of all compounds were evaluated against human cervical cancer cell lines HeLa, ovarian cancer cell lines SKOV-3, and breast carcinoma cell lines MCF-7 using MTT assays. Results indicated that esterified chrysin derivatives significantly inhibited HeLa cells, while alkylated chrysin ethers showed notable activity against SKOV-3 and MCF-7 cells. Compounds 5c and 5e exhibited the strongest inhibitory effects on SKOV-3 cells, with IC₅₀ values of 2.27 ± 0.19 μM and 2.51 ± 0.33 μM, respectively. The introduction of diselenocyanate at both the 5- and 7-positions demonstrated superior inhibitory activity compared to a single selenocyanate at the 7-position alone. The findings may aid in designing novel chemotherapeutic drugs.

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新型硒氰酸菊素的合成及抗增殖活性评价

具有明显结构特征的硒基氰酸酯片段通过其羟基的醚化和酯化作用成功地结合到菊花素的5位和7位上。合成了11种新型的菊花素硒氰酸酯，并通过NMR和HRMS对其结构进行了表征。采用MTT法测定了各化合物对人宫颈癌细胞株HeLa、卵巢癌细胞株SKOV-3和乳腺癌细胞株MCF-7的活性。结果表明，酯化的菊花素衍生物对HeLa细胞有明显的抑制作用，而烷基化的菊花素醚对SKOV-3和MCF-7细胞有明显的抑制作用。化合物5c和5e对SKOV-3细胞的抑制作用最强，IC50值分别为2.27±0.19 μM和2.51±0.33 μM。在5位和7位引入二硒氰酸酯比在7位单独引入硒氰酸酯表现出更好的抑制活性。这一发现可能有助于设计新的化疗药物。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.