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 DOI:10.1080/00397911.2024.2445860

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

{"title":"Synthesis and antiproliferative evaluation of novel chrysin selenocyanates","authors":"Zhiping Liu , Lijie Che , Yunlong Ban , Maixia Liu , Xiyan Tang , Yanmin Huang , Jianguo Cui , Chunfang Gan","doi":"10.1080/00397911.2024.2445860","DOIUrl":null,"url":null,"abstract":"<div><div>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 <strong>5c</strong> and <strong>5e</strong> exhibited the strongest inhibitory effects on SKOV-3 cells, with IC<sub>50</sub> 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.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 259-269"},"PeriodicalIF":1.8000,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124001498","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

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.

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

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.