Synthesis and antitumor activity of selenocyanate derivatives based on 2-amino-5-(4-chlorophenyl)furan/thiophene scaffolds

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-08-18 DOI:10.1080/00397911.2025.2545850

Maixia Liu (Data curation Formal analysis Investigation Methodology) , Lijie Che (Methodology Resources Validation) , Xiyan Tang (Investigation Supervision) , Chunfang Gan (Data curation Software) , Yanmin Huang (Funding acquisition Project administration Writing – review & editing) , Zhiping Liu (Investigation Supervision Writing – original draft Writing – review & editing)

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引用次数: 0

Abstract

In this study, 2-amino-5-(4-chlorophenyl)furan/thiophene were synthesized via Paal-Knorr and Gewald cyclization strategies. A series of novel furan/thiophene selenocyanate derivatives were constructed by introducing selenocyanate groups with varying chain lengths through amide bonds. All compounds were structurally characterized using NMR and HR-MS analyses. MTT assay for antitumor activity revealed that several compounds exhibited superior efficacy compared to cisplatin. Notably, furan selenocyanate 5c showed significant inhibitory activity against HepG-2 cells (IC₅₀ = 8.64 ± 0.94 μM), while thiophene selenocyanate 11d demonstrated remarkable inhibition against HeLa and MCF-7 cells with IC₅₀ values of 6.39 and 6.77 μM, respectively. Structure-activity relationship (SAR) analysis indicated that the carbon chain length significantly influenced antitumor activity, with the C₈-chain thiophene selenocyanate derivative 11d exhibiting optimal selectivity for HeLa and MCF-7 cells. This study provides important references for development of novel selenium-containing antitumor drugs.

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基于2-氨基-5-（4-氯苯）呋喃/噻吩支架的硒氰酸酯衍生物的合成及其抗肿瘤活性

本研究通过Paal-Knorr和Gewald环化策略合成了2-氨基-5-（4-氯苯基）呋喃/噻吩。通过酰胺键引入不同长度的硒氰酸基团，构建了一系列新的呋喃/噻吩硒氰酸酯衍生物。所有化合物均通过NMR和HR-MS进行了结构表征。MTT抗肿瘤活性测定显示，几种化合物的抗肿瘤活性优于顺铂。其中，硒氰酸呋喃5c对HepG-2细胞的IC50值为8.64±0.94 μM，而硒氰酸噻吩11d对HeLa和MCF-7细胞的IC50值分别为6.39和6.77 μM。构效关系（SAR）分析表明，碳链长度显著影响其抗肿瘤活性，其中c8链硒氰酸噻吩衍生物11d对HeLa和MCF-7细胞具有最佳选择性。该研究为新型含硒抗肿瘤药物的开发提供了重要参考。

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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.