| 魏世贵,樊平平,杜永红,李进京.化学通报,2025,88(12):1333-1339. |
| 新型4-噻唑烷酮类化合物的合成及体外抗肿瘤活性评价 |
| Synthesis and in vitro anti-tumor activity evaluation of novel 4-thiazolidinone compounds |
| 投稿时间：2025-08-05 修订日期：2025-09-17 |
| DOI： |
| 中文关键词: 4-噻唑烷酮 苯并三唑 酰腙 合成 抗肿瘤活性 |
| 英文关键词:4-Thiazolidone, Benzotriazole, acylhydrazonpes, Synthesis, Antitumour activity |
| 基金项目:黑龙江省科技厅科技攻关项目(SZDYF202306)资助 |
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| 中文摘要: |
| 以2-(2-羟基-5-苯甲基)苯并三唑和2-溴乙酸乙酯为起始原料，经亲核取代反应合成酯类中间体5。中间体5再与水合肼反应生成酰肼中间体6。随后，中间体6与不同取代的异硫氰酸酯反应，得到相应的硫脲中间体7a~7g。最终，各种硫脲与2-溴乙酸乙酯经环合反应得到7个结构新颖的4-噻唑烷酮类化合物。目标化合物及中间体7a~7d均为首次报道的新化合物。所有目标化合物的结构经1H NMR、13C NMR及HRMS确证。采用MTT法评价7个目标化合物对人结肠癌细胞SW620、人非小细胞肺癌细胞A549、人宫颈癌细胞Hela和人乳腺癌细胞MCF-7的体外增殖抑制活性。初步的药理实验结果表明，新型4-噻唑烷酮类化合物中，化合物8b和8g对Hela细胞表现出显著的抑制效果，IC50值分别为10.8 μM和11.4 μM。对A549细胞表现出中等的抑制活性，IC50值分别为20.3 μM和16.1 μM。 |
| 英文摘要: |
| Using 2-(2H-benzo[d][1,2,3]triazol-2-yl)-4-methylphenol and ethyl 2-bromoacetate as starting materials, the ester intermediate 5 was synthesized via a nucleophilic substitution reaction. Intermediate 5 then underwent hydrazinolysis with hydrazine hydrate to form the hydrazide intermediate 6. Subsequently, intermediate 6 reacted with isothiocyanates bearing different substituents through a nucleophilic addition reaction, yielding the corresponding thiourea intermediates 7a~7g. Finally, various thioureas underwent intramolecular nucleophilic cyclization with ethyl 2-bromoacetate to construct the 4-thiazolidinone ring, affording seven novel 4-thiazolidinone compounds. Among them, the target compounds and intermediates 7a~7d are all novel compounds reported for the first time. The structures of all target compounds were confirmed by 1H NMR, 13C NMR and HRMS. MTT assay was used to evaluate the in vitro proliferation inhibitory activity of seven target compounds on human colon cancer cell SW620, human non-small cell lung cancer cell A549, human cervical cancer cell Hela and human breast cancer cell MCF-7. The preliminary pharmacological results showed that among the new 4-thiazolidinone compounds, compounds 8b and 8g showed significant inhibitory effects on Hela cells with IC50 values of 10.8 μM and 11.4 μM, respectively. It showed moderate inhibitory activity against A549 cells with IC50 values of 20.3 μM and 16.1 μM, respectively. |
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