Zhang Hong, Wang Jianyuan, Li Cheng, Zhao Di, Liang Tianyu, Li Yang
College of Chemistry and Materials Engineering, Bohai University No. 19, Keji Street Jinzhou P. R. China
Department of Chemical Engineering, Fushun Teacher's College No. 103, Wenhua Street Fushun P. R. China.
RSC Adv. 2024 Aug 23;14(37):26820-26828. doi: 10.1039/d4ra04588b. eCollection 2024 Aug 22.
In this work, a green, efficient and catalyst-free synthesis of a series of structurally novel ()-diethyl 2-styrylquinoline-3,4-dicarboxylates a direct olefination reaction between diethyl 2-methylquinoline-3,4-dicarboxylate and various aromatic aldehydes was successfully accomplished by employing eco-friendly 1,3-dimethylurea/l-(+)-tartaric acid (DMU/LTA) as an inexpensive, non-toxic and reusable reaction medium. This methodology has the attractive advantages of mild reaction conditions, simple experimental operation, and the absence of any dangerous catalysts or unsafe volatile organic solvents, with satisfactory to good yields. Subsequently, a primary evaluation for their anti-proliferative activity against human cancer cell lines A549, HT29 and T24 revealed that the compound with the 3,4,5-trimethoxystyryl moiety exhibited potent anti-tumor activity with IC values of 2.38, 4.52 and 9.86 μmol L, respectively, thereby being equipotent or even better than the reference cisplatin.
在本工作中，通过使用环保的1,3 - 二甲基脲/ L-(+)-酒石酸（DMU/LTA）作为廉价、无毒且可重复使用的反应介质，成功实现了一系列结构新颖的（）-2-苯乙烯基喹啉-3,4-二羧酸二乙酯的绿色、高效且无催化剂合成，即2-甲基喹啉-3,4-二羧酸二乙酯与各种芳香醛之间的直接烯化反应。该方法具有反应条件温和、实验操作简单、无需任何危险催化剂或不安全挥发性有机溶剂的诱人优点，产率令人满意或良好。随后，对它们针对人癌细胞系A549、HT29和T24的抗增殖活性进行的初步评估表明，具有3,4,5-三甲氧基苯乙烯基部分的化合物表现出强效抗肿瘤活性，IC值分别为2.38、4.52和9.86 μmol/L，从而与参考顺铂相当甚至更好。
