The outstanding evidence of phthalimide pharmacophore in securing enhanced biological activities had encouraged further research and development into phthalimide-based derivatives as potential new drugs. In this study, phthalimide core was hybridized with aldehydes giving integrated imines displaying different types of functionalities and at alternating positions. The resulting compounds, therefore, provide an innovative window to explore possible differential biological effects as antioxidants and anticancer agents. A total of sixteen compounds were synthesized, and each was verified by FT-IR, H NMR, C NMR, and MS characterization. Herein, a facile single-step synthesis method was employed substituting the conventional two-step chemical production routes. Among the sixteen tested compounds, the H7 compound with hydroxyl phenolic group has shown an eminent antioxidant activity with a 19.52% decrease to the IC50 value compared to that of the control standard BHT antioxidant. On the other hand, the halogenated H6 Schiff base structure was successful in securing effective cancer inhibition to both colon and breast cancer cell lines, while maintaining selective action toward normal tissues. Results have collectively indicated the importance and impactful effects of functional groups position and types within similar basic structures, in directing different biological outcomes.

中文翻译：

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作为潜在抗癌剂的邻苯二甲酰亚胺亚胺衍生物的合成

邻苯二甲酰亚胺药效团在确保增强生物活性方面的突出证据鼓励进一步研究和开发基于邻苯二甲酰亚胺的衍生物作为潜在的新药。在这项研究中，邻苯二甲酰亚胺核与醛杂化，产生显示不同类型功能和交替位置的集成亚胺。因此，由此产生的化合物为探索作为抗氧化剂和抗癌剂的可能不同生物效应提供了一个创新的窗口。共合成了 16 种化合物，每种化合物均通过 FT-IR、H NMR、C NMR 和 MS 表征验证。在此，采用简便的单步合成方法替代了传统的两步化学生产路线。在 16 种测试化合物中，与对照标准 BHT 抗氧化剂相比，具有羟基酚基团的 H7 化合物显示出卓越的抗氧化活性，IC50 值降低了 19.52%。另一方面，卤化 H6 席夫碱结构成功地确保了对结肠癌细胞系和乳腺癌细胞系的有效癌症抑制，同时保持了对正常组织的选择性作用。结果共同表明了类似基本结构中功能组位置和类型在指导不同生物学结果方面的重要性和影响。卤化 H6 席夫碱结构成功地确保对结肠癌细胞系和乳腺癌细胞系的有效癌症抑制，同时保持对正常组织的选择性作用。结果共同表明了类似基本结构中功能组位置和类型在指导不同生物学结果方面的重要性和影响。卤化 H6 席夫碱结构成功地确保对结肠癌细胞系和乳腺癌细胞系的有效癌症抑制，同时保持对正常组织的选择性作用。结果共同表明了类似基本结构中功能组位置和类型在指导不同生物学结果方面的重要性和影响。