Novel diiron vinyliminium complexes, [Fe₂Cp₂(CO)(μ-CO){μ-η¹:η³-C(R³)CHCNMe(R²)}]CF₃SO₃ (2a–f; R² = 4-C₆H₄OMe, Cy or Me; R³ = Cy, CH₂Cy or 4-C₆H₄OMe; Cy = cyclohexyl, Cp = η⁵-C₅H₅), were synthesized by alkyne insertion reaction from the corresponding diiron aminocarbyne precursors, and isolated in 53–98% yields. The reactions of selected vinyliminium complexes with N₂CHCO₂Et and MeONa, followed by N-methylation, afforded the new hydrazone-vinyliminium [Fe₂Cp₂(CO)(μ-CO){μ-η¹:η³-C(R³)C(NMeNCHCO₂Et)CN(R¹)(R²)}]X (4a–c; R¹ = Me or CH₂Ph; R² = Cy, CH₂Ph or Me; R³ = 4-C₆H₄OMe or Ph; X = NO₃ or CF₃SO₃), in 53–67% yields. Compounds 2a–f and 4a–c were fully characterized by IR and multinuclear NMR spectroscopy, and the structures of 2a–c were ascertained by single crystal X-ray diffraction. Moreover, D₂O solubility, Log P_ow coefficients and the fraction of each complex preserved in aqueous media after 72 hours at 37 °C were determined by ¹H NMR and UV-Vis methods. The antiproliferative activity of 2a–f and 4a–c was measured on the mouse colon CT26 and human glioblastoma U87 cancer cell lines, and on the retinal pigment epithelial RPE-1 non-cancerous cell line. Complexes 2a,d,e, which all bear R³ = Cy, stand out for their performance and their selectivity towards cancer cells. To give insight into the mechanism of action, the effect of 2a, 2d, 2e, 2f, 4b and 4c on the mitochondrial respiration was evaluated in CT26 cells (Seahorse Mito stress test), revealing a correlation between the effectiveness of the complexes and their influence on the mitochondrial metabolism.

中文翻译：

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环己基取代基对二铁乙烯基亚胺配合物体外抗癌活性的有益影响

新型二铁乙烯基亚胺配合物，[Fe ₂ Cp ₂ (CO)(μ-CO){μ-η ¹ :η ³ -C(R ³ ) CHC NMe(R ² )}]CF ₃ SO ₃ ( 2a–f ; R ² = 4-C ₆ H ₄ OMe、Cy 或 Me；R ³ = Cy、CH ₂ Cy 或 4-C ₆ H ₄ OMe；Cy = 环己基，Cp = η ⁵ -C ₅ H ₅), 由相应的二铁氨基卡炔前体通过炔烃插入反应合成，并以 53-98% 的收率分离。_{选定的乙烯基亚胺络合物与 N 2} CHCO ₂ Et 和 MeONa反应，然后进行N-甲基化，得到新的腙-乙烯基亚胺 [Fe ₂ Cp ₂ (CO)(μ-CO){μ-η ¹ :η ³ -C (R ³ )C(NMeN CHCO ₂ Et)CN(R ¹ )(R ² )}]X ( 4a–c ; R ¹ = Me 或 CH ₂ Ph; R ² = Cy, CH ₂ Ph 或 Me; R ³ = 4-C₆ H ₄ OMe或Ph；X = NO ₃或 CF ₃ SO ₃ )，产率为 53–67%。化合物2a-f和4a-c已通过红外和多核 NMR 光谱充分表征， 2a-c的结构通过单晶 X 射线衍射确定。^{此外，通过1} H NMR 和 UV-Vis 方法测定D ₂ O 溶解度、Log  Pow系数和在 37 °C 下 72_{小时后保存在水性介质中的每种复合物的分数。}2a-f和4a-c的抗增殖活性在小鼠结肠 CT26 和人胶质母细胞瘤 U87 癌细胞系以及视网膜色素上皮 RPE-1 非癌细胞系上测量。复合物2a、d、e均具有 R ³ = Cy，因其性能和对癌细胞的选择性而引人注目。为了深入了解作用机制，在 CT26 细胞（Seahorse Mito 压力测试）中评估了2a、2d、2e、2f、4b和4c对线粒体呼吸的影响，揭示了复合物的有效性与其作用之间的相关性对线粒体代谢的影响。