Synthesis, Electrochemistry and Antitumor Activity of 1’H, 3’H(Me)-spiro-[(aza)benzimidazoline-2’, 3-(1,2-diferrocenylcyclopropenes)], 2-(1,2-Diferrocenylvinyl)benz- and Azabenzimidazoles

• 作者: Elena I. Klimova Elena Martínez-Klimova Jessica J. Sánchez García Juan C. García Ramos Luis Ortiz-Frade Marcos Flores-Alamo Teresa Ramírez Apan
• 来源期刊: 合成理论与应用(英文)
• 学科: 化学
• 关键词: Diferrocenyl(methylthio)cyclopropenylium 2-(1 2-Diferrocenylvinyl)(aza)benzimidazoles 1’H 3’H(Me)-spiro-[(aza)benzimidazoline-2’ 3-(1 2-diferrocenylcyclopropenes)] ELECTROCHEMISTRY Antitumor Activity
• 年，卷（期）: 2014,（4）
• 页码范围: 44-56
• 页数: 13页
• 分类号: O6

摘要

A new method of synthesis of 2-(1,2-diferrocenylvinyl)benz- and azabenzimidazoles (3a-f), (4a-f) and 1’H,3’H(Me)-spiro-[(aza)benzimidazoline-2’,3-(1,2-diferrocenylcyclopropenes)] (5a-f) via reactions of diferrocenyl(methylsulfanyl)cyclopropenylium iodide (1) with aromatic o-diamines (2a-f) in the presence of Et3N (80°C - 82°C) is described. The structures of the resultant compounds are established using IR, 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The structure of one compound, cis-2-(1,2-diferrocenylvinyl)-1-methylbenzimidazole (3b), is confirmed by X-ray diffraction analysis. The electrochemical properties of compounds 3a, 3b, 3d and 5f are investigated using cyclic square wave voltammetry. Two electrochemical processes (I-II), attributed to oxidation of the ferrocene moieties, and the values of E0’(I), E0’(II), DE0’(II-I) and comporportionation constant Kcom are reported. The bioactivities of seven compounds 3a, 3c-f, 5d, 5f are evaluated. Compound 5f is the most active compound with a modest cytotoxic activity against six human cancer cell lines: U-251 (glioma), PC-3 (prostate cancer), K-562 (leukemia), HCT-15 (colon cancer), MCF-7 (breast cancer) and SKLU-1 (lung cancer).