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

Jessica J. Sánchez García¹, Luis Ortiz-Frade², Elena Martínez-Klimova³, Juan C. García Ramos¹, Marcos Flores-Alamo¹, Teresa Ramírez Apan⁴, Elena I. Klimova^1*

¹Faculty of Chemistry, University National Autonomous of México, México City, México.
²Centre of Investigation and Development Technology in Electrochemistry S.C., Queretaro, México.
³Departament of Bioengineering, South Kensington, Imperial College London, London, UK.
⁴Institute of Chemistry, University National Autonomous of México, México City, México.

DOI: 10.4236/ojsta.2014.34007                

Abstract

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 E^0’(I), E^0’(II), DE^0’(II-I) and comporportionation constant K_com 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).

Keywords

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

Conflicts of Interest

The authors declare no conflicts of interest.

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