Synthesis, structure and redox potentials of biologically active ferrocenylalkyl azoles |
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| Authors: | Lubov’ V Snegur Alexander A Simenel Elena A Morozova Svetlana M Peregudova Valery N Babin Natalia V Bluchterova |
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| Institution: | a A.N. Nesmeyanov Institute of OrganoElement Compounds, Russian Academy of Sciences, 28 Vavilov St., 119991 Moscow, Russian Federation
b N.M. Emanuel Institute of Biochemical Physics, 4 Kosigina St., 119991 Moscow, Russian Federation |
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| Abstract: | The syntheses, structures, electrochemical properties of the series of ferrocenylalkyl azoles, FcAlkAz, as well as the antitumor activity of ferrocenylmethyl benzimidazole (8) have been studied. Above mentioned compounds were investigated by the method of cyclic voltametry. All of them exhibited a reversible one-electron oxidation-reduction wave owing to the ferrocene-ferrocenium redox couple with a positive shift (0.50-0.65 V) compared with that of ferrocene (0.42 V). The X-ray determination of molecular structures of 1-(ferrocenylmethyl)imidazole (4), 1-(ferrocenylbenzyl)imidazole (7) and 1-(ferrocenylmethyl)bezimidazole (8) was carried out. Compound 4 with imidazolyl substituent was found to be present in N-protonated form. Antitumor activity of 1-(ferrocenylmethyl)benzimidazole (8) against some solid tumor models such as adenocarcinoma 755 (Ca755), melanoma B16 (B16) and Lewis lung carcinoma was studied. The antitumor activity of compound 8 was compared with cisplatin effectiveness against some experimental tumor systems. |
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| Keywords: | Ferrocenylalkyl azoles Ferrocene derivatives Electrochemistry (cyclic voltametry) X-ray crystal structure Antitumor activity Experimental tumor systems |
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