Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects

Publication date: 15 September 2018Source: Journal of Organometallic Chemistry, Volume 871Author(s): Lubov V. Snegur, Maria V. Lyapunova, Daria D. Verina, Vadim V. Kachala, Alexander A. Korlyukov, Mikhail M. Ilyin, Vadim A. Davankov, Larissa A. Ostrovskaya, Natalia V. Bluchterova, Margarita M. Fomina, Victor S. Malkov, Kseniya V. Nevskaya, Alexandra G. Pershina, Alexander A. SimenelAbstractFerrocenylalkyl nitro-imidazoles (4a-h, 5a-h) were prepared via the regiospecific reaction of the α-(hydroxy)alkyl ferrocenes, FcCHR (OH) (1a–h; Fc = ferrocenyl; R = H, Me, Et, Pr, i-Pr, Ph, ortho-Cl-Ph, ortho-I-Ph), with nitro-imidazoles in aqueous organic medium (H2O-CH2Cl2) at room temperature in the presence of HBF4, within several minutes in good yields. X-ray structural data for racemic (R,S)-1-N-(benzyl ferrocenyl)-2-methyl-4-nitroimidazole (5f) were determined. The resulting enantiomers were resolved into enantiomers by analytical HPLC on modified amylose or cellulose chiral stationary phases. The viabilities of 4b, 4d, 5b, 5cin vitro, and in experiments in vivo antitumor effects of 1-N-ferrocenylethyl-4-nitroimidazole (4b) against murine solid tumor system Ca755 carcinoma were evaluated.Graphical abstract
Source: Journal of Organometallic Chemistry - Category: Chemistry Source Type: research