Journal of Organometallic Chemistry p. 10 - 20 (2018)
Update date:2022-08-24
Topics:
Snegur, Lubov V.
Lyapunova, Maria V.
Verina, Daria D.
Kachala, Vadim V.
Korlyukov, Alexander A.
Ilyin, Mikhail M.
Davankov, Vadim A.
Ostrovskaya, Larissa A.
Bluchterova, Natalia V.
Fomina, Margarita M.
Malkov, Victor S.
Nevskaya, Kseniya V.
Pershina, Alexandra G.
Simenel, Alexander A.
Ferrocenylalkyl 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, 5c in vitro, and in experiments in vivo antitumor effects of 1-N-ferrocenylethyl-4-nitroimidazole (4b) against murine solid tumor system Ca755 carcinoma were evaluated.
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Doi:10.1039/c5ra17028a
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