- Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects
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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.
- 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.
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- Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells
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The design and first enantioselective synthesis of a series of chiral ferrocifens and ferrociphenols was realised by enantioselective palladium-catalysed intramolecular direct C?H bond activation followed by McMurry coupling. Biological evaluation revealed moderate anticancer activities on breast cancer cells and evidence of chiral discrimination between enantiomers. Treatment of the novel ferrocifens with Ag2O revealed that these systems are unable to form a neutral quinone methide, yet still demonstrate marked antiproliferative properties against both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 cell lines. This bioactivity arises from two mechanisms: Fenton-type chemistry and the anti-estrogenic activity associated with the tamoxifen-like structure.
- Cunningham, Laura,Wang, Yong,Nottingham, Chris,Pagsulingan, Jammah,Jaouen, Gérard,McGlinchey, Michael J.,Guiry, Patrick J.
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p. 2974 - 2981
(2020/07/04)
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- Palladium-catalyzed intramolecular asymmetric C-H functionalization/ cyclization reaction of metallocenes: An efficient approach toward the synthesis of planar chiral metallocene compounds
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A palladium-catalyzed asymmetric synthesis of planar chiral metallocene compounds is reported. The reaction stereoselectively functionalized one of the ortho C-H bonds of Cp rings by intramolecular cyclization to form indenone derivatives in high yields w
- Deng, Ruixian,Huang, Yunze,Ma, Xinna,Li, Gencheng,Zhu, Rui,Wang, Bin,Kang, Yan-Biao,Gu, Zhenhua
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supporting information
p. 4472 - 4475
(2014/04/17)
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