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Synthesis, Physical Properties, and Cytotoxicity of Nitroxyl–Aziridine Hybrid
Author(s) -
Kumamoto Takuya,
Suzuki Kazuya,
Kim Sangkook,
Hoshino Katsuyoshi,
Takahashi Masahiro,
Sato Hiromi,
Iwata Hiroki,
Ueno Koichi,
Fukuzumi Masahiro,
Ishikawa Tsutomu
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000076
Subject(s) - aziridine , chemistry , nitroxyl , yield (engineering) , ylide , electron paramagnetic resonance , cytotoxicity , stereochemistry , photochemistry , organic chemistry , ring (chemistry) , nuclear magnetic resonance , in vitro , biochemistry , materials science , metallurgy , physics
Nitroxyl–aziridine hybrid, a candidate for a magnetic resonance imaging (MRI) probe and an anticancer drug, was synthesized by aziridine formation reaction of nitroxyl‐introduced aldehyde and guanidinium ylide in good diastereoselectivity. The relative configuration at aziridine C(2)C(3) bond of the major diastereoisomer was determined to be cis by X‐ray crystallographic analysis. Application of chiral guanidinium ylide resulted in the formation of the corresponding optically active aziridine in 84% ee. Reversible one‐electron redox potential and quantitative spin yield of the hybrid were observed in cyclic voltammogram and electron spin resonance, respectively. However, cytotoxicity of the hybrid against cancer cell lines used was not observed.