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Short Paper | Regular issue | Vol 96, No. 7, 2018, pp.1289-1300
Published online, 25th June, 2018
DOI: 10.3987/COM-18-13931
Synthesis and DNA Cleavage Activity of Novel Spiro Pyrazol-3-ones Containing Isoxazoline Moiety

Eiichi Masumoto, Emi Shirouzu, Nobuhiro Kashige, Fumi Okabe-Nakahara, Fumio Miake, Kenji Yamagata, and Hiroshi Maruoka*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


An approach to the synthesis of novel spiro pyrazol-3-ones containing isoxazoline moiety is described. A plausible mechanism for the conversion is proposed. The spiro compounds were formed via potassium carbonate-assisted intramolecular cyclocondensation reaction of β-hydroxy ketoximes, which were prepared from pyrazol-3-ones containing β-hydroxy ketone moiety through an oximation. On the other hand, treatment of the β-hydroxy ketoximes with [hydroxy(tosyloxy)iodo]benzene (HTIB) caused an oxidative N–O coupling reaction to give the spiro pyrazol-3-ones containing isoxazoline N-oxide moiety. All the synthesized compounds were characterized by spectroscopic analysis and were tested for their DNA cleavage activity.