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Short Paper | Special issue | Vol 99, No. 1, 2019, pp.669-679
Published online, 19th October, 2018
DOI: 10.3987/COM-18-S(F)34
Synthesis and DNA Cleavage Activity of Novel Spiro[cyclobutathiazole-4,4’-pyrazole] Derivatives

Eiichi Masumoto, Hayate Nagabuchi, 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


A facile and efficient synthesis of novel spiro pyrazole derivatives containing cyclobutathiazole moiety is described. The key substrate pyrazole-thiazolidine derivative as the building block for bis-heterocycles was formed via a Knoevenagel-type condensation of thiazolidinedione with pyrazol-3-one. Thermal treatment of the pyrazole-thiazolidine derivative with orthoesters in refluxing toluene caused an C-attack nucleophilic substitution, followed by an intramolecular cyclization/elimination sequence, giving the corresponding spiro[cyclobutathiazole-4,4’-pyrazole] derivatives. All the synthesized compounds were characterized by spectroscopic analysis and were tested for their DNA cleavage activity in vitro.