N-benzoylated phenoxazines and phenothiazines: synthesis, antiproliferative activity, and inhibition of tubulin polymerization

H Prinz, B Chamasmani, K Vogel…

Index: Prinz, Helge; Chamasmani, Behfar; Vogel, Kirsten; Boehm, Konrad J.; Aicher, Babette; Gerlach, Matthias; Guenther, Eckhard G.; Amon, Peter; Ivanov, Igor; Mueller, Klaus Journal of Medicinal Chemistry, 2011 , vol. 54, # 12 p. 4247 - 4263

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Citation Number: 36

Abstract

A total of 53 N-benzoylated phenoxazines and phenothiazines, including their S-oxidized analogues, were synthesized and evaluated for antiproliferative activity, interaction with tubulin, and cell cycle effects. Potent inhibitors of multiple cancer cell lines emerged with the 10-(4-methoxybenzoyl)-10 H-phenoxazine-3-carbonitrile (33b, IC50 values in the range of 2– 15 nM) and the isovanillic analogue 33c. Seventeen compounds strongly inhibited tubulin ...