3,5-Bis(arylidene)piperid-4-ones Containing 1,3,2-Oxazaphosphorinane Moieties: Synthesis and Antitumor Activity

作者：Shipov Anatolii E; Makarov Mikhail V^*; Petrovskii Pavel V; Rybalkina Ekaterina Yu; Nelyubina Yulia V; Odinets Irina L

来源：Heteroatom Chemistry, 2013, 24(3): 191-199.

DOI：10.1002/hc.21082

Two novel series of phosphorus-substituted 3,5-bis(arylidene)piperid-4-ones bearing 1,3,2-oxazaphosphorinane cycle either directly attached to the piperidone core through the PN bond (diamidophosphates 4) or connected with it via thiocarbamoyl linker (thioureas 5) were obtained by the phosphorylation of NH precursors with 2-oxo-1,3,2-oxazaphosphorinane chloride or the reaction of the former ones with the corresponding cyclic isothiocyanate. According to the results of cytotoxicity screening against human carcinoma cell lines (A549, CaOv3, KB), thioureas 5 were more active than the diamidophosphates 4 bearing the same arylidene rings, with compounds with electron-withdrawing side groups displaying IC50 in the micromolar range of 1.27 M.

• 出版日期2013