N-phosphorylated 3,5-bis(arylidene)4-piperidones: Synthesis, X-ray structure, and evaluation of antitumor activity

Abstract

In a search for cytotoxic fluorescent materials, a series of N-phosphorylated compounds 2a-c were prepared by phosphorylation of 3,5-bis(4-N,N-dimethylbenzylidene)-4-piperidone 1. According to X-ray investigations, molecule 2a is E,E-isomer with axial position of the P(O)(OCH2CF3)2 substituent. Fluorescence of compounds 2a-c was found to be similar to fluorescence of nonphosphorylated compound 1. The cytotoxicity of the compounds 2a-c was estimated on several human tumor cell lines (H9, K562, and MCF7). © 2005 Wiley Periodicals, Inc.