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. Heteroatom Chem 16:497–502, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20147