Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates

A series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates was synthesized and their cytotoxic activities were tested against various human tumor cell lines. Some compounds (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. Especially, compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells with IC50 7.1 and 11.4 μM, respectively. Their inhibitory activities against KB and CNE2 cells were even higher than that of fluorouracil.

Graphical abstractA series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates was synthesized and the compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells, respectively.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates was synthesized. ► Some of them (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. ► Compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells, respectively, higher than that of fluorouracil.