Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates

Novel bis-heterocyclic bisphosphonates/phosphonamidates were synthesized utilizing the Pudovick reaction. The employment of Nb2O5 as catalyst was found to increase the yields and purity of the bisbenzoxazaphosphine derivatives (13a–h). Their anticancer activity studies in vitro, on three human tumor cell lines NCI-H460 (lung large cell), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioblastoma), showed that bis-[3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2λ5-benzo[e][1,3,2]oxazaphosphinin-2-yl]arylmethanes (13a–h) and [(4-chlorophenyl)-(hydroxyamidophosphinoyl)-methyl]phosphonic acid (14) exhibited significant anticancer activity.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide