33876-85-6Relevant articles and documents
One-pot synthesis of phosphinylphosphonate derivatives and their anti-tumor evaluations
Deschamp, Julia,Dussart-Gautheret, Jade,Lecouvey, Marc,Legigan, Thibaut,Migianu-Griffoni, Evelyne,Monteil, Maelle
, (2021/12/24)
This paper reports on the synthesis of new hydroxymethylene-(phosphinyl)phosphonates (HMPPs). A methodology has been developed to propose an optimized one-pot procedure without any intermediate purifications. Various aliphatic and (hetero)aromatic HMPPs were synthesized in good to excellent yields (53–98%) and the influence of electron withdrawing/donating group substitution on aromatic substrates was studied. In addition, the one-pot synthesis of HMPP was monitored by31P NMR spectroscopy, allowing effective control of the end of the reaction and identification of all phosphorylated intermediate species, which enabled us to propose a reaction mechanism. Optimized experimental conditions were applied to the preparation of biological relevant aminoalkyl-HMPPs. A preliminary study of the complexation to hydroxyapatite (bone matrix) was carried out in order to verify its lower affinity towards bone compared to bisphosphonate molecules. Moreover, in vitro anti-tumor activity study revealed encouraging antiproliferative activities on three human cancer cell lines (breast, pancreas and lung).
Novel approach to nucleoside-5′-(1-hydroxymethylene-1, 1-bisphosphonates): Synthesis of new AZT analogues
Migianu, Evelyne,Monteil, Maelle,Even, Pascale,Lecouvey, Marc
, p. 121 - 133 (2007/10/03)
An efficient synthetic method of nucleoside-5′-(1-hydroxymethylene-1, 1-bisphosphonates) is reported here. The procedure was optimized with 3′-protected thymidine and then applied to synthesis of new AZT analogues. Copyright
