33876-85-6Relevant academic research and scientific papers
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
New efficient synthesis of 1-hydroxymethylene-1,1-bisphosphonate monomethyl esters
Migianu, Evelyne,Guénin, Erwann,Lecouvey, Marc
, p. 425 - 428 (2007/10/03)
A new efficient procedure for the synthesis of 1-hydroxymethylene-1,1- bisphosphonate monomethyl esters in three steps from acid chlorides is reported here. Georg Thieme Verlag Stuttgart.
THE REACTION OF BENZOYLPHOSPHONIC ACID WITH THIONYL CHLORIDE. THE FORMATION OF BENZOYLPHOSPHONIC DICHLORIDE AND P,P'-DIBENZOYLPYROPHOSPHONIC DICHLORIDE
Bentolila, Alfonso,Katzhendler, Jehoshua,Breuer, Eli
, p. 109 - 112 (2007/10/02)
The reaction of benzoylphosphonic acid (3) with thionyl chloride leads to the formation of benzoylphosphonic dichloride (5) and P,P'-dibenzoylpyrophosphonic dichloride (6).These products were identified by (31)P nmr spectra and through their products of a
