63593-02-2Relevant articles and documents
Synthesis of extended uridine phosphonates derived from an allosteric p2y2 receptor ligand
Song, Lijun,Risseeuw, Martijn D. P.,Karalic, Izet,Barrett, Matthew O.,Brown, Kyle A.,Harden, T. Kendall,Van Calenbergh, Serge
, p. 4313 - 4325 (2014)
In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 receptor ligands. A silyl-Hilbert- Johnson reaction of six quinazoline-2,4-(1H, 3H)-dione-like base moie
Synthesis and in vitro anticancer activity of penaresidin-related stereoisomeric analogues
Bodnár, Gergo,Kuchár, Juraj,Martinková, Miroslava,Nosálová, Natália,Pilátová, Martina Bago,Raschmanová, Jana ?paková
, (2021/08/23)
A straightforward route to penaresidin-based derivatives with an unsubstituted alkyl side chain was developed. To construct these stereoisomeric azetidene-derived alkaloids, [3,3]-sigmatropic rearrangements followed by late stage olefin cross metathesis and an intramolecular nucleophilic type substitution were involved as the key transformations. The protected D-ribofuranose was chosen as the sole chiral source. The ability of target molecules to inhibit cancer cells proliferation was evaluated on a panel of five malignant cell lines.
From Oxygen to Sulfur and Back: Difluoro -H-phosphinothioates as a Turning Point in the Preparation of Difluorinated Phosphinates: Application to the Synthesis of Modified Dinucleotides
Zhang, Jun,Lambert, Emilie,Xu, Ze-Feng,Brioche, Julien,Remy, Pauline,Piettre, Serge R.
, p. 5245 - 5260 (2019/05/10)
A simple, two-step procedure to convert α,α-difluorinated H-phosphinic acids into the corresponding H-phosphinothioates is described. The usefulness of these species is demonstrated by their transformation into difluorinated phosphinothioyl radicals and their addition onto alkenes. Additionally, sequential treatment of H-phosphinothioates by a strong base and a primary alkyl iodide constitutes an alternate route to the formation of the C-P bond. Both methods efficiently deliver difluorinated phosphinothioates. Similar reactions carried out with the fully oxygenated counterparts clearly indicate the superiority of the sulfur-based species and emphasize the crucial role played by sulfur in the construction of the second C-P bond. Oxidation easily transforms the thereby obtained phosphinothioates into the corresponding phosphinates. The whole strategy is applied to the stereoselective preparation of dinucleotide analogues featuring either a difluorophosphinothioyl or a difluorophosphinyl unit linking the two furanosyl rings.