55123-32-5Relevant academic research and scientific papers
Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities
Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.
, p. 2770 - 2779 (2014/05/06)
Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright
A selective synthesis of protected a-dglucofuranurono- 6,3-lactone chloride using bismuth (iii) chloride as catalyst
Ionescu, Catalina,Awwad, Azzam,Barragan, Veronique,Montero, Jean-Louis
experimental part, p. 193 - 197 (2011/07/30)
A new and specific route for the synthesis of peracetylated-α- glucofuranurono-6,3-lactone chloride has been described using bismuth (III) chloride and methyltrichlorosilane as chlorinating agents.
