201664-47-3Relevant academic research and scientific papers
Design and synthesis of α-carboxy phosphononucleosides
Debarge, Sebastien,Balzarini, Jan,Maguire, Anita R.
, p. 105 - 126 (2011/04/17)
Rhodium catalyzed O-H insertion reactions employing α- diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5′-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.
Glycoconjugates, products of uridine derivatives phosphitylation and oxidation as glycosyltransferases potential inhibitors
Grec, Marta,Swierk, Piotr,Pastuch, Gabriela,Szeja, Wieslaw
, p. 652 - 663 (2011/06/19)
The title compounds, variously protected 5′-uridine derivatives connected with 1-thiosugar with thiophosphoesters fragment (17-22) were synthesized in sequence of reactions: phosphitylation - reaction of 5′-hydroxyl group of selectively protected nucleoside with a phosphitylating agent (N,N-diisopropyl chlorophosphoamidite), connection an phosphoroamidites with 2-bromoethanol or 3-bromopropanol and secondary oxidation with sulfur presence and finally condensation reaction of obtained products with 1-thiosugar. Received glycoconjugates (17-22) had a structure which mimic to structure of natural glycosyltransferases substrates.
Novel synthetic approach to multibenzoylated nucleosides
Zhu, Xue-Feng,Scott, A. Ian
, p. 1346 - 1354 (2008/09/19)
An improved and highly efficient synthetic approach to multibenzoylated nucleosides bearing free 5'-hydroxyl groups is described here. By employing t-butyldimethylsilyl (TBDMS) rather than the more commonly used dimethoxytrityl (DMTr) as a temporary 5'-OH
Transprotection of N-benzoylated nucleobase derivatives by dialkylaminomethylene group
Endova, Magdalena,Masojidkova, Milena,Rosenberg, Ivan
, p. 2151 - 2164 (2007/10/03)
The use of (chloromethylene)dialkylammonium chloride in selective transprotection of N-benzoylated nucleobase derivatives is reported along with the evaluation of the stability of various protecting groups widely used in nucleoside and/or nucleotide chemi
