4348-69-0Relevant articles and documents
MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF
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Page/Page column 115-116, (2021/02/19)
The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.
An economical synthesis of D- and L-pyrimidine arabinoand ribonucleosides
Lazrek, Hassan B.,Ouzebla, Driss,Faraj, Abdesslem
experimental part, p. 227 - 234 (2012/04/18)
The one-step synthesis of several β-D/L-arabino- and ribonucleosides was performed in good yields under reflux or microwave-assisted fusion method. A comparison of the two methods showed that better yields were obtained using the reflux conditions. Copyright Taylor and Francis Group, LLC.
Enantioselective synthesis and biological evaluation of 5-o-carboranyl pyrimidine nucleosides
Mourier, Nicolas S.,Eleuteri, Alessandra,Hurwitz, Selwyn J.,Tharnish, Phillip M.,Schinazi, Raymond F.
, p. 2759 - 2766 (2007/10/03)
Base-modified carborane-containing nucleosides such as 5-o-carboranyl-2'-deoxyuridine (CDU) when combined with neutrons have potential for the treatment of certain malignancies. Lack of toxicity in various cells, high accumulation in cancer cells and intracellular phosphorylation are desirable characteristics for modified nucleosides used in boron neutron capture therapy (BNCT) for brain tumors and other malignancies. The aim of this work was to synthesize the two β-enantiomers of several 5-o-carboranyl-containing nucleosides. These derivatives may possess favorable properties such as high lipophilicity, high transportability, the ability to be phosphorylated, and resistance to catabolism. β-Isomers of 2',3'-dihydroxynucleosides and analogues containing a heteroatom in the sugar moiety were also synthesized. Carboranyl pyrimidine nucleosides were prepared either from the parent β-D-nucleoside, β-L-nucleoside, or by a coupling reaction. The dioxolane derivative 7Scheme 1Reagents and conditions: (a) 1,1,1,3,3,3-hexamethydisilazane, ammonium sulfate, reflux, 6 h; (b) tin(IV) chloride, CH2Cl2, 0°C, 2h; (c) tetrabutylammonium fluoride, 1 M sol in THF, 0°C, 3h. was prepared by a coupling reaction between protected 5-o-carboranyluracil (8, CU) and the corresponding protected heterocycle. Specific catalysts were used during the N-glycosylation process to favor the formation of the β-isomer. Biological evaluation of these new chiral 5-o-carboranyl pyrimidine derivatives indicated that most of these compounds have low toxicity in a variety of normal and malignant cells and achieved high cellular levels in a lymphoblastoid cell line. Increasing the number of hydroxyl groups on the sugar moiety decreased the cellular accumulation and serum binding to different extents. Five compounds were identified for further biological evaluation as potential agents for BNCT. Copyright (C) 1999 Elsevier Science Ltd.