26929-65-7Relevant articles and documents
Synthesis of 2′-aminouridine derivatives as an organocatalyst for Diels-Alder reaction?
Wakamatsu, Hideaki,Itoh, Moeko,Natori, Yoshihiro,Yoshimura, Yuichi
, p. 365 - 383 (2020)
To develop a novel asymmetric organocatalyst based on a ribonucleoside skeleton, we designed and synthesized 2′-aminouridine derivatives. The synthesized 2′-aminouridines having bulky substituents at both base and sugar moieties could catalyze the Diels-Alder reaction between cinnamaldehyde and cyclopentadiene. However, the optical purities of the resulting products were unexpectedly low.
Site of azido substitution in the sugar moiety of azidopyrimidine nucleosides influences the reactivity of aminyl radicals formed by dissociative electron attachment
Mudgal, Mukesh,Dang, Thao P.,Sobczak, Adam J.,Lumpuy, Daniel A.,Dutta, Priya,Ward, Samuel,Ward, Katherine,Alahmadi, Moaadh,Kumar, Anil,Sevilla, Michael D.,Wnuk, Stanislaw F.,Adhikary, Amitava
, p. 11357 - 11370 (2020)
In this work, electron-induced site-specific formation of neutral π-type aminyl radicals (RNH·) and their reactions with pyrimidine nucleoside analogs azidolabeled at various positions in the sugar moiety, e.g., at 2′-, 3′-, 4′-, and 5′- sites along with a model compound 3-azido-1-propanol (3AZPrOH), were investigated. Electron paramagnetic resonance (EPR) studies confirmed the site and mechanism of RNH· formation via dissociative electron attachment-mediated loss of N2 and subsequent facile protonation from the solvent employing the 15N-labeled azido group, deuterations at specific sites in the sugar and base, and changing the solvent from H2O to D2O. Reactions of RNH· were investigated employing EPR by warming these samples from 77 K to ca. 170 K. RNH· at a primary carbon site (5′-azido-2′,5′-dideoxyuridine, 3AZPrOH) facilely converted to a σ-type iminyl radical (R=N·) via a bimolecular H-atom abstraction forming an α-azidoalkyl radical. RNH· when at a secondary carbon site (e.g., 2′-azido-2′-deoxyuridine) underwent bimolecular electrophilic addition to the C5=C6 double bond of a proximate pyrimidine base. Finally, RNH· at tertiary alkyl carbon (4′-azidocytidine) underwent little reaction. These results show the influence of the stereochemical and electronic environment on RNH· reactivity and allow the selection of those azidonucleosides that would be most effective in augmenting cellular radiation damage.
An Improved Synthesis of 2'-Azido-2'-Deoxyuridine
Kirschenheuter, Gary P.,Zhai, Yansheng,Pieken, Wolfgang A.
, p. 8517 - 8520 (1994)
A high yield process for the conversion of 2,2'-cyclouridine to 2'-azido-2'-deoxyuridine was developed.The procedure utilizes a lithium azide:TMEDA complex generated in situ from the reaction of lithium fluoride and azidotrimethylsilane in DMF with TMEDA added as a co-solvent.
RELEASABLE CONJUGATES
-
Page/Page column 173; 174, (2018/09/28)
The present application provides compounds of Formula (B), or pharmaceutically acceptable salts thereof, wherein D is a residue of a biologically active drug, which underdo hydrolysis under physiological conditions to release the biologically active drug and which are useful in the treatment of disorders that could be beneficially treated with the drug.
Cu(I)-catalyzed efficient synthesis of 2'-triazolo-nucleoside conjugates
Mathur,Rana,Olsen,Parmar,Prasad
, p. 701 - 710 (2015/05/13)
A small library of thirty-two 2'-triazolyl uridine and 2'-triazolyl-5-methyluridine has been synthesized by Cu(I)-catalyzed condensation of 2'-azido-2'-deoxyuridine and 2'-azido-2'-deoxy-5-methyluridine with different alkynes and aryl propargyl ethers in almost quantitative yields. Triazolo-nucleoside conjugates, which can be evaluated for different biological activity for suitable drug development, were unambiguously identified on the basis of 1H NMR, 13C NMR, IR, and HRMS data analysis. These compounds have been synthesized for the first time and have not been reported in the literature earlier.
