Journal ArticleDOI
Synthesis and hydrolytic stability of the α and β anomers of 4′-thio-2′-deoxyuridine and their 5-substituted analogs. Competition between the acid-catalysed depyrimidination and isomerisation to a 5-thiopyranoside nucleoside
Graham P. Otter,Mohamed I. Elzagheid,Garry D. Jones,Alasdair C. MacCulloch,Richard T. Walker,Mikko Oivanen,Karel D. Klika +6 more
Reads0
Chats0
TLDR
The α and β anomers of 4′-thio-2′-deoxyuridine were readily synthesised as an anomeric mixture using adapted methodology and separated chromatographically as their 3′,5′-di-O-benzyl derivatives as discussed by the authors.Abstract:
The α and β anomers of 4′-thio-2′-deoxyuridine were readily synthesised as an anomeric mixture using adapted methodology and separated chromatographically as their 3′,5′-di-O-benzyl-N
3-benzoyl derivatives. The 5-fluoro analogs were prepared in a similar manner, but the anomers could be separated simply as their 3′,5′-di-O-benzyl derivatives. The kinetics of acid-catalysed hydrolysis for the four compounds and their 5-alkylated analogs are reported. Under these conditions, cleavage of the N-glycosidic bond competes with the reversible isomerisation between the furano (4′-thio) and pyrano (5′-thio) ring systems. This was confirmed by isolation and NMR characterisation of the α and β pyranose intermediates of the parent compounds.read more
Citations
More filters
Journal Article
Evaluation of 4′-[Methyl-14C]Thiothymidine for In Vivo DNA Synthesis Imaging
TL;DR: The labeling procedure is rapid and suitable for 11C labeling, and positron-labeled 4'-thiothymidine should be useful for imaging DNA synthesis by PET.
Journal ArticleDOI
Synthesis and Structural Elucidation of 2′‐Deoxy‐4′‐thio‐L‐threo‐pentofuranosylpyrimidine and ‐purine Nucleosides
TL;DR: In this article, a glycosyl donor for the synthesis of 4′-thio-L-threo-pentofuranosyluracil derivatives was used for X-ray structural analyses.
Journal ArticleDOI
An improved large scale synthesis of 1,4-anhydro-4-thio-d-ribitol
TL;DR: An improved large scale synthesis of 1,4-anhydro-4-thio- d -ribitol (4 ) from d-ribose has been accomplished by combining the O -allyl and O - p -methoxybenzyl protecting groups as discussed by the authors.
Journal ArticleDOI
Recent developments in the synthesis, chemical modifications and biological applications of sulfur modified nucleosides, nucleotides and oligonucleotides
TL;DR: This work focuses on the synthesis and modification of Thiobases Containing Nucleosides and Nucleotides using Sulfur in Glycosidation Methods and its application in the HETEROCYCLIC BASE.
Journal ArticleDOI
Alkyl-fluorinated thymidine derivatives for imaging cell proliferation II. Synthesis and evaluation of N3-(2-[18F]fluoroethyl)-thymidine.
TL;DR: It is concluded that N(3)-(2-[(18)F]fluoroethyl)-thymidine ([(14)C]NFT202 is not a suitable PET ligand for imaging tumor cell proliferation.
References
More filters
Journal ArticleDOI
Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides.
TL;DR: All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines and 4'-Thiothymidine was also active against herpes simplex 1 and human cytomegalovirus in cell culture.
Journal ArticleDOI
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
TL;DR: Three 2'-deoxy nucleoside analogues have been synthesized that are toxic, not toxic nor has detectable biological activity, and the third is not toxic and has significant activity against some herpesviruses.
Journal ArticleDOI
Synthesis and anti-herpes virus activity of 2'-deoxy-4'-thiopyrimidine nucleosides.
S. G. Rahim,N. Trivedi,M. V. Bogunovic‐Batchelor,G. W. Hardy,G. Mills,J. W. T. Selway,W. Snowden,E. Littler,Paul L. Coe,I. Basnak,R. F. Whale,Richard T. Walker +11 more
TL;DR: A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents and the compound with the broadest spectrum of activity was 2'- deoxy-5-ethyl- 4'-thiouridine which showed significant activity against HSV-1, HSV2, and VZV.
Journal ArticleDOI
An improved synthesis of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-d-erythro-pentofuranoside, an intermediate in the synthesis of 4′-thionucleosides
TL;DR: The first dithioacetal derivatives of 2-deoxy-d - erythro -pentose were prepared in exploratory routes to the described thio sugar or as intermediates as mentioned in this paper.
Related Papers (5)
An improved synthesis of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-d-erythro-pentofuranoside, an intermediate in the synthesis of 4′-thionucleosides
Synthesis of 5-substituted ether derivatives of 5-hydroxymethyldeoxyuridine and their α-anomers
G. L. Bubbar,V. S. Gupta +1 more