The Synthesis and Biological Activity of 1-(2-Deoxy-4-Thio-α;-L-Threo-Pentofuranosyl)Thymine
- 1 September 1993
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 12 (8) , 841-846
- https://doi.org/10.1080/07328319308018554
Abstract
The procedure of Huang and Hui (Nucleosides & Nucleotide 1993, 12, 139-147) was found to give benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-L-threo-pentofuranoside (6) rather than the claimed D-erythro isomer. This sugar was converted to an anomeric mixture of the thymine nucleosides. The mixture was separated and the α-anomer (α-10) was found to be cytotoxic, whereas theβ-anomer (β-10) was inactive.Keywords
This publication has 9 references indexed in Scilit:
- A Facile Synthesis of 4′-Thio-2′-deoxypyrimidine Nucleosides and Preliminary Studies on Their PropertiesNucleosides and Nucleotides, 1993
- Conformation of two 4'-thio-2'-deoxynucleoside analogs studied by 5000-MHz proton NMR spectroscopy and x-ray crystallography.Journal of the American Chemical Society, 1992
- 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′-thionucleosidesCarbohydrate Research, 1992
- Synthesis and anti-HIV activity of 4'-thio-2',3'-dideoxynucleosidesJournal of Medicinal Chemistry, 1992
- Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosidesJournal of Medicinal Chemistry, 1991
- 4′-Thioadenosine as a Novel Inhibitor of S-Adenosylhomocysteine Hydrolase and an Inducer for the Differentiation of HL-60 Human Leukemia CellsPublished by Springer Nature ,1986
- Some aspects of regio-, stereo-, and chemoselective reactions in carbohydrate chemistryPublished by Walter de Gruyter GmbH ,1984
- An alternative synthesis of anomeric methyl 2-deoxy-4-thio-D-erythro-pentofuranosidesThe Journal of Organic Chemistry, 1976
- STUDIES ON THE BIOCHEMICAL BASIS FOR THE ANTIVIRAL ACTIVITIES OF SOME NUCLEOSIDE ANALOGS*Annals of the New York Academy of Sciences, 1975