Issue 4, 1990

The synthesis of 4-alkylsulphonyl-5-amino- and 5-amino-4-phosphono-imidazole nucleosides as potential inhibitors of purine biosynthesis

Abstract

Conversion of 4(5)-methylthio-5(4)-nitroimidazole (11) into its silyl derivative and subsequent condensation with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (9) in the presence of trimethylsilyl trifluoromethanesulphonate for a short reaction time gave 4-methylthio-5-nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (15) with high regioselectivity; use of longer reaction times gave predominantly the 5-methylthio-4-nitro-isomer (14). 5-Amino-4-methylsulphonyl-1-β-D-ribofuranosyl)imidazole (7) was obtained from (15) in three steps.

Similar chemistry was used to prepare 5-amino-4-[(carboxamido)methyl]sulphonyl-1 -β-D-ribofuranosylimidazole (8), 5-[(diethylphosphono)methyl]thio-4-nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (26), and 4-{[2,3-bis(methoxycarbonyl)propyl]thio}-5-nitro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (29).

Desulphurization of 3′,5′-di-O-t-butyldimethylsilyl-β-D-arabinofurano[1′,2′ : 4,5]oxazolidine-2- thione (33) and subsequent interaction with diethyl α-amino-cyanomethyl phosphonate (32) gave, after desilylation, 5-amino-4-diethylphosphono-1-(β-D-arabinofuranosyl)imidazole (36).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1990, 955-963

The synthesis of 4-alkylsulphonyl-5-amino- and 5-amino-4-phosphono-imidazole nucleosides as potential inhibitors of purine biosynthesis

J. G. Buchanan, A. E. McCaig and R. H. Wightman, J. Chem. Soc., Perkin Trans. 1, 1990, 955 DOI: 10.1039/P19900000955

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements