Synthesis of highly cytotoxic tiazofurin mimics bearing a 2,3-anhydro function in the furanose ring

This paper describes a divergent de novo synthesis of 2-(2,3-anhydro-β-d-ribofuranosyl)thiazole-4-carboxamide (2′,3′-anhydro-tiazofurin) and the corresponding α- and β-homo-C-nucleosides. The synthetic approach was based on a multistep transformation of d-glucose into suitably protected aldonthioamides followed by their subsequent cyclocondensation with ethyl bromopyruvate to form the thiazole ring. Antiproliferative activity of the target molecules is reported against several human tumour cell lines.

Graphical abstractNovel tiazofurin derivatives, 2′,3′-anhydro-tiazofurin (2) and the corresponding β-(3) and α-(25) homo-C-nucleosides, have been synthesized and evaluated for their in vitro antitumour activity.Figure optionsDownload full-size imageDownload as PowerPoint slide