The synthesis of 5-carboxamido-4-hydroxy-3-(β-D-ribofuranosyl)-thiophene derivatives, analogues of pyrazofurin

✍ Scribed by L. Huybrechts; D. Buffel; E. Freyne; G. Hoornaert

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 643 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)83500-6

✦ Synopsis

Methyl 5-carboxamido-4-hydroxy-3(B-D-ribofuranosyl)-2-thiophene carboxylate 2a and the corresponding 2.,5-thiophene dicarboxamide 2b, two new analogues of-the antiviral compound pyrazofurin, were synthesized: A base mediated condensation method with dimethyl thiodiacetate and methyl 2(2,3,5r tri-0-~-butyldimethylsilyl-B-D-ribofuranosyl)-2-oxoacetate 5 was used. The structure of these compounds and their intermediates was determined spectroscopically. The occurrence in nature of a number of C-glycosyl nucle&ides, many of which show biological activity, stimulated a lot of research on this type of compounds. 1 The natural C-nucleoside pyrazofurin 1, 2 characterized by a broad spectrum antiviral 3a,b and antitumor activity 3c at low concentrations, was synthesized by four groups. 4 However in viva experiments with 1. &owed significant