Fused pyrimidines. 7. Nucleosides of pyrimidopyrimidinediones and pteridinediones as potential chemotherapeutic agents

✍ Scribed by A. Nagarajan; Bernard R. Meltsner; Thomas J. Delia

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 474 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340532

✦ Synopsis

Abstract

Several nucleoside derivatives of pyrimido[4,5‐d]pyrimidine‐2,4(1__H__,3__H__)‐dione 1 and 2,4{1__H__,3__H__‐pteridinedione 2 were prepared. Treating the appropriate silylated nucleobase with 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofura‐nose 3 in the presence of trimethylsilyl Inflate gave 4 and 8 which, upon debenzoylation, gave 5 and 9, respectively. Treatment of 4 with phosphorus pentasulfide afforded the sulfur substituted compound 6. Again, deprotection gave 7. The arabinose derivatives were obtained by treating 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐D‐arabinofuranose 10 with the silylated nucleobases to give 11 and 13. Debenzoylation gave the free arabinonucleosides 12 and 14 respectively. The deoxy derivative 16 was prepared by the reaction of 1 with 1‐chloro‐3,5‐di‐O‐acetyl‐2‐deoxy‐D‐ribofuranose 15. Deacetylation of 16 with methanolic ammonia gave the α‐anomer 17.