Biologically Important Nucleosides: A General Method for the Synthesis of Unsaturated Ketonucleosides of Uracil and its Analogs

Abstract A general method for the synthesis of unsaturated keto- nucleosides of a-L-rhamnose with 5-fluorouracil and their in vitro and in vivo anticancer activity evaluation results are discussed. The synthesis was effected by selective protection and deprotection of the sugar hydroxyls with acid and base labile groups following standard procedure. In the final step, oxidation of the 2′,3′ acylated nucleoside afforded the 4′-ketoenonucleoside. Two unsaturated ketonucleosides, 3′-O-benzoyl and 3′-O-acetyl were synthesized in this way and both these compounds show inhibition of tumor cell growth af murine leukemia L1210, murine mammary carcinoma FM3A, human B-lymphoblast Raji, human T-lymphoblast Molt/4F. Also one compound shows antitumor activity in the adenocarcinoma 755 model in BDF mice.