Collect. Czech. Chem. Commun. 2006, 71, 1088-1098

Purine and Pyrimidine Nucleoside Analogs of 3'-C-Methyladenosine as Antitumor Agents

Loredana Cappellaccia, Palmarisa Franchettia, Riccardo Petrellia, Sara Riccionia, Patrizia Vitaa, Hiremagalur N. Jayaramb and Mario Grifantinia,*

a Dipartimento di Scienze Chimiche, Università di Camerino, 62032 Camerino, Italy
b Department of Biochemistry and Molecular Biology, Indiana University School of Medicine and Richard Roudebush VA Medical Center, Indianapolis, IN 46202, U.S.A.


3'-C-Methyladenosine (3'-Me-Ado) is a mechanism-based ribonucleotide reductase inhibitor endowed with antitumor activity against both human leukemia and carcinoma cell lines. In this paper, we report the synthesis and antitumor evaluation of a series of purine and pyrimidine 3'-C-methylribonucleoside analogs of 3'-Me-Ado. A stereoselective synthesis of the arabino analog of 3'-Me-Ado is also described. Among the tested compounds, only 3'-C-methyluridine showed moderate antitumor activity against human myelogenous leukemia K562 cell line.

Keywords: Antimetabolites; Purines; Nucleosides; Pyrimidines; C-Branched nucleosides; 3'-C-Methyl-β-D-ribonucleosides; Cytoxicity.

References: 14 live references.