Synthesis and Stability Studies of 2′,3′,5′-tri-O-Acetyl-2-Amino(-N⁶-Cyclopentyl)-1-Deazaadenosines

Abstract

In this article, we report on the synthesis of 2′,3′,5′-tri-O-acetyl-2-amino-1-deazaadenosine and of 2′,3′,5′-tri-O-acetyl-2-amino-N ⁶ -cyclopentyl-1-deazaadenosine, which are very versatile intermediates for the preparation of 2-substituted 1-deazaadenosine derivatives. The two synthesized compounds showed to be quite unstable, with the N ⁶ -substituted derivatives being less stable than the N ⁶ -unsubstituted counterpart, according to the calculated HOMO-LUMO energy gap. Stability studies were performed through HPLC-MS analysis.

Keywords:

• Stability studies
• I-deazaadenosine
• HOMO-LUMO energy gap

Authors gratefully acknowledge financial support by Fondo di Ateneo per la Ricerca (University of Camerino) and by grants from the Italian Ministry of Research: FIRB 2001 and FIRB 2003.