C-5'-Triazolyl-2'-oxa-3'-aza-4'a-carbanucleosides: Synthesis and biological evaluation

Roberto Romeo; Caterina Carnovale; Salvatore V Giofrè; Maria A Chiacchio; Adriana Garozzo; Emanuele Amata; Giovanni Romeo; Ugo Chiacchio

doi:10.3762/bjoc.11.38

C-5'-Triazolyl-2'-oxa-3'-aza-4'a-carbanucleosides: Synthesis and biological evaluation

Beilstein J Org Chem. 2015 Mar 9:11:328-34. doi: 10.3762/bjoc.11.38. eCollection 2015.

Authors

Roberto Romeo¹, Caterina Carnovale¹, Salvatore V Giofrè¹, Maria A Chiacchio², Adriana Garozzo³, Emanuele Amata², Giovanni Romeo¹, Ugo Chiacchio²

Affiliations

¹ Dipartimento Scienze del Farmaco e dei Prodotti per la Salute, University of Messina, Via S.S. Annunziata, 98168 Messina, Italy.
² Dipartimento di Scienze del Farmaco, University of Catania, Via A. Doria 6, 95125-Catania, Italy.
³ Dipartimento di Scienze Bio-Mediche, University of Catania,Via Androne 81, 95124 Catania, Italy.

Abstract

A novel series of 2'-oxa-3'-aza-4'a-carbanucleosides, featured with a triazole linker at the 5'-position, has been developed by exploiting a click chemistry reaction of 5'-azido-2'-oxa-3'-aza-4'a-carbanucleosides with substituted alkynes. Biological tests indicate an antitumor activity for the synthesized compounds: most of them inhibit cell proliferation of Vero, BS-C-1, HEp-2, MDCK, and HFF cells with a CC50 in the range of 5.0-40 μM. The synthesized compounds do not show any antiviral activity.

Keywords: 1,3-dipolar cycloaddition; 2’-oxa-3’-aza-4’a-carbanucleoside analogs; antitumor activity; click chemistry; nucleic acids.