Design, synthesis and cytotoxic evaluation of truncated 3′-deoxy- 3′, 3′ difluororibofuranosyl pyrimidine nucleosides

Abstract

Truncated 3′-deoxy- 3′, 3′ difluororibofuranosyl pyrimidine nucleoside derivatives were synthesized from d-ribose via β-apioribo pyrimidine nucleoside intermediates 11a-c. The synthetic approach signifies that truncation at C3′ position of apioribose ring of 13a-c by oxidative cleavage of diols with Pb(OAc)4 and followed by fluorination with DAST as key steps. Cytotoxic evaluation of synthesized truncated nucleoside derivatives 16a-c and 19a-c were tested against MCF7 and MDA-MB-231 breast cancer cell lines. However, only 19a was shown minimal growth suppression activity on MDA-MB-231 cancer cell lines.