Synthesis of 1-$\beta$-D-Arabinofuranosylcytosine-5'-methylthioacetate and Evaluation of Its Inhibitory Effect on DNA Synthesis

1-$\beta$-D-Arabinofuranosylcytosine-5'-methylthioacetate의 합성 및 이의 DNA 합성애 대한 억제작용 평가

As one of the starting materials, methylthioacetyl chloride(7) was synthesized in fair yield from mercaptoacetic acid via methyl methylthioacetate(5) prepared by alkylation employing N, N'-dicyclohexyl-O-methylisourea(4). Then 1-$\beta$-D-arabinofuranosylcytosine-5'-methylthioacetate (3) was prepared by esterification of ara-C with obtained methylthioacetyl chloride and tested for inhibitory activity on DNA synthesis in the growing primary hepatocytes and hepatoma strains($H_4$-II-E and HTC cells). In these in vitro cell lines, the inhibitory effect of ara-C-MTA(3) on DNA synthesis was similar to that of its parent ara-C but slightly lower.