Synthetic nucleosides and nucleotides. XVI. Synthesis and biological evaluations of a series of 1-.BETA.-D-arabinofuranosylcytosine 5'-alkyl or arylphosphates.

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Abstract
Enzymatic selective dephosphorylation of 1-.beta.-D-arabinofuranosylcytosine 3'',5''-diphosphate with nuclease-3''-nucleotidase P1 at 60.degree. for 24 h gave 1-.beta.-D-arabinofuranosylcytosine 5''-phosphate (Ara CMP) (2) in good yield. The acylation on N4- and the 2'',3''-hydroxyl groups of 2 followed by coupling with various alcohols and phenols in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride and subsequent alkaline hydrolysis afforded the title compounds (4). The resulting 32 kinds of Ara CMP alkyl or aryl esters were examined to determine their biological activities, such as antiviral activity against herpes simplex type 1 in cultured human embryonic lung fibroblast cells, growth inhibitory activity against mouse leukemic L5178Y cells in culture and antileukemic activity against [mouse leukemia] L-1210 cells in mice. Ara CMP esters were active in these assay systems.

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