Reactions of 2-acyloxyisobutyryl halides with nucleosides. 7. Synthesis and biological evaluation of some 2,2'-anhydro-1-(3',5'-di-O-acyl-.beta.-D-arabinofuranosyl)cytosine hydrochlorides

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Abstract
The direct acylation of 2,2''-anhydro-1-(.beta.-D-arabinofuranosyl)cytosine hydrochloride (cycloC) with a homologous series of saturated and unsaturated acyl chlorides in dimethylacetamide was investigated. Such acylation reactions made available a considerable number of 3'',5''-diesters of cycloC that were examined for biological activities. The compounds show cytotoxicity against HeLa [human cervical cancer] cells in tissue culture and, with the exception of the highly insoluble long-chain diesters (C16-C22), show pronounced activity against vaccinia and herpes simplex viruses. Against L1210 leukemia in mice the compounds show varied activities, the C12-C14 saturated diesters and the C18-C22 unsaturated diesters being highly effective. Other diesters, varying by only a few methylene groups, show dramatically different results.

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