Abstract
The article describes the results of semiempirical quantum-chemical calculations for a series of 3',5'-esters of 5-bromo-2'-deoxyuridine with amino acids or peptides. These compounds were synthesized and tested for antiviral activity as potential prodrugs of the parent 5-bromonucleoside. It was not clear why only some of the compounds were active. On the basis of structure investigation and the calculated molecular descriptors, it was found that the determining factor for obtaining appropriate prodrugs of 5-bromo-2'-deoxyuridine is the lipophilicity of the esters.
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