Collect. Czech. Chem. Commun. 2006, 71, 691-697

Quantum-Chemical Investigations of 5-Bromo-2'-Deoxyuridine Derivatives with Antiviral Activity

Zhivko A. Velkova,*, Yasen Zh. Velkovb, Alia V. Tadjerb and Ivanka G. Stankovaa

a Department of Chemistry, South West University "Neophit Rilsky", 66 Ivan Mihajlov Str., 2700-Blagoevgrad, Bulgaria
b Department of Physical Chemistry, Sofia University "St. Kliment Ohridsky", Faculty of Chemistry, 1 James Bourchier, Blvd., 1164 Sofia, Bulgaria


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.

Keywords: Quantum chemistry; Semiempirical calculations; Nucleosides; Antivirals; Prodrugs; Amino acids; Peptides; Lipophilicity.

References: 20 live references.