Theoretical studies of 5-X-2′-deoxyuracils with known antiviral activity. A comparison of molecular mechanics, AM1, and PM3 semiempirical molecular orbital calculations

Abstract

A comparative structural study of several 5-substituted-2′-deoxyuracils with known antiviral activity has been carried out. The Molecular Mechanics (MM) and semiempirical Molecular Orbitals (MO) (in the framework of the AM1 and the PM3 hamiltonians) results have been tested with data for several crystal analogues extracted from the Cambridge Structural Database (CSD). We have also calculated the electrostatic potentials in the Van der Waals surface in the neighbourhood of specific atoms. The sugar ring conformations are discussed. The results are scattered. The electrostatic potential results are not consistent enough to extract conclusions. A greater number of compounds should be investigated.