Theoretical investigations of methanesulphonamide as a hydroxy group equivalent in drugs. Examples from possible β-adrenergic agents and analysis of computational methods

Abstract

Quantum chemical methods were used to analyse various physical chemical properties and interaction characteristics of methanesulphonamide. Comparison of β-methylsulphonylaminophenethylamine with its hydroxy analogue and certain structural fragments was used to examine the structure–activity relationships of arylhydroxyethylamines. The general role of methanesulphonamide as a hydroxy replacement was examined. In particular, based on the results of the calculations presented here, the differences in proton affinities, proton-donating abilities, or conformational properties do not account for the differences in activities of these compounds. Critical evaluation was made of several quantum chemical methods used in the study of these and other possible drugs, including the semiempirical MNDO and MINDO/3 methods and the ab initio Hartree–Fock method with the STO-3G, 3-21G, and 3-21G(*) basis sets.