Electronic-topological study of the structure-activity relationships in a series of steroids with mineralocorticoid binding affinity

Abstract

Conformational analysis and quantum chemical calculations were carried out using molecular mechanics (MMP2) and semi-empirical quantum chemistry (CNDO/2) methods for 51 steroid homologues belonging to a series of 17-spirolactones. Matrices called Electronic-Topological Matrices of Conjunction (ETMCs) were formed using data obtained from quantum chemical calculations. A structural fragment of activity was identified in the series of steroids. As seen from the fragment's properties, active compounds are characterized by the presence of two atoms of oxygen, O-1 and O-3, which are situated at a distance of 13.5 Angstrom and possess high negative charges (-0.29 to -0.31 (e) over bar).