A gas phase theoretical study of the hydrogen bonding properties of some androgen antagonists using molecular orbital and molecular electric field mapping methods

Abstract

A number of anilides, alkenes and an indole derivative which are known to be potent anti-androgens were studied using molecular orbital (AM1) and molecular electric field mapping (MEF) techniques. Linear correlation coefficients between the MEF values near the tertiary hydroxyl groups of these molecules and the corresponding experimentally observed hydrogen bond donating abilities (log Kα, values) were found to be satisfactory. The study illustrates the usefulness of MEF mapping in predicting the hydrogen bond donating abilities of these molecules.