ChemInform Abstract: Synthesis, Spectroscopic and Conformational Investigations of 10α‐Methyl Steroid Spirolactones.

Abstract

ChemInform Abstract Starting from the mixtures of the ketones (I), the spirolactone-dienone (VII) is prepared according to known procedures. This dienone (VII), on reaction with MeSH (VIII) affords a separable mixture of the isomeric 7-α-methylthio derivatives (IX) and (X), the latter being the thermodynamically more stable isomer. In order to obtain information about the structure-activity relation, the conformations of the rings A and B of the compounds (VI), (VII), (IX) and (X) are determined by CD spectrometry. The results are compared to the energetically preferred conformations calculated by semiempirical quantum mechanical calculations. The methylthio derivatives (IX) and (X) show no aldosterone antagonistic activity in in vivo and in vitro tests.