Mineralocorticoid activity of 21-deoxyaldosterone derivatives: Structure-function studies

Abstract

The synthesis of 21-deoxyaldosterone was undertaken to determine whether it has a possible role as a mineralocorticoid antagonist in human metabolism. It was found that the synthetic 11,18-hemiacetal form of 21-deoxyaldosterone could be converted to a 20-methyl ether when exposed to silica gel and methanol during high performance liquid chromatography. The preparation of a 11,18-acetal-18,20 hemiketal isomer and other derivatives of 21-deoxyaldosterone are described and proton n.m.r. data presented. The 20-methyl ether of 21-deoxyaldosterone has one third the affinity of aldosterone for rat kidney mineralocorticoid receptors; on bioassay, however, it shows only ~ 1% the agonist activity of a..