S. Landvatter, J. Katzenellenbogen
Nov 1, 1982
Citations
0
Influential Citations
31
Citations
Quality indicators
Journal
Journal of medicinal chemistry
Abstract
A series of nonsteroidal, side-chain functionalized estrogens based on (3R*,4S*)-3,4-bis(4-hydroxyphenyl)hexane (hexestrol) and (2R*,3S*)-2,3-bis(4-hydroxyphenyl)pentane (norhexestrol) has been prepared; these include amide, diazo ketone, ester, alcohol, ketone, fluoro, bromo, iodo, and saturated hydrocarbon derivatives. Analysis of the binding affinity of these compounds to the uterine estrogen receptor, measured by competitive binding assay, reveals trends that can be related to the steric size, the hydrophobicity, and the hydrogen bond accepting character of the side-chain substituents. Comparison of binding affinities between norhexestrol and hexestrol derivatives indicates that, in general, the norhexestrols show significantly higher receptor binding affinities, making this series of compounds ideally suited as functional probes for the estrogen receptor.