10.1021/jm00050a019
The research focuses on the synthesis and evaluation of 5'-acyl furanosteroids for their androgen receptor affinity and antiandrogenic activity. The purpose of this study was to develop new methods to prepare 5'-acetyl derivatives and explore the structure-activity relationships (SAR) of these compounds, aiming to understand their potential as therapeutic agents for conditions like benign prostatic hyperplasia (BPH), acne, and hirsutism. The researchers synthesized a series of 5'-acyl furanosteroids using acid anhydrides and acid chlorides, in the presence or absence of Lewis acids, and evaluated their binding affinity to the androgen receptor and their in vivo antiandrogenic and androgenic activities. The conclusions drawn from the study were that most 5'-acyl furanosteroids maintained androgen receptor affinity but displayed diminished antiandrogenic activity compared to 4,5'-methylsulfonyl furanosteroid. The biological studies revealed that these compounds were either androgens or modest antiandrogens. Electrostatic potential maps of the substructures provided insights into the lack of significant antiandrogenic activity observed in 5'-acyl furanosteroids. Chemicals used in the process included acid anhydrides, acid chlorides, Lewis acids, sodium formaldehyde sulfoxylate, palladium on carbon, and various furanosteroid derivatives.