Synthesis of a steroidal A ring aromatic sulfonic acid as an inhibitor of steroid 5 alpha-reductase.
The synthesis of 17 beta-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-3-sulfonic acid (3) has been accomplished. Sulfonate 3 was designed as a novel inhibitor of human steroid 5 alpha-reductase based on considerations of enzyme mechanisms, and exhibits an inhibition constant in the low nanomolar range.
Holt
D A
DA
Department of Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19406-0939.
Oh
H J
HJ
Levy
M A
MA
Metcalf
B W
BW
D058891:5-alpha Reductase Inhibitors; D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D004963:Estrenes / Q000138:chemical synthesis*; D006801:Humans; D066298:In Vitro Techniques; D008297:Male; D015394:Molecular Structure; D051381:Rats; D013045:Species Specificity
D058891:5-alpha Reductase Inhibitors; D004791:Enzyme Inhibitors; D004963:Estrenes; C068718:17-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-3-sulfonic acid