title: Synthesis of a steroidal A ring aromatic sulfonic acid as an inhibitor of steroid 5 alpha-reductase.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19406-0939.
authors.forename: D A
authors.initials: DA
authors.lastname: Holt
authors.forename: H J
authors.initials: HJ
authors.lastname: Oh
authors.forename: M A
authors.initials: MA
authors.lastname: Levy
authors.forename: B W
authors.initials: BW
authors.lastname: Metcalf
mesh_terms: 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
chemical_list: D058891:5-alpha Reductase Inhibitors; D004791:Enzyme Inhibitors; D004963:Estrenes; C068718:17-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-3-sulfonic acid