title: Synthesis of benzo[c]quinolizin-3-ones: selective non-steroidal inhibitors of steroid 5 alpha-reductase 1.
abstract: A short and efficient synthesis of novel benzo[c]quinolizin-3-one derivatives is described. The synthesis is based on the tandem Mannich-Michael cyclization between 2-silyloxy-1,3-butadienes and a N-t-Boc iminium ion. The prepared derivatives are selective inhibitors of human steroid 5 alpha-reductase isoenzyme 1, thus having potential application as drugs for treatment of male pattern baldness and other DHT-dependent skin disorders.
authors.affiliation: Dipartimento di Chimica Organica U. Schiff, CNR, Università di Firenze, Italy. guarna@chimorg.unifi.it
authors.forename: A
authors.initials: A
authors.lastname: Guarna
authors.forename: E G
authors.initials: EG
authors.lastname: Occhiato
authors.forename: D
authors.initials: D
authors.lastname: Scarpi
authors.forename: R
authors.initials: R
authors.lastname: Tsai
authors.forename: G
authors.initials: G
authors.lastname: Danza
authors.forename: A
authors.initials: A
authors.lastname: Comerci
authors.forename: R
authors.initials: R
authors.lastname: Mancina
authors.forename: M
authors.initials: M
authors.lastname: Serio
mesh_terms: D058891:5-alpha Reductase Inhibitors; D000505:Alopecia / Q000188:drug therapy; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D008297:Male; D011467:Prostate / Q000187:drug effects / Q000201:enzymology; D011807:Quinolizines / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D058891:5-alpha Reductase Inhibitors; D004791:Enzyme Inhibitors; D007527:Isoenzymes; D011807:Quinolizines