Synthesis of benzo[c]quinolizin-3-ones: selective non-steroidal inhibitors of steroid 5 alpha-reductase 1.
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.
Guarna
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Dipartimento di Chimica Organica U. Schiff, CNR, Università di Firenze, Italy. guarna@chimorg.unifi.it
Occhiato
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Scarpi
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Tsai
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Danza
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Comerci
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Mancina
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Serio
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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
D058891:5-alpha Reductase Inhibitors; D004791:Enzyme Inhibitors; D007527:Isoenzymes; D011807:Quinolizines