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: A Guarna, E G Occhiato, D Scarpi, R Tsai, G Danza, A Comerci, R Mancina, M Serio
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 8 Issue 20 Pg. 2871-6 (Oct 20 1998) ISSN: 0960-894X [Print] England
• PMID: 9873639 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 5-alpha Reductase Inhibitors
• Enzyme Inhibitors
• Isoenzymes
• Quinolizines

Topics

• 5-alpha Reductase Inhibitors
• Alopecia (drug therapy)
• Enzyme Inhibitors (chemical synthesis, pharmacology)
• Humans
• Inhibitory Concentration 50
• Isoenzymes (antagonists & inhibitors)
• Male
• Prostate (drug effects, enzymology)
• Quinolizines (chemical synthesis, pharmacology)