Synthesis of benzo[c]quinolizin-3-ones: selective non-steroidal inhibitors of steroid 5 alpha-reductase 1

A Guarna; E G Occhiato; D Scarpi; R Tsai; G Danza; A Comerci; R Mancina; M Serio

doi:10.1016/s0960-894x(98)00505-8

Synthesis of benzo[c]quinolizin-3-ones: selective non-steroidal inhibitors of steroid 5 alpha-reductase 1

Bioorg Med Chem Lett. 1998 Oct 20;8(20):2871-6. doi: 10.1016/s0960-894x(98)00505-8.

Authors

A Guarna¹, E G Occhiato, D Scarpi, R Tsai, G Danza, A Comerci, R Mancina, M Serio

Affiliation

¹ Dipartimento di Chimica Organica U. Schiff, CNR, Università di Firenze, Italy. guarna@chimorg.unifi.it

PMID: 9873639
DOI: 10.1016/s0960-894x(98)00505-8

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

5-alpha Reductase Inhibitors
Enzyme Inhibitors
Isoenzymes
Quinolizines