Synthesis of Z- and E-1-Methyl-2-(1-hydroximinoethyl)-6-methoxy-3,4-dihydronaphthalene and Evaluation as Inhibitors of 17α-Hydroxylase-C17,20-Lyase (P450 17)

✍ Scribed by Yan Zhuang; Josef Zapp; Rolf W. Hartmann

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 247 KB
• Volume: 330
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.19973301108

✦ Synopsis

Abstract

The synthesis and biological evaluation of Z‐ and E‐1‐methyl‐2‐(1‐hydroximinoethyl)‐6‐methoxy‐3,4‐dihydro‐naphthalene (Z‐1 and E‐1) as nonsteroidal inhibitors of 17α‐hydroxylase‐C17,20‐lyase (P450 17, CYP17) is described. Z‐1 and E‐1 were separated by column chromatography and identified by ^1^H NMR. The synthesis of the key compound 3 was accomplished by a new reaction acetylating the 1‐methyl‐6‐methoxy‐3,4‐dihydronaphthalene compound 2 under Friedel‐Crafts conditions. Compound 2 was obtained from the 1‐tetralone via Wittig reaction. Using a microsomal fraction of human testicular enzyme, Z‐1 and E‐1 inhibited the target enzyme only marginally.