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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)
Author(s) -
Zhuang Yan,
Zapp Josef,
Hartmann Rolf W.
Publication year - 1997
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19973301108
Subject(s) - chemistry , stereochemistry , enzyme , wittig reaction , microsome , naphthalene , lyase , organic chemistry
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.