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Synthesis and Biochemical Evaluation of (Carbamoylalkenyl)phenyloxy Carboxylic Acid Derivatives as Non‐steroidal 5α‐Reductase Inhibitors
Author(s) -
Kattner Lars,
Göhring Sigrid,
Hartmann Rolf W.
Publication year - 1995
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.19953280307
Subject(s) - chemistry , enzyme , steroid , carboxylic acid , dihydrotestosterone , potency , hyperplasia , enzyme inhibitor , in vitro , chemical synthesis , stereochemistry , prostate , ic50 , biochemistry , reductase , androgen , cancer , endocrinology , medicine , hormone , biology
Several (carbamoylalkenyl)‐ and (carbamoylalkenyl)phenyloxy carboxylic acids (Table 1) and some of their ethyl esters (Table 2) were synthesized and evaluated in vitro as inhibitors of steroid 5α‐reductase. Inhibitors of this enzyme may be useful in treating dihydrotestosterone‐related diseases such as prostate cancer and benign prostatic hyperplasia. Using an enzyme preparation obtained from human prostate carcinoma tissue, the inhibition values ranged from 0 to 57 % at the given dose of 100 μM. In the series of free acids, surprisingly, the compounds showed only modest inhibitory potency (0–26 %). By contrast, the ethyl esters displayed inhibition values up to 57 %. Structure‐activity relationships are discussed.