292059-30-4Relevant articles and documents
Synthesis of N-substituted piperidine-4-(benzylidene-4-carboxylic acids) and evaluation as inhibitors of steroid-5α-reductase type 1 and 2
Picard, Franck,Baston, Eckhard,Reichert, Wolfgang,Hartmann, Rolf W.
, p. 1479 - 1487 (2007/10/03)
The synthesis of N-substituted piperidine-4-(benzylidene-4-carboxylic acids) is described [benzoyl (1Scheme 2Synthetic strategy.), benzyl (2), adamantanoyl (3), cyclohexanoyl (4), cyclohexylacetyl (5), diphenylacetyl (6), dicyclohexylacetyl (7), 2-propylpentanoyl (8), diphenylcarbamoyl (9), trimethylacetyl (10), 3,3-dimethylacryloyl (11), dicyclohexylacetyl derivative of the benzyl compound (12)]. Compounds were tested for inhibitory activity toward 5α-reductase isozymes 1 and 2 in human and rat. The test compounds inhibited 5α-reductase, showing a broad range of inhibitory potencies. In rat, compounds 6 (IC50=3.44 and 0.37 μM for type 1 and 2, respectively) and 9 (IC50=0.54 and 0.69 μM for type 1 and 2, respectively) displayed the best inhibition toward both isozymes. Compound 7 showed a strong inhibition toward type 2 human and rat enzyme (IC50=60 and 80 nM) but only a moderate activity versus type 1 enzyme (IC50 approximately 10 μM for rat and human enzyme). In vivo, selected compounds reduced prostate weights in castrated testosterone treated rats. Copyright (C) 2000 Elsevier Science Ltd.
