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Synthesis of New Trisubstituted 4‐Aminopiperidines as PAF‐Receptor Antagonists
Author(s) -
Benmehdi Houcine,
Lamouri Aazdine,
Serradji Nawal,
Pallois Frédérique,
Heymans Françoise
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700667
Subject(s) - chemistry , nitrile , diastereomer , regioselectivity , stereochemistry , antagonist , carbamate , receptor , organic chemistry , biochemistry , catalysis
Two novel classes of 4‐aminopiperidines substituted in the 3‐position by groups bearing either a carbamate or a ureido function have been synthesized from ethyl 4‐oxo‐3‐piperidinecarboxylate and 3,3′‐iminobis(propanenitrile), respectively. The key step in this synthesis, the reduction of the piperidinic β‐enamino ester or nitrile, occurred readily. In contrast to published works, the free primary amines could be isolated from the corresponding β‐amino ester or nitrile. Regioselective amidification of the amino group offered two pairs of diastereoisomers which were successfully separated and identified. Measurement of PAF‐receptor antagonist activity gave interesting results with an IC 50 close to the micromolar.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)