Synthesis of New Trisubstituted 4-Aminopiperidines as PAF-Receptor Antagonists

Autor:	Houcine Benmehdi, Frédérique Pallois, Aazdine Lamouri, Françoise Heymans, Nawal Serradji
Rok vydání:	2008
Předmět:	Carbamate Nitrile Stereochemistry medicine.medical_treatment Organic Chemistry Diastereomer Antagonist Regioselectivity Biological activity chemistry.chemical_compound chemistry medicine Physical and Theoretical Chemistry Receptor IC50
Zdroj:	European Journal of Organic Chemistry. 2008:299-307
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200700667
Popis:	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 IC50 close to the micromolar.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Databáze:	OpenAIRE
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