120848-76-2Relevant articles and documents
Improving selectivity preserving affinity: New piperidine-4-carboxamide derivatives as effective sigma-1-ligands
Zampieri, Daniele,Laurini, Erik,Vio, Luciano,Fermeglia, Maurizio,Pricl, Sabrina,Wunsch, Bernhard,Schepmann, Dirk,Mamolo, Maria Grazia
, p. 797 - 808 (2015/02/19)
We report the design, synthesis and binding evaluation against 1 and 2 receptors of a series of new piperidine-4-carboxamide derivatives variously substituted on the amide nitrogen atom. Specifically, we assessed the effects exerted on receptor affinity by substituting the N-benzylcarboxamide group present on a series of compounds previously synthesized in our laboratory with different cyclic or linear moieties. The synthesized compounds 2a-o were tested to estimate their affinity and selectivity toward 1 and2 receptors. Very high 1 affinity (Ki Combining double low line 3.7 nM) and Ki2/Ki1 selectivity ratio (351) were found for the tetrahydroquinoline derivative 2k, featuring a 4-chlorobenzyl moiety linked to the piperidine nitrogen atom.
2-((4-Piperidyl)methyl)-1,2,3,4-tetrahydroisoquinoline derivatives, their preparation and their application in therapy
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, (2008/06/13)
A compound of formula (I) STR1 in which R is (a) a hydrogen atom; (b) a linear or branched (C1 -C6) alkyl group; an allyl group; a cycloalkylmethyl group in which the cycloalkyl moiety has from 3 to 6 carbon atoms; a phenylmethyl group unsubstituted or substituted with one to three substituents chosen from halogen atoms and trifluoromethyl, nitro, amino, dimethylamino, cyano, aminocarbonyl, linear or branched (C1 -C3) alkyl, linear or branched (C1 -C3) alkoxy and linear or branched (C1 -C3) alkylthio groups; a 2-phenylethyl group; a 3-phenylpropyl group; a 3-phenyl-2-propenyl group; a phenylcarbonylmethyl group; a naphthylmethyl group; a pyridylmethyl group; a furylmethyl group; or a thienylmethyl group; or (c) a linear or branched (C2 -C6) alkanoyl group; a cycloalkylcarbonyl group in which the cycloalkyl moiety has from 3 to 6 carbon atoms; a trifluoroacetyl group; a phenyl-carbonyl group unsubstituted or substituted with one to three substituents chosen from halogen atoms and trifluoromethyl, nitro, linear or branched (C1 -C3) alkyl, linear or branched (C1 -C3) alkoxy and linear or branched (C1 -C3) alkylthio groups; a 1-oxo-3-phenyl-2-propenyl group; a naphthylcarbonyl group; a pyridylcarbonyl group; a furylcarbonyl group; a thienylcarbonyl group; a (2-indolyl)-carbonyl group; or a (5-indolyl)carbonyl group; or a pharmacologically acceptable acid addition salt thereof.