120848-76-2Relevant academic research and scientific papers
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.
Fluorous Boc (FBoc) carbamates: New amine protecting groups for use in fluorous synthesis
Luo,Williams,Read,Curran
, p. 4261 - 4266 (2007/10/03)
The first fluorous variants of the Boc (tert-butyloxycarbonyl) group have been prepared and tested for their suitability as nitrogen protecting groups. A group with two fluorous chains and an ethylene spacer, (RfCH2CH2)2(CH3)COC(O)-, was readily attached to a representative amine but was difficult to cleave. In contrast, groups with two fluorous chains and a propylene spacer, (RfCH2CH2CH2)2-(CH3) COC(O)-, or one fluorous chain and an ethylene spacer, (RfCH2CH2)(CH3)2COC(O)-, were readily formed and cleaved. The fluorous alcohol component of the FBoc group can be removed by evaporation and can be recovered and reused. The utility of the new FBoc group (C8F17CH2CH2)(CH3) 2COC(O)- was demonstrated in 16 and 96 compound library synthesis exercises. Separations can be achieved either by manual, parallel fluorous solid-phase extraction, or automated, serial fluorous chromatography. The results provide additional confirmation of the value of "light" fluorous synthesis techniques, and the new fluorous Boc groups expand the applicability of fluorous synthesis techniques to many classes of nitrogen-containing organic compounds.
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.
4-Amino-2-piperidino-quinazolines
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, (2008/06/13)
Regulators of the cardiovascular system and, in particular, in the treatment of hypertension having the formula STR1 wherein R is lower alkyl; X, is a 3- or 4-position substituent and is --(CH2)n CONR1 R2, --O(C
