79362-49-5Relevant academic research and scientific papers
HALOPHENYL-PYRIDYL-ALLYLAMINE DERIVATIVES AND USE
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, (2008/06/13)
Compounds of the formula: wherein R is H or CH3, n is 1 or 2 and X is F, Cl, Br, I bound in an optional position to the phenyl group, provided that when X is Br it is bound in a position other than the 4 position, processes for their preparation and pharm
Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake
Hogberg,Ulff,Renyi,Ross
, p. 1499 - 1507 (2007/10/02)
Analogues of the antidepressant agent zimelidine [6, (Z)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine], a selective inhibitor of neuronal 5-hydroxytryptamine reuptake, were synthesized by several routes with the aim of obtaining compounds having a cis configuration (with respect to pyridyl and allylamine). Two methods utilized suitably substituted benzoylpyridines as starting materials. In two other routes, the bromine in 6 was either directly displaced (CN) or converted via the corresponding lithio derivative to H, Cl, I, Me, SiMe3. The configurations were determined by UV, 1H NMR and lanthanide-induced shifts in 1H NMR. The compounds were evaluated as uptake inhibitors by measuring the accumulation of [3H]noradrenaline and 5-hydroxyl[14C]tryptamine in mouse brain slices (in vitro and in vivo). Para substitution favored 5-hydroxytryptamine activity and ortho substitution favored NA activity in the cis series. The in vitro effect on 5-hydroxytryptamine was rather insensitive to variations in the para substituent, whereas pronounced effects in vivo were observed only with Cl, Br (6), and I.
