58574-55-3

Upstream product

• 77744-08-2 α-ethenyl-α-phenyl-3-pyridinemethanol 
• 70263-43-3 1-(4-Bromophenyl)-1-(3-pyridyl)-2-propen-1-ol 
• 77744-15-1 Acetic acid 1-phenyl-1-pyridin-3-yl-allyl ester 
• 124-40-3 dimethyl amine 
• 56775-88-3 Zimelidine 

Relevant academic research and scientific papers

Synthesis of 3-Aryl-3-pyridylallylamines Related to Zimelidine via Palladium-Catalyzed Amination

Reaction of aryl pyridyl ketones 1 with vinylmagnesium bromide followed by acetylation of the products 2 with acetic anhydride/Et3N and with 4-(dimethylamino)pyridine (DMAP) as a catalyst gave acetates 3 in high yields.Treatment of acetates 3 with dimethylamine in the presence of a palladium catalyst produced a mixture of E and Z isomers of 3-aryl-3-pyridylallylamines 4.

Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake

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.