29820-77-7Relevant academic research and scientific papers
Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds
Nabuurs, Rob J.A.,Kapoerchan, Varsha V.,Metaxas, Athanasios,Hafith, Sarah,de Backer, Maaike,Welling, Mick M.,Jiskoot, Wim,van den Nieuwendijk, Adrianus M.C.H.,Windhorst, Albert D.,Overkleeft, Herman S.,van Buchem, Mark A.,Overhand, Mark,van der Weerd, Louise
, p. 6139 - 6148 (2016/11/30)
Detection of cerebral β-amyloid (Aβ) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential Aβ imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower Log?P values, and studied their fluorescent properties and Aβ binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for Aβ plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a Log?P value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl)benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents.
Anil-Synthese. 22 Mitteilung. Ueber die Herstellung von Styryl und Distyryl-Derivaten des Pyridins
Siegrist, Adolf Emil,Meyer, Hans Rudolf,Gassmann, Peter,Moss, Serge
, p. 1311 - 1334 (2007/10/02)
2,4-, 2,5- and 2,6-Dimethylpyridines react with anils of aromatic aldehydes in the presence of dimethylformamide and potassium hydroxide to yield the corresponding distyrylpyridines ('anil synthesis').Under the same reaction conditions (4-methylstyryl)pyridines are converted to (stilbenylvinyl)pyridines.Similarly, the Schiff's base derived from pyridine-3-carbaldehyde and chloranile on treatment with methyl- and p-tolyl-substituted aromatic hetericycles gives the corresponding (heteroaryl-styryl)pyridines, whereas with the Schiff's bases derived from pyridine-2= and -4-carbaldehyde side reactions, such as dimerization followed by disproportionation predominate.
