Konstitution und Eigenschaften des Biphenylen‐(4.4′)‐bis‐[methyl‐atropiniumbromids], einer biquartären Atropinverbindung

Szendey, G. L.; Munnes, Siegfried

doi:10.1002/cber.19610940106

Cited by 5 publications

(2 citation statements)

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“…[21][22][23][24] The 4-substituted pyridines and quinolines were synthesized from 4-chloropyridine or 4-chloroquinoline using a previously reported method. These bis-cationic compounds contain a linker and two cationic ends that are 4-substituted pyridinium or quinolinium rings with cyclic or acyclic amino groups (compounds 8-17).…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of starting materials: 3,3'-Bis(bromomethyl)biphenyl, [21] 4,4'-bis(bromomethyl)biphenyl, [22,22] bis-p-(bromomethyl)dibenzyl, [24] 1,4-bis[p-(bromomethyl)phenyl]butane, [25] 4-substituted pyridines [14,16] and 4-substituted quinolines [14,31] were synthesized according to literature procedures. 1,3-Bis(bromomethyl)benzene, and 1,4-bis(bromomethyl)benzene were purchased from Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

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Novel 4‐Amino Bis‐pyridinium and Bis‐quinolinium Derivatives as Choline Kinase Inhibitors with Antiproliferative Activity against the Human Breast Cancer SKBR‐3 Cell Line

et al. 2012

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Choline kinase (ChoK) is the first enzyme in the CDP-choline pathway that synthesizes phosphatidylcholine, the major phospholipid in eukaryotic cell membranes. Human ChoK has three isoforms: ChoKα1, α2, and β. Specific inhibition of ChoKα has been reported to selectively kill tumor cells. In this study, ten new symmetrical bis-pyridinium and bis-quinolinium derivatives were synthesized and tested for their ability to inhibit human ChoKα2. These compounds have electron-releasing groups at position 4 of the pyridinium or quinolinium rings. 1,1'-[(Butane-1,3-diylbis(benzene-1,4-diylmethylene)]bis[4-(4-bromo-N-methylanilino)pyridinium)] dibromide and 1,1'-(biphenyl-3,3'-diylmethylene)bis[7-chloro-4-(perhydroazepine-1-yl)quinolinium] dibromide were identified as highly potent ChoK inhibitors with IC(50) values of 80 nM. Kinetic enzymatic assays indicated a mixed and predominantly competitive mechanism of inhibition for these compounds, which exhibited strong antiproliferative activity (EC(50) 1 μM) against the human breast cancer SKBR3 cell line.

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Section: Resultsmentioning

confidence: 99%