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Title: New substituted 1, 3, 7, 8-xanthines as potent adenosines receptor ligands


A new series of aza-analogs of 8-styryxanthines was synthesized, were the ethenyl bridge is replaced by imine (1-6) or azo (7-12) function, in order to investigate structure-activity relationships of the 8-substituent of A2A-selcctive xanthine derivatives. Thus, various 8-substituents were combined with theophyllinc or caffeine, respectively, and affinities of the novel compounds for adenosine A1- and A2A- receptors were determined and compared with those of analogous 8-styrylxanthine derivatives. In general, series of l-12 derivatives were less patent than corresponding 8-strylcaffcine but due to the facile synthetic access to 8-phenylazoxanthine derivatives, they may be an interesting new lead compounds for the development of more potent and selective A2A-antagonists with azo structure. Next synthetic approach was to introduce aminopropyl or N,N-dimethylaminopropyl substituents into 3-position of the 1-metyl-, 1-propyl- or 1- propargylxanthine ring. The hydrochlorides salts (60-72) are well water-soluble and they arc under further investigations. They will be tested in radioligand binding assays for affinity to A1 and A2A adenosine receptors. The chemical structures were confirmed by elementary analysis and spectral methods: 1H-NMR and MS. Compounds 6 and 10 were investigated by means of X-ray powder diffractometry and the crystal structures were solved from laboratory diffra ; ctometer data. There were made conformation analysis of those compounds by molecular modelling methods as well. Purity and homogeneity was investigated by TLC method.

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2 - studia doktoranckie

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Wydział Farmaceutyczny


Pawłowski, Maciej

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tylko w bibliotece

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Jul 21, 2022

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Nov 21, 2012

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ZB-108271 Jul 21, 2022


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