4921-51-1Relevant articles and documents
Free radical polymerization of caffeine-containing methacrylate monomers
Nelson, Ashley M.,Hemp, Sean T.,Chau, Jessica,Long, Timothy E.
, p. 2829 - 2837 (2015)
The incorporation of acrylic functionality into caffeine enables the preparation of a vast array of novel thermoplastics and thermosets. A two-step derivatization provided a novel caffeine-containing methacrylate monomer capable of free radical polymerization. Copolymers of 2-ethylhexyl methacrylate and caffeine methacrylate (CMA) allowed for a systematic study of the effect of covalently bound caffeine on polymer properties. 1H NMR and UV-vis spectroscopy confirmed caffeine incorporation at 5 and 13 mol %, and SEC revealed the formation of high molecular weight (co)polymers (>40,000 g/mol). CMA incorporation resulted in a multistep degradation profile with initial mass loss closely correlating to caffeine content. Differential scanning calorimetry, rheological, and thermomechanical analysis demonstrated that relatively low levels of CMA increased the glass transition temperature, resulting in higher moduli and elucidating the benefits of incorporating caffeine into polymers.
Aza-analogs of 8-styrylxanthines as A(2A)-adenosine receptor antagonists
Mueller, Christa E.,Sauer, Roland,Geis, Uli,Frobenius, Wolfram,Talik, Przemyslaw,Pawlowski, Muciej
, p. 181 - 189 (2007/10/03)
In the present study we synthesized aza-analogs of 8-styrylxanthines, in which the ethenyl bridge is replaced by an imine, amide, or azo function, in order to investigate structure-activity relationships of the 8-substituent of A(2A)-selective xanthine derivatives. Thus, various 8-substituents were combined with theophylline or caffeine, respectively, and affinities of the novel compounds for adenosine A1- and A(2A)-receptors were determined and compared with those of analogous 8-styrylxanthine derivatives. 8-(Benzylideneamino)caffeine derivatives exhibited high affinity and selectivity for A(2A)-adenosine receptors, but were unstable in aqueous buffer solution at physiological pH values. 8-(Phenylazo)caffeine derivatives were less potent than corresponding 8-styrylcaffeine derivatives at adenosine receptors. The most potent azo compound of the present series was 8-(m-chlorophenylazo)caffeine (14b) exhibiting a K(i) value of 400 nM at A(2A)-adenosine receptors and 20-fold selectivity versus A1-receptors. Due to the facile synthetic access to 8-(phenylazo)xanthine derivatives, which are obtained by coupling of 8-unsubstituted xanthines with phenyldiazonium salts, 14b may be an interesting new lead compound for the development of more potent and selective A(2A)-antagonists with azo structure.