The melting point was determined in a capillary tube in Electrothermal 9150 equipment. Following with our interest about the studies of new 8-fenoxi caffeine derivatives we report in this paper the synthesis and the crystal structure of 8- (4-bromophenoxy) caffeine.Ĭommercially available starting materials and reagents for synthesis were acquired from commercial sources (Fluka, Merck and BDH), and were used without additional purification. Their remarkable biological activities and novel structure features have stimulated many laboratories to the synthesis and the study of the relationship between molecular structure and biological activity ( Romero-Hernández, 2016). Such compounds also have activity as analgesics, anti-inflammatories, behavioral stimulants, diuretics ( Tavares and Sakata, 2012).Ī large number of derivatives and analogues were subsequently synthesized and evaluated as AR antagonists ( Mitkov et al., 2007 Georgieva et al., 2014. Such xanthines and other caffeine-inspired heterocycles now provide important research tools and potential therapeutic agents for intervention in Alzheimer’s disease, asthma, cancer, diabetes, and Parkinson’s disease. Caffeine and various analogs, the latter designed to enhance potency and selectivity toward specific biological targets, have played key roles in defining the nature and role of adenosine receptors, phosphodiesterases, and calcium release channels in physiological processes. Despite the widespread use of caffeine, it still has the ability to surprise, mostly in relation to its biological activity ( Agyemang and Oppong, 2013 Ribeiro and Sebastiao, 2010 Waldvogel, 2003) but not only, recently scientists from the University of California, Los Angeles (UCLA), and Solargiga Energy in China have reported that caffeine improves the performance and thermal stability of perovskite solar cells their research shows that caffeine can help make apromising alternative to traditional solar cells more efficient at converting light to electricity ( Wang and Jingjing, 2019).Ĭaffeine was the first adenosine receptor (AR) antagonists described in the literature and also has an influence on an extended set of biological process ( Muller and Jacobson, 2011) There are several known mechanisms of action to explain the effects of caffeine the most prominent is that it reversibly blocks the action of adenosine on its receptor and consequently prevents the onset of drowsiness induced by adenosine ( Ribeiro et al., 2002, Rogozin et al., 2008). Palabras clave: estructura cristalina, análogos de la cafeína, síntesis, reacción de Ullmann, difracción de rayos X, derivados de la 8-fenoxicafeína.Ĭaffeine is a central nervous system stimulant of the methylxanthine class, and it is the world’s most widely consumed psychoactive drug ( Daly, 2007). El empaquetamiento de las moléculas está orientado de forma antiparalela. La estructura está formada de moléculas discretas, las cuales presentan un puente de hidrógeno intramolecular entre un átomo de hidrógeno del grupo metilo del anillo imidazol, y el átomo de oxígeno del grupo carbonilo. El grupo cafeína tiene un ángulo diedro de 58.18(9)o con el grupo bromofenoxi. El compuesto cristaliza en el grupo espacial ortorrómbico P212121, y posee los siguientes parámetros cristalográficos: a= 7.9056(3), b= 9.1413(3), c= 20.2023(6) Å, Z=4. Se reporta la síntesis y la estructura cristalina absoluta determinada por técnicas de monocristales del 8- (4-bromofenoxi) cafeína. Keywords: crystal structure, caffeine analogs, synthesis, Ullmann’s reaction, X-ray diffraction, 8-fenoxycaffeine derivatives. The packing of the molecules is oriented in an anti-parallel fashion. The caffeine group makes a dihedral angle of 58.18(9) º with the bromofenoxy moiety The structure consists of discrete molecule with weak intramolecular hydrogen bond between hydrogen of the methyl group of imidazole ring and oxygen atom of the carbonyl group. The title compound crystallizes in the orthorhombic space group P2.2.2. 8- (4-bromophenoxy) caffeine was synthesized, and its absolute crystal structure was determined by single crystal techniques.
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