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1 2012

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Synteza analogów adenozyny

Samsel M., Dzierzbicka K.

Wiadomości Chemiczne

2012

[Z] 66, 3-4

321-340

Adenosine (Rys. 1) is a purine nucleoside playing an important role in human body. It is involved in key pathways such as purinergic nucleic acid base synthesis, amino acid metabolism and modulation of cellular metabolic status [1,2]. Adenosine acts through the four types of adenosine receptors: A1, A2A, A2B and A3 belonging to the G protein-coupled receptor family [3]. In physiological conditions this nucleoside is present in a micromolar range [5]. However, when metabolic stress occurs extracellular level of adenosine raises revealing its protective properties. Depending on an activated receptor subtype, adenosine demonstrates cardioprotective and neuroprotective activity during hypoxia or ischemia, it stimulates the immunological system [6, 7]. Besides many potential applications, adenosine is used mainly for the treatment of paroxysmal supraventricular tachycardia. Limitations are linked to a very short blood half-time and no receptor specificity [8]. This review is focused on novel literature data about synthesis of adenosine analogues with interesting biological activities. In order to influence adenosine receptor selectivity and pharmacokinetic properties a nucleoside structure can be modified in purine [14, 15, 17, 22, 26, 27, 35] or sugar ring [29, 32]. New interesting compounds are also synthesized by cyclisation of adenosine [36]. Modification of adenosine structure allowed obtaining compounds with targeted action: antiarrhythmic [11, 12], antinociceptive [9], antilipolytic [13], antiviral [29] or anticancer [35].