Nukleozydy 8-azapurynowe : synteza i aktywność biologiczna
Journal Title: Wiadomości Chemiczne - Year 2017, Vol 71, Issue 3
Abstract
The synthetic approaches to 8-azapurine nucleosides and their biological activities have been reviewed. This class of compounds could serve as antimetabolites of purine nucleoside with potential clinical applications [1–6]. They were primarily synthesized by glycosylation of 8-azapurines, which could be easily prepared from appropriately substituted 4,5-diaminopyrimidines when reacted with nitric(III) acid [1]. Since in 8-azapurines at least three nitrogen atoms could serve as nucleophilic centers the regiochemistry of glycosylation was discussed in details. Generally, mixtures of N9, N8 and N7-substituted 8-azapurine nucleosides were formed when reactions were carried out at room temperature (kinetic control), while N9-substituted analogs were produced at elevated temperatures (thermodynamic control). On the other hand, no differences in the stereochemical outcome of glycosylation were noticed for canonical purine nucleobases and their 8-aza analogues since ratios of α and β anomers appeared to be closely related to the structure of a sugar component. Multidirectional biological activities of 8-azapurines and their nucleosides, including antitumor, antiviral and antibacterial, were presented for the most acclaimed examples. However, none of these compounds was approved as a drug. The current interest in 8-azapurines and their nucleosides takes advantage of a significant fluorescence (opposite to purines), which was found to be a pH-dependent thus providing an excellent tool for advanced studies in nucleic acid chemistry.
Authors and Affiliations
Iwona E. Głowacka, Anna Zdzienicka
Keywords
Related Articles
- EP ID EP568469
- DOI -
- Views 123
- Downloads 0
Polimery z odciskiem molekularnym jako biomimetyki metaloenzymów
This paper presents methods of the synthesis and applications of biomimetic catalytic systems produced from molecularly imprinted polymers (MIP). MIPs contain cavities, which are complementary to the imprinted template,...
Immobilizowane alfa-amylazy i celulazy w zastosowaniach praktycznych
Today, more and more products made in biotechnological processes involving enzymes. The stability of the enzyme under process conditions are subjected to the immobilization on solid supports, which leads to a heterogeneo...
Glikozydy nasercowe : nowe trendy w chemii medycznej saponin i sapogenin
Plant secondary metabolites – ubiquitous low molecular weight chemicals which are not essentials for the host existence and reproduction but serve many auxiliary functions, are frequently occurring as glycosides, for whi...
Inżynieria komórkowa w systemach lab-on-a-chip
Lab-on-a-chip systems are promising tools in the field of cell engineering. Microfluidic systems are integrated microlaboratories consisting of many microstructures such as microchannels and microchambers, which can be u...
Betainy jako akceptory protonu
Ammonium alkanoates (ammonioalkanocarboxylates) are zwitterions (or inner salts, or betaines), because they possess formally charged ammonium and carboxylate groups separated by one or more sp3 carbon atoms. The chemistr...