Nukleozydy 8-azapurynowe : synteza i aktywność biologiczna

Głowacka, I. E.; Zdzienicka, A.

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Tytuł artykułu

Nukleozydy 8-azapurynowe : synteza i aktywność biologiczna

Autorzy

Głowacka I. E. , Zdzienicka A.

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Warianty tytułu

Nucleosides of 8-azapurines : synthesis and the biological activity

Języki publikacji

Abstrakty

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.

Słowa kluczowe

analogi nukleozydów 8-azanukleozydy 8-azapuryny aktywność biologiczna

nucleoside analogues 8-azanucleosides 8-azapurines biological activity

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2017

Tom

[Z] 71, 3-4

Strony

147--174

Opis fizyczny

Bibliogr. 49 poz., schem.

Twórcy

autor

Głowacka I. E.

iwona.glowacka@umed.lodz.pl

Zakład Chemii Bioorganicznej, Wydział Farmaceutyczny, Uniwersytet Medyczny w Łodzi, ul. Muszyńskiego 1, 90-151 Łódź

autor

Zdzienicka A.

Zakład Chemii Bioorganicznej, Wydział Farmaceutyczny, Uniwersytet Medyczny w Łodzi, ul. Muszyńskiego 1, 90-151 Łódź

Bibliografia

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Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-37c696a3-06f6-456b-95ae-9c8f3e487a56