Abstract
Glycosylation of 6-amino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine and its iodo- and bromo- analogues with the protected ribofuranose and 2′-deoxyribofuranose under different conditions resulted in the synthesis of N9- and N8-glycosylated purine nucleosides. Five key intermediate nucleosides, having 6-methoxy, 7-iodo, and 2-bromo groups, were further derivatized to 23 final 8-aza-7-deazapurine nucleoside derivatives. The structures of N9- and N8-glycosylated products were assigned based on UV and NMR spectra. HMBC analysis of 2D NMR spectra and X-ray crystallographic studies of the representative compounds unambiguously verified the connection of ribose ring to N9- or N8-position of the purine ring. The anticancer activity of these new compounds was evaluated.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Cited by
6 articles.
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1. Crystal structure determination and analyses of Hirshfeld surface, crystal voids, intermolecular interaction energies and energy frameworks of 1-benzyl-4-(methylsulfanyl)-3a,7a-dihydro-1H-pyrazolo[3,4-d]pyrimidine;Acta Crystallographica Section E Crystallographic Communications;2024-06-25
2. Crystal structure determination, Hirshfeld surface, crystal void, intermolecular interaction energy analyses, as well as DFT and energy framework calculations of 2-(4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid;Acta Crystallographica Section E Crystallographic Communications;2022-08-31
3. Synthesis and biological activity of aza and deaza analogues of purine nucleosides;Russian Chemical Reviews;2021-12-01
4. Isoguanine (2-Hydroxyadenine) and 2-Aminoadenine Nucleosides with an 8-Aza-7-deazapurine Skeleton: Synthesis, Functionalization with Fluorescent and Clickable Side Chains, and Impact of 7-Substituents on Physical Properties;The Journal of Organic Chemistry;2021-10-18
5. Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation;Journal of Agricultural and Food Chemistry;2021-09-15