Synthesis and cytotoxic activity of 4,6-diaminopyrazolo[3,4-d] pyrimidine riboside and its 3-carbamoyl derivative

Garaeva, L. D.; Korbukh, I. A.; Dobrynin, Ya. V.; Nikolaeva, T. G.; Preobrazhenskaya, M. N.

doi:10.1007/bf00763519

Cited by 1 publication

(1 citation statement)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A classical example of these biologically active analogues is allopurinol, which is an approved drug for the treatment of gout and it is also active against several Leishmania and trypanosome species [ 3 ]. 8-Aza-7-deazapurine-2,6-diamine and its riboside 5 are powerful purine nucleoside antagonists [ 4 ] ( Figure 1 ), and 2′-deoxy-2′-β-fluoro-8-aza-7-deazapurine nucleosides display significant activity against HBV [ 5 ]. 8-Aza-7-deazapurines closely resemble the structure of purine with only C8 and N7 exchanged, which make their nucleosides excellent substrates of bio-enzymes [ 6 , 7 ] and ideal mimics of the canonical purine constituents of DNA or RNA.…”

Section: Introductionmentioning

confidence: 99%

Investigation of 8-Aza-7-Deaza Purine Nucleoside Derivatives

Ren

An²,

Tao

2019

Molecules

View full text Add to dashboard Cite

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.

show abstract