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

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 N?- and N?-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 N?- and N?-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 N?- or N?-position of the purine ring. The anticancer activity of these new compounds was evaluated.

SUBMITTER: Ren H 

PROVIDER: S-EPMC6429420 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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

Ren Hang H   An Haoyun H   Tao Jingchao J  

Molecules (Basel, Switzerland) 20190311 5

Glycosylation of 6-amino-4-methoxy-1H-pyrazolo[3,4-<i>d</i>]pyrimidine and its iodo- and bromo- analogues with the protected ribofuranose and 2'-deoxyribofuranose under different conditions resulted in the synthesis of <i>N</i>⁸- and <i>N</i>⁸-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 <i>N</i>⁸- and <i>N</i>⁸-glycosylated produ  ...[more]

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