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Molecules 2019, 24(5), 983; https://doi.org/10.3390/molecules24050983

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

1,2
,
2,*
and
1,*
1
College of Chemistry and Molecular Engineering, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, China
2
Zhengzhou Granlen PharmaTech, Ltd., 1300 Eastern Hanghai Road, Zhengzhou 450016, China
*
Authors to whom correspondence should be addressed.
Received: 22 February 2019 / Accepted: 5 March 2019 / Published: 11 March 2019
(This article belongs to the Section Organic Chemistry)
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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. View Full-Text
Keywords: glycosylation; 8-aza-7-deazapurine; nucleoside; pyrazolo[3,4-d]pyrimidine; 2D NMR; crystallographic analysis glycosylation; 8-aza-7-deazapurine; nucleoside; pyrazolo[3,4-d]pyrimidine; 2D NMR; crystallographic analysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ren, H.; An, H.; Tao, J. Investigation of 8-Aza-7-Deaza Purine Nucleoside Derivatives. Molecules 2019, 24, 983.

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