Synthesis and Biological Assessment of New Nucleosides of Pyrido[2,3-d]pyrimidine Derivatives Bearing Ribose and 2-Deoxyribose Moieties

Abstract

Herein, it is unprecedentedly reported the synthesis of some new β-D-ribo and β-D-2-dexoyribofuranosyl nucleosides of pyrido[2,3-d]pyrimidines derivatives where the sugar moiety is linked to pyrido[2,3-d]pyrimidines via S or N glycosidic bond. Therefore, pyrido[2,3-d]pyrimidine derivatives 3 and 6 were utilized as scaffolds to be incorporated with ribose and 2-deoxyribose moieties. The glycosylation reactions were carried out under optimized conditions to enhance the regioselectivity and stereoselectivity during the glycosylation coupling. Various strategies have been applied to afford the desired N-nucleosides 16 and 19. Other approaches were utilized to afford the S-nucleosides 9, 13, 21, and 24. The structural elucidations of the novel nucleosides formed are reported and ascertained by using IR, ¹H NMR, ¹³C NMR spectra and microanalysis. All the synthesized compounds were screened against a panel of microorganism strains for antibacterial and antifungal activities as well as antitumor evaluation.

Keywords:

• Pyrido[2,3-d]pyrimidne
• thione
• β-configuration
• S- and N-glycosylation
• nucleosides
• potency

Acknowledgments

Financial support from the Science and Technology Development Fund of Egypt (STDF) is gratefully acknowledged.

Disclosure statement

No potential conflict of interest was reported by the authors.