Nucleosides 9: Design and synthesis of new 8-nitro and 8-amino xanthine nucleosides of expected biological activity

ABSTRACT

The coupling reaction of 1,3-dimethylxanthine (theophylline), 3-benzylxanthine and 3-benzyl-1-methylxanthine with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose afforded the corresponding protected nucleosides, respectively. Nitration of each of the theophylline and 3-benzy-1-methyllxanthine protected nucleosides yielded the corresponding 8-nitronucleosides derivatives, which were reduced to give the corresponding 8-aminonucleoside derivatives.

Debenzoylation of protected nucleosides formed by using methanolic sodium methoxide afforded the corresponding free N-nucleosides, respectively. The structures of products have been elucidated and reported and also some of the products were screened for their antimicrobial activity. Some of tested products showed moderate activity.

GRAPHICAL ABSTRACT

KEYWORDS:

• Synthesis
• nucleoside
• biological activity
• xanthine
• ribofuranose
• xanthine nucleoside

Funding

The authors thank King Abdulaziz City for Science and Technology (KACST), Kingdom of Saudi Arabia (KSA) for the financial support under project number AT36-076.