Synthesis and Characterization of Some New Nucleoside Analogues from Substituted Benzimidazole and Evaluation of Their Biological Activities

Abstract

This research includes the synthesis of some new nucleoside analogues via 1,3-
dipolar cycloadditon reaction starting with 1,3,4,6- Tetra- O-benzoyl –2 – azido-2-
deoxy- β – D- fructofuranose (F3) which was prepared in three steps ,protection
(benzoylation ) , bromination and azotation ((F1-F3) from D- fructose as sugar
moiety while the base moiety , 2-substituted benzimidaole derivatives (A1-A5)
were synthesized by condensation of O-phenylenediamine with different aromatic
aldehyde .
Nucleophilic substitution of propargyl bromide with benzimidaole derivatives (gave
the N- substituted compounds (B1-B5) which were reacted with azido sugar through
1,3- dipolar cycloadditon reaction to give nucleoside analogues (C1-C5) .
Debloking of these nucleoside using sodium methoxide in methanol afforded our
target the free nucleoside analogues (D1-D5).
All prepared compound were identified by FT-IR and some of them with 1H-NMR
and 13C-NMR. The synthesized compounds (D1-D5) were screened for their in-vitro
antibacterial and antifungal activity.