Synthesis and characterization of some new nucleoside analogues from substituted benzimidazole and evaluation of their biological activities

Abstract EN

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.