تحضير و دراسة الفعالية الحيوية لمشتقات ثنائي 3,2,1-ترايازول بدءا من سكر المانتول

Synthesis and Biological Activity of Bis-1,2,3-Triazole Derivatives Starting from D-Mannitol

Abstract

The current work is including synthesis of new mannitol based bis-1,2,3-triazoles and study of their cytotoxicity. First, aromatic azides 99a‒c were synthesized in excellent yields via the reaction of corresponding benzyl bromides with sodium azide in DMSO. In a separate step, the commercially available D-mannitol was reacted with acetone in the presence of zinc chloride to give 1,2:5,6-di-O-isopropylidene-D-mannitol (101) in 54% yield, which was treated with propargyl bromide in DMF to produce 3,4-bis-O-propargyl-1,2:5,6-di-O-isopropylidene-D-mannitol (102) in a very good yield. The copper catalyzed cycloaddition reaction of the dialkyne 102 with azides 99a‒c gave the bis-1,2,3-triazole derivatives 103 a‒c in nearly very good yields. The final step in the synthesis was the acetal groups’ removal of compounds 103 a‒c to afford the deprotected triazole derivatives 104 a‒c in quantitative yields. The synthesized compounds were characterized followed by TLC, FT-IR, NMR, COSY, HSQC, HMBC and HRMS. Compounds 103 a‒c were in vitro screened against human mesenchymal stem cells and found to possess fair cytotoxicity.