Synthesis of novel 1,2,3-triazole based acridine and benzothiazole scaffold N-glycosides with anti-proliferative activity, docking studies, and comparative computational studies

Abstract In this investigation, the cycloaddition reaction of azide-alkyne derivatives 1a,b with glucopyranose azide 2a,b was catalyzed via Cu(I) to afford the corresponding acetylated 1,2,3-triazole N-glycoside derivatives 3a and 3b; respectively. The observed 1,2,3-triazole N-glycoside derivatives were examined via spectral analysis such as FT-IR,1HNMR, and mass spectrum. The investigated N-glycoside derivatives were exhibited antitumor activity against HCT-116, A549, HepG2, and MCF-7 tumor cells. The N-glycoside derivatives were docked against PDBID:5h38 and PDBID:4hdq with energy affinity rang (-8.87,-7.65kcal/mol) and bond distance 2.69A-2.91A and attached with several hydrogen-bonding interactions inside the pocket of protein which confirmed the higher activity of benzo[d]thiazole and acridine rings attached with 1,2,3-triazole N-glycoside moiety. Furthermore, the theoretical studies of 1,2,3-triazole N-glycosides 3a and 3b utilized DFT/B3LYP/6-31G(d) basis set were investigated through bond length A, and bond angle degrees, dihedral angle, geometrical parameters, FMO, surface contour which confirmed the stability of benzothiazole and acridine rinds in their energies and physical parameters.