تحضير ودراسة الفعالية الحيوية والتراكيب لمشتقات ١، ٢، ٣، ترايازول المستند على D- كالكتوز

Synthesis, biological activity and structural study of D- galactose- based 1,2,3- Triazole Derivatives

This study included synthesis of new galactose based 1,2,3-triazoles containing fluorobenzyl moiety and monitor the toxicity profile against the MSC. At the beginning, 2-fluor-, 3-fluoro and 4-fluorobenzyl azides 68a−c were prepared by the reaction of corresponding benzyl bromides 68a−c with sodium azide in DMSO at fifty degrees for 24h to obtain the mentioned azido compounds in very good to excellent yield 81−92%. In a parallel step, zinc chloride and sulfuric acid were used to catalyze the reaction of D-galactose (69) with access of acetone at ambient temperature for 6h to obtain the α-D-galactose diacetonide (70) in very good yield 81%. This derivative was reacted with propargyl bromide in DMF at 0 °C−r.t. to produce Alkynyl-α-D-galactosyl derivative 71 in 88% yield. Moreover, the conformation of derivative 71 was determined using computational study and 2D NMR technique. In addition , 1,2,3-triazole derivatives 72a−c were synthesized through the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). Alkyne 71 was reacted with azides 68a−c in the aid of Na ascorbate and CuSO4.5H2O in DMSO at 50 °C for 36h to get the targeted 1,2,3-triazole derivatives 72a−c in 83−90% yield. The synthesized compounds have been characterized through NMR(nuclear magnetic resonance), FTIR(Fourier-transform infrared), HSQC(heteronuclear single quantum coherence), COSY(correlated spectroscopy), HMBC(heteronuclear multiple bond correlation), and HRMS(high-resolution mass spectrometry). Compounds 72a−c had been studied towards human being mesenchymal stem cells and it discovered that these derivatives hold fair cytotoxicity.