New chalcone-3-O-glycoside derivatives: Synthesis and characterization

Abstract

Seven novel carbohydrate conjugates of new chalcone-3- O-glycosides were synthesized and characterized. Starting from the substituted 3′-hydroxyarylmethylacetophenone derivatives (chalcones) with α-acetobromoglucose in anhydrous acetone were synthesized 2,3,4,6-tetra- O-acetyl-3′- O-β-d-glucopyranosyloxychalcones. Deblocking the latter with CH3ONa in dry methanol results in substituted chalcone-3- O-glycosides (3′- O-β-d-glucopyranosyloxychalcones). The structures of the newly synthesized chalcone-3- O-glycosides were characterized based on 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, mass spectroscopy, and Fourier-transform infrared spectroscopy.

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

“…The general synthesis route of chalcones (3a-3f) and 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives (4a-4f) are given in Table 1 and Figure 2. Firstly, the chalcones were synthesized by Claisen-Schmidt condensation among the aromatic aldehydes and the substituted acetophenone utilizing reported methods in the literature (Abdel-Halim et al, 2020;Çelik, 2020). Secondly, for compounds 4a-4f, chalcones have been converted into pyrazoline molecules by intramolecular Michael addition with hydrazine hydrate in refluxing ethanol and acetic acid as a catalyst (Table 1 and Figure 2) (Li et al, 2017;Çelik et al, 2020;Dofe et al, 2020;Farooq and Ngaini, 2020).…”