Synthesis, Theoretical Calculation and α-Glucosidase Inhibition of New Chalcone Oximes

 Seda Fandaklı, İnci Selin Doğan, Hasan Erdinç Sellitepe, Ahmet Yaşar and Nurettin Yaylı

Department of Chemistry, Faculty of Science, Karadeniz Technical University, 61080 Trabzon, Türkiye

Faculty of Pharmacy, Karadeniz Technical University, 61080 Trabzon, Türkiye

Abstract: A series of eleven hydroxy and methoxy substituted new chalcone oximes (2a-2k) were synthesized by the condensation of chalcone (1a-1k) with hydroxylamine hydrochloride in pyridine. Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H- 1H COSY, NOESY and ROESY), FT-IR, UV, LC-MS/MS spectral data and elemental analysis. These synthetic compounds (2a-k) were screened for their α-glucosidase inhibition. The most α-glucosidase inhibitory activity were observe on compounds 2a and 2b with in the range of 1.61-3.36 µM (IC 50 values) which were more active then acarbose (IC 50, 13,34 µM). IC 50 values of other synthesized compounds 2c-2h are within the range of 7,25-25,55 µM which were more or as active as acarbose, but, IC 50 values for compounds 2j-2k were not observed. The geometric isomers of compounds 2a-2k were calculated theoretically. Experimental and theoretical calculations showed that cisoid 1E,2E is the most stable geometrical isomer of all.

Keywords: Chalcone; chalcone oxime; α-glucosidase inhibition. © 2018 ACG Publications. All rights reserved.