Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes

• Published in: Organic communications Vol. 11; no. 1; pp. 23 - 34
• Main Authors: Fandaklı, Seda, Doğan, İnci Selin, Sellitepe, Hasan Erdinç, Yaşar, Ahmet, Yaylı, Nurettin
• Format: Journal Article
• Language: English
• Published: Gebze ACG Publications 01.01.2018
• Subjects: Acarbose; Data processing; Glucosidase; Hydroxylamine; Infrared radiation; Isomers; Mathematical analysis; NMR; Nuclear magnetic resonance; Oximes; Pyridines; Synthesis; α-Glucosidase
• ISSN: 1307-6175; 1307-6175
• DOI: 10.25135/acg.oc.38.18.02.067

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.