Synthesis, Spectroscopy, and α-Glucosidase Inhibitory Activity of 3-Substituted Hydrazone Derivatives and Crystal Structure of (1E,2E)-1,2-Bis[1-(3-methoxyphenyl)ethylidene]hydrazone

Abstract

Six 3-substituted hydrazone derivatives [R = −OCH₃ (1), −NH₂ (2), −NO₂ (3), −F (4), −Cl (5), and −Br (6)] were synthesized by condensation reaction. Their structures were elucidated by ¹H NMR, FT-IR and UV-Vis spectroscopy. The synthesized compounds were further evaluated for their α-glucosidase inhibitory activity. Strong activity was found for 1 and 3. The crystal structure of 1 was determined by single crystal X-ray diffraction: a = 6.9743(1) Å, b = 18.3627(3) Å, c = 12.0207(2) Å, β = 96.087(1)o, sp. gr. P2₁/c, Z = 4. The molecule of 1 is twisted with the dihedral angle between the two phenyl rings being 51.91(4)°. In the crystal packing, the molecules are linked into chains by C–H···π interactions.