4-Fluoro-N'-(2-hydroxy-3-methoxybenzylidene) benzohydrazide and its Oxidovanadium(V) Complex: Syntheses, Crystal Structures and Insulin-enhancing Activity

Acta Chim Slov. 2016;63(3):670-7. doi: 10.17344/acsi.2016.2589.

Abstract

A hydrated hydrazone compound, 4-fluoro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate (H2L · H2O), was prepared and characterized by elemental analysis, HRMS, IR, UV-Vis and 1H NMR spectroscopy. Reaction of H2L, kojic acid (5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one; Hka) and VO(acac)2 in methanol afforded a novel oxidovanadium(V) complex, [VO(ka)L]. The complex was characterized by elemental analysis, IR, UV-Vis and 1H NMR spectroscopy. Thermal analysis was also performed. Structures of H2L and the complex were further confirmed by single crystal structural X-ray diffraction. The vanadium complex is the first structurally characterized vanadium complex of kojic acid. Insulin-mimetic tests on C2C12 muscle cells indicate that the complex significantly stimulated cell glucose utilization with cytotoxicity at 0.11 g L-1.

MeSH terms

  • Animals
  • Cell Line
  • Crystallography, X-Ray
  • Glucose / metabolism
  • Hydrazones / chemistry*
  • Insulin / biosynthesis*
  • Mice
  • Molecular Structure
  • Muscle, Skeletal / cytology
  • Muscle, Skeletal / metabolism
  • Vanadium Compounds / chemistry*

Substances

  • Hydrazones
  • Insulin
  • Vanadium Compounds
  • Glucose