Synthesis and NMR spectroscopic characteristics of a series of hydrazide-hydrazones containing furoxan ring derived from isoeugenoxyacetic acid

摘要

A novel hydrazide, 2-methoxy-4-(3-methyfuroxan-4-yl)-5- nitrophenoxyacetylhydrazine, was prepared from isoeugenoxyacetic acid. The hydrazide was condensed with aromatic aldehydes to give a series of 20 hydrazide-hydrazones incorporating the furoxan ring. The structure of obtained compounds was determined by analytical and spectral data. It was demonstrated that the two sets of resonance signals in the ~1H-NMR and ~(13)C-NMR spectra of the examined hydrazide-hydrazones are caused by E _(N-C(O)) and Z _(N-C(O)) conformers. The energy barriers for the conformation exchange were determined by ~1H-NMR-measurement at various temperatures. Among seven tested hydrazide-hydrazones, four compounds exhibit inhibition activities in vitro on human epidermis carcinoma (KB-cell) with IC _(50) = 47, 68, 79, and 103 μg/mL.