Synthesis and NMR Spectroscopic Characteristics of a Series of Hydrazide‐Hydrazones Containing Furoxan Ring Derived from Isoeugenoxyacetic Acid

Abstract

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 13C‐NMR spectra of the examined hydrazide‐hydrazones are caused by EN–C(O) and ZN–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 IC50 = 47, 68, 79, and 103 μg/mL.