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Synthesis and NMR Spectroscopic Characteristics of a Series of Hydrazide‐Hydrazones Containing Furoxan Ring Derived from Isoeugenoxyacetic Acid
Author(s) -
Dinh Nguyen Huu,
Tuyet Lan Hoang Thi,
Thu Trang Tran Thi,
Van Hoan Pham
Publication year - 2012
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.868
Subject(s) - hydrazide , chemistry , furoxan , ring (chemistry) , isonicotinic acid , proton nmr , nuclear magnetic resonance spectroscopy , stereochemistry , carbon 13 nmr , organic chemistry , nitric oxide
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 1 H‐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 1 H‐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.