Abstract
Condensation products of 5-substituted phenyl-2-furoyl hydrazide with different monosaccharides d-glucose, d-galactose,d-mannose, d-fucose and d-arabinose were prepared. The anomerization and cyclic-acyclic isomers were investigated by 1H NMR spectroscopy. The results showed that, except for the d-glucose derivatives, which were in the presence of β-anomeric forms, all derivatives were in an acyclic Schiff base form. Their antifungal and antitumor activities were studied. The bioassay results indicated that some title compounds showed superior effects over the commercial positive controls.
Highlights
Carbohydrates participate in various vital processes, showing important physiological and biological activities
It could be deduced that the skeleton of 5-phenyl-2-furoyl hydrazide displayed important antitumor activity, which was in agreement with our former results [20–24,26,27]
Infrared Spectroscopy (IR) spectra were recorded on a NEXUS-470 FTIR (Nicolet) spectrometer with KBr pellets. 1H Nuclear Magnetic Resonance (NMR) spectra were recorded with Bruker DPX300 (Bruker, Billerica, MA, USA) and JEOL JNM-ECA500 instrument (JEOL Ltd., Tokyo, Japan), while tetramethylsilane was used as the internal standards
Summary
Carbohydrates participate in various vital processes, showing important physiological and biological activities. Researchers synthesized isoniazid- hydrazones derivatives that were reported to have inhibitory activity in mice infected with various strains of M. tuberculosis and showed less toxicity in these mice than isoniazid [18] because of the blockage of –NH2 group. These findings further support the growing importance of the synthesis of hydrazide-hydrazones compounds [19]. In continuation of our research on the synthesis of biological heterocyclic compounds, a series of novel glycosyl hydrazide derivatives containing 5-phenyl-2-furan moiety were designed and synthesized (Scheme 1).
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