Preparation and characterization of five membered heterocyclic derivatives from chalcone and evaluation of their biological activity as antioxidant and physical property
Abstract
Five-membered heterocycles were prepared in two steps. In the first step, 2-acetylnaphthalene was condensed with 4-(2-pyridyl)benzaldehyde or with biphenyl-4-carboxaldehyde in basic ethanol to give chalcones (A) and (B). In the second step, each chalcone reacted with hydroxylamine hydrochloride, phenylhydrazine, 2,4-dinitrophenylhydrazine or hydrazine. This gave two isoxazolines (1, 5) and six pyrazolines (2, 3, 4, 6, 7, 8). The ring closures were run in ethanol at 40 °C for 22–26 h. FT-IR, 1H-NMR and 13C-NMR spectra were used to assign the structures. For all ten compounds, the colour, melting point, Rf value and molecular weight were recorded. Melting points ranged from 213–215 °C for compound (A) to 288–290 °C for compound (7). The biological activity of compounds (3), (4), (5) and (6), which have a strong inhibitory effect, was then studied with the DPPH radical scavenging assay. Five concentrations from 500 to 2500 µg/mL were tested, with ascorbic acid as the reference. Compound (5) gave the highest scavenging value, 93.1 % at 2500 µg/mL. Compound (6) gave the lowest, 38.9 % at 500 µg/mL.
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