Three chiral pyrazoline derivatives were synthesized by a flavanone ring‐opening reaction followed by cyclocondensation with hydrazine hydrate to give better yields. Their enantiomeric resolution was achieved using polysaccharide chiral stationary phase columns consisting of cellulose (Chiralcel®OD‐RH, Chiralcel®OZ‐3) and amylose (Chiralpak®IA) by high‐performance liquid chromatography. The separation was affected by the nature and concentration of the alcohol modifiers in the mobile phase. Taking 5‐methoxy‐2‐(3‐phenyl‐4,5‐dihydro‐1H‐pyrazol‐5‐yl)phenol (3a) as an example, the best separation was obtained by using the Chiralpak®IA column, with a separation factor α = 1.24 and Rs = 5.66 within an analysis time of <30 min. The diarylpyrazolines showed good antioxidant activity, studied by the DPPH method.
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