Facile synthesis of N-aroylurea analogs as potential antioxidants

Abstract

N,N'-Dicyclohexylcarbodiimide (DCC) is a widely used dehydrating and oxidizing agents for the synthesis such as proteins, amides and esters. The study reports synthetic application of the DCC to form N-aroylurea analogs and their antioxidant activity. Results showed that N-benzoyl-N,N'-dicyclohexylurea (Ia), N,N'-dicyclohexyl-N-3,5-dinitrobenzoylurea (Ib) and N,N'-dicyclohexyl-N-[(E)-3-phenylacryloyl]urea (Ic) were readily accomplished by facile one pot reaction of DCC with benzoic or cinnamic acid in the presence of triethylamine. The reaction took place via rearrangement of O-aroylurea intermediate to furnish relatively good yields of the analogs Ia-c. In addition, at 200 μg/mL, the urea analog Ic starts to mimic superoxide scavenging activity. © EuroJournals Publishing, Inc. 2009.