Synthesis, Antioxidant, and Antimicrobial Activities of Novel Bis-Aroylbenzofuran Fused 1,2,3-Triazoles Bearing Alkane Spacers

Abstract

A series of novel fused bis-aroylbenzodifuran derivatives linked via bis-1,2,3-triazole moiety containing alkane spacers 15, 19a–19d are synthesized in 68–80% yields by the Huisgen cycloaddition (Click) reaction of alkane azides 4–8 with acetylene intermediate 3 followed by cyclization of the corresponding bishydroxyacetophenone derivatives 9–13 with various p-substituted phenacyl bromides 14a–14d. The isolated compounds are characterized by IR, NMR and mass spectral data. The title compounds are screened in vitro for their antimicrobial and antioxidant activities. The results of the studies indicate antimicrobial activity of compounds 16a and 16b compared to that of the standard Streptomycin. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity test of the synthesized compounds indicates the compounds 15d and 16d as highly active as compared to the standard 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT).