Synthesis, characterization and biological activities of 3-nitro isoindoline-1,3-dione analogues

Abstract

N-substituted phthalimides are biologically active chemicals with a broad range of applications. In this present research work, eight 3-Nitroisoindoline-1,3-dione analogues were synthesized and characterized. Furthermore, their antibacterial, antifungal and antioxidant activities were evaluated in vitro. Synthesized compounds were purified using the recrystallization process and the purity was confirmed by thin-layer chromatography. The structures were characterized by FTIR and mass spectroscopic analysis. Using the Disc diffusion method, synthetic 3-Nitroisoindoline-1,3-dione analogues were tested for antibacterial activity against Bacillus spp and Escherichia coli, as well as antifungal activity against Aspergillus spp and Trichoderma spp. Based on the results that compound 2- (CF3 and Cl groups at the 3rd and 4th positions respectively), 3,4-(OCH3 group attached to the 4th position), 7- (CH3 group attached to the 2nd and 3rd position), and showed inhibitory effects against Bacillus spp with the zone of inhibition ranging from 6.66 – 9.83 mm. The compounds 1- (Cl group attached to the 2nd position), 2, and 8- (CF3 group attached to the 4th position) showed inhibitory effects against Escherichia coli with ZOI ranging from 7.83 – 10.66 mm. The compounds 1,3, and 5-(Br group attached to the 4th position) showed inhibitory effects against Aspergillus spp with ZOI ranging from 6.5 – 6.83 mm. The compounds 2, 6- (Cl the group attached to the 4th position), and 8 showed an inhibitory effect against Trichoderma spp with ZOI ranging from 7.5 – 8.0 mm. Synthesized 3-nitro isoindoline1, 3-dione was tested for antioxidant activity by using the DPPH assay. Compound 2 showed moderate antioxidant activity. These 3-nitroisoindoline-1,3- dione analogues could be synthesized and used as antibacterial and antifungal and antioxidant agents.