An efficient ultrasonic synthetic approach, DFT study, and molecular docking of 6a-hydroxy-9-nitro-6,6a-dihydro-isoindolo[2,1-a] quinazoline-5,11-dione derivatives as algaecides for refining wastewater

摘要

In the present work, reaction of 3-nitrophthalic anhydride with anthranilic acid to afford the corresponding anthranil that is treated with acetic anhydride that yielded the 2-benzoxazinonyl-5-nitrobenzoic acid (BNBA) could be isomerized to the stereogenic 9-nitrobenzoxazinone[2,3-a]isoindolinone acetate (NBIA) via basic reaction conditions. A reaction of the BNBA -> NBIA was allowed with series of nitrogen nucleophiles such as formamide and hydrazine derivatives, for example, hydrazine hydrate, hydroxyl amine, acetic hydrazide, thiosemicarbazide, thiocarboihydrazide, and some amino acid, for example, glycine, alanine, and some aliphatic amine, for example, octyl amine, decyl amine, and aromatic amine, for example, aniline, o-toluidine, 4-aminobenzoic acid, and carbon nucleophiles such as malononitrile and diethylmalonate. The basicity of previous nucleophiles and thermal stability of the products can be controlled on the course of reaction. The chemical structure of the synthesized compounds can be confirmed by micro-analytical, spectral data, and they are optimized by quantum chemical parameters (DFT study) to identify the thermal stability of the products. The data obtained from the molecular modeling were correlated with those obtained from the biological screening. A novel sequence of quinazoline derivatives were synthesized, evaluated for their algaecides activity against compounds 1, 2b, and 6 that showed the highest algaecides activities of this series with relatively low toxicity in the median lethal dose test. The obtained results proved that the most active compounds could be useful models for future design, adaptation, and investigation to construct more active analogs.