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Potent acetylcholinesterase inhibitors: Synthesis, biological assay and docking study of nitro acridone derivatives

2016; Elsevier BV; Volume: 161; Linguagem: Inglês

10.1016/j.jphotobiol.2016.05.028

1873-2682

Mehtab Parveen, Afroz Aslam, Shahab A.A. Nami, Ali Mohammed Malla, Mahboob Alam, Dong‐Ung Lee, Sumbul Rehman, Pedro Silva, Manuela Ramos Silva,

Cholinesterase and Neurodegenerative Diseases

The reaction of o-halobenzoic acid with aniline derivatives and their subsequent cyclization reaction yielded the acridone derivatives. The series of nitro acridone derivatives were prepared by Ullmann condensation in presence of copper as catalyst and were characterized by FTIR, 1H, 13C NMR and mass spectra. The structure of 5-nitro-(2-phenyl amino) benzoic acid (4) was confirmed by X-ray crystallography and was found to crystallize in P21/c space group. The in vitro efficacy of the compounds for their acetylcholinesterase (AChE) and antimicrobial inhibitory activities have been evaluated against the standard drugs Ampicillin and Gentamicin against Gram positive and Gram negative bacteria. 1,7-Dinitroacridone was found to be the most potent AChE inhibitor (IC50 = 0.22 μM). Moreover, the compounds have been screened for their antioxidant activity using the DPPH assay. Also, docking study results were found to be in good agreement with the results obtained through in vitro experiments. The docking study further predicted possible binding conformation.