Acetamide Derivatives of N-Methyl Hydroxyaniliniumsulfate: Design, Synthesis, Spectral Characterization and in silico Study to Report them as Therapeutic Agents

Various biological activities have been found to demonstrate the compounds bearing sulfamoyl and acetamoyl groups. A series of O- and N-substituted derivatives, beginning with planetol (1), were synthesised in the present research work. Aq was used to treat the first N-methyl-4-hydroxyanilinium sulphate (1; planetol or metol) with various aryl sulfonyl chlorides (2a-j). Solution of sodium carbonate as a reaction medium to produce N-substituted derivatives, 3a-j. The electrophile, N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-bromoacetamide (5), was prepared in a weak basic aqueous medium by the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (4) and 2-bromoacetylbromide. By gearing up the electrophile, the target O-substituted molecules, 6a-j, were synthesised, 5 with the molecules, 3a-j, using LiH as the activator in a polar aprotic solvent. The suggested structures of all the molecules synthesised were confirmed by IR, 1H-NMR and spectral data from EIMS. The synthesised molecules were made as better cholinesterase inhibitors and marginally better antibacterial agents by in vitro enzyme inhibition and antibacterial studies. To explore the binding modes of the synthesized compounds, all of them were computationally docked against the active sites of acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase (LOX). The compounds displayed important interactions with the experimental data and a strong correlation.

Author (s) Details

Dr. Misbah Irshad
Department of Chemistry, Division of Science and Technology, University of Education, Township Campus, Lahore-54770, Pakistan and Department of Chemistry, Government College University, Lahore-54000,

Prof. Dr. Muhammad Athar Abbasi
Department of Chemistry, Government College University, Lahore-54000, Pakistan.

Aziz- Ur-Rehman
Department of Chemistry, Government College University, Lahore-54000, Pakistan.

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