Abstract
We report here the synthesis of a series ofN-aryl-2,3-dihydrobenzo[1,4]dioxine-6-sulfonamideand itsN-substituted derivatives with benzyl chloride and ethyl iodide. Initially, 2,3-dihydrobenzo[1,4]dioxine-6-sulfonyl chloride (1) was subjected to react with various aryl amines(2a-e) to afford parent compoundsN-aryl-2,3-dihydrobenzo[1,4]dioxine-6-sulfonamide (3a-e). Atsecond step, these parent compounds were reacted with benzyl chloride (4) and ethyl iodide (5) asto synthesizeN-benzyl-N-aryl-2,3-dihydrobenzo[1,4]dioxine-6-sulfonamide (6a-e) andN-ethyl-N-aryl-2,3-dihydrobenzo[1,4]dioxine-6-sulfonamide (7a-e) in the presence of lithium hydride andN,Nꞌ-dimethylformamide respectively. FT-IR, Nuclear Magnetic Resonance (1H-NMR) and MassSpectrometry (MS) techniques were used to investigate the structures of these synthesizedcompounds. A fingerprinted study was conducted against some enzymes like butyrylcholin-esterase (BChE), acetylcholinesterase (AChE) and lipoxygenase (LOX). This study revealed thatmost of them demonstrated a moderate activity against butyrylcholinesterase (BChE) andacetylcholinesterase (AChE) however promisingly a good activity against lipoxygenase enzymewas observed. Finally, an antimicrobial and hemolytic activities of these sulfonamides wereprobed which confirmed that the parent sulfonamides 3b have the proficient antimicrobialactivities, while the derivatives 6a, 7a, 7b and 7cexplored a good activity against the selectedpanel of bacterial and fungal species. All the compounds were further computationally dockedagainst (LOX), (BChE) and (AChE) enzymes and these interaction highlighted the importance ofsulfonamides in the inhibition of the target enzymes.
M. Irshad, M. A. Abbasi, Aziz-ur-Rehman, M. Akram, Q. Ali, S. Z.Siddiqui, M. Shahid, M. Ashraf, M. A. Lodhi, S. B. Jamal. (2018) Pharmacological Evaluation and Synthesis ofNewSulfonamides Derivatives Based on 1,4-Benzodioxane, Pakistan Journal of Analytical & Environmental Chemistry, Volume 19, Issue 2 .
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