Paper
Synthesis, Spectral Analysis and Biological Evaluation of 5-Substituted 1,3,4-Oxadiazole-2-yl-4-(Piperidin-1-ylsulfonyl)Benzyl Sulfide
Published Jul 18, 2016 · H. Khalid, Aziz‐ur‐Rehman, M. Abbasi
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Abstract
1,3,4-Oxadiazole bearing compounds are one of the most attractive class for researchers due to their biological activities. In the undertaken research, a new series of 5-substituted 1,3,4-oxadiazole-2-yl-4-(piperidin-1-ylsulfonyl)benzylsulfides (6a–k) were synthesized. The synthesis was carried out by converting different organic acids sequentially into corresponding esters, hydrazides and 5-substituted-1,3,4-oxadiazole-2-thiols (4a–k). Finally, the target compounds, 6a–k were prepared by stirring 5-substituted-1,3,4-oxadiazole-2-thiols with 1-(4-(bromomethyl)phenyl sulfonyl)piperidine (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride. All the structures were elucidated by modern spectroscopic techniques. The synthesized compounds were screened against butyrylcholinesterase (BChE) enzyme and also subjected for molecular docking studies to find ligand-BChE binding affinity and ligand orientation in active sites of human BChE protein. Amino acid residues such as Gly116, His438, Tyr332 and Ser198 are found to be important common residues for binding of highlighted compounds and are likely to be involved in the ligands’ stabilization in the binding site.
5-Substituted 1,3,4-oxadiazole-2-yl-4-(piperidin-1-ylsulfonyl)benzylsulfides show potential as inhibitors of butyrylcholinesterase enzyme, with common residues Gly116, His438, Tyr
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