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Synthesis, Biological Evaluation and Docking Study of Mono- and Di-Sulfonamide Derivatives as Antioxidant Agents and Acetylcholinesterase Inhibitors. 2022

Seyit Ali Güngör, and İrfan Şahin, and Özge Güngör, and Tugba Taskin Tok, and Muhammet Köse
Chemistry Department, Kahramanmaras Sütcü Imam University, 46100, Kahramanmaras, Turkey.

Mono(M1-M5)- and di(DM1-DM5)-sulfonamide derivatives were synthesized by the reaction of 4-iodobenzenesulfonyl chloride compound and aniline derivatives in basic medium. The structures of sulfonamide derivatives were characterized by spectroscopic and X-ray diffraction methods. All compounds were screened for acetylcholinesterase (AChE) inhibitory studies and 2,2-diphenyl-1-picrylhydrazil (DPPH) radical scavenging activities. Among the compounds tested, compound M1 showed the best activity against both AChE (IC50 =42.09 μg/mL for AChE) and DPPH (IC50 =9.94 μg/mL for DPPH). By placing compounds at the active site of AChE, their binding energies and modes were determined. Docking studies were performed in order to investigate binding interaction between the synthesized compounds and AChE. The most active M1 compound showed its low CDOCKER energy (-65,834 kcal/mol).

UI MeSH Term Description Entries
D002712 Chlorides Inorganic compounds derived from hydrochloric acid that contain the Cl- ion. Chloride,Chloride Ion Level,Ion Level, Chloride,Level, Chloride Ion
D002800 Cholinesterase Inhibitors Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. Acetylcholinesterase Inhibitor,Acetylcholinesterase Inhibitors,Anti-Cholinesterase,Anticholinesterase,Anticholinesterase Agent,Anticholinesterase Agents,Anticholinesterase Drug,Cholinesterase Inhibitor,Anti-Cholinesterases,Anticholinesterase Drugs,Anticholinesterases,Cholinesterase Inhibitors, Irreversible,Cholinesterase Inhibitors, Reversible,Agent, Anticholinesterase,Agents, Anticholinesterase,Anti Cholinesterase,Anti Cholinesterases,Drug, Anticholinesterase,Drugs, Anticholinesterase,Inhibitor, Acetylcholinesterase,Inhibitor, Cholinesterase,Inhibitors, Acetylcholinesterase,Inhibitors, Cholinesterase,Inhibitors, Irreversible Cholinesterase,Inhibitors, Reversible Cholinesterase,Irreversible Cholinesterase Inhibitors,Reversible Cholinesterase Inhibitors
D000077145 Sulfanilamide A short-acting sulfonamide used as an anti-infective agent. It has lower anti-bacterial activity than SULFAMETHOXAZOLE. 4-aminobenzenesulfonamide,Azol Polvo,Sulfanilamide Barium Salt,Sulfanilamide Cadmium Salt,Sulfanilamide Hydrochloride,Sulfanilamide Lithium Salt,Sulfanilamide Magnesium Salt,Sulfanilamide Monohydrate,Sulfanilamide Silver Salt,Sulfanilamide Sodium,Sulfanilamide Sodium Salt,Sulfanilamide Strontium Salt,Sulfanilamide Zinc Salt,Sulphanilamide,4 aminobenzenesulfonamide
D000110 Acetylcholinesterase An enzyme that catalyzes the hydrolysis of ACETYLCHOLINE to CHOLINE and acetate. In the CNS, this enzyme plays a role in the function of peripheral neuromuscular junctions. EC 3.1.1.7. Acetylcholine Hydrolase,Acetylthiocholinesterase,Hydrolase, Acetylcholine
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D062105 Molecular Docking Simulation A computer simulation technique that is used to model the interaction between two molecules. Typically the docking simulation measures the interactions of a small molecule or ligand with a part of a larger molecule such as a protein. Molecular Docking,Molecular Docking Simulations,Molecular Docking Analysis,Analysis, Molecular Docking,Docking Analysis, Molecular,Docking Simulation, Molecular,Docking, Molecular,Molecular Docking Analyses,Molecular Dockings,Simulation, Molecular Docking

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