Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Abbasi, Muhammad Athar; Islam, M.I.; Rehman, Azizur; Rasool, Shahid; Rubab, Kaniz; Hussain, Ghulam; Ahmad, Irshad; Ashraf, Muhammad; Shahid, Muhammad; Shah, Syed Adnan Alı

doi:10.4314/tjpr.v15i3.22

Cited by 6 publications

(3 citation statements)

References 17 publications

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“…The hemolytic activity of the compound was studied as per the reported method. , Freshly obtained heparinized bovine blood (3 mL) was collected from the Department of Clinical Medicine and Surgery, University of Agriculture, Faisalabad, Pakistan. Blood was centrifuged for 5 min at 1000 g , plasma was discarded, and cells were washed three times with 5 mL of chilled (4 °C) sterile isotonic phosphate-buffered saline (PBS) at pH 7.4.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity

et al. 2023

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The aim of this work was to bring forth some new hybrid molecules having pharmacologically potent indole and 1,3,4-oxadiazole heterocyclic moieties unified with a propanamide entity. The synthetic methodology was initiated by esterification of 2-(1H-indol-3-yl)acetic acid (1) in a catalytic amount of sulfuric acid and ethanol in excess, to form ethyl 2-(1H-indol-3-yl)acetate (2), which was converted to 2-(1H-indol-3-yl)acetohydrazide (3) and further transformed to 5-(1H-indole-3-yl-methyl)-1,3,4oxadiazole-2-thiol (4). 3-Bromopropanoyl chloride (5) was reacted with various amines (6a−s) in aqueous alkaline medium to generate a series of electrophiles, 3-bromo-N-(substituted)propanamides (7a−s), and these were further reacted with nucleophile 4 in DMF and NaH base to yield the targeted N-(substituted)-3-{(5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl)sulfanyl}propanamides (8a−s). The chemical structures of these biheterocyclic propanamides were confirmed by IR, 1 H NMR, 13 C NMR, and EI-MS spectral techniques. These compounds were evaluated for their enzyme inhibitory potentials against the αglucosidase enzyme, where the compound 8l showed promising enzyme inhibitory potential with an IC 50 value less than that of the standard acarbose. Molecular docking results of these molecules were coherent with the results of their enzyme inhibitory potentials. Cytotoxicity was assessed by the percentage of hemolytic activity method, and these compounds generally exhibited very low values as compared to the reference standard, Triton-X. Hence, some of these biheterocyclic propanamides might be considered as salient therapeutic agents in further stages of antidiabetic drug development.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity

et al. 2023

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“…Then, 20 L of the synthetic compound solution (10 mg/mL) in 180 L of RBCs suspension was added and incubated for 30 min at room temperature. PBS was used as negative control and Triton 100-X was taken as positive control [13,14]. The %age of hemolysis was taken through the formula:…”

Section: Hemolytic Activitymentioning

confidence: 99%

Synthesis and structure-activity relationship of 1-[(E)-3-phenyl-2-propenyl] piperazine derivatives as suitable antibacterial agents with mild hemolysis

et al. 2019

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A new series of 1-[(E)-3-phenyl-2-propenyl]piperazine derivatives (5a-m) as antibacterial agents was designed and synthesized. The synthetic strategy was initiated by coupling di erent anilines (1a-m) with bromoacetyl bromide (2) in an aqueous basic medium to acquire di erent electrophiles, 3a-m, with good yields. These electrophiles further reacted with 1-[(E)-3-phenyl-2-propenyl]piperazine (4) to yield the desired compounds, N-(substituted)-2-f4-[(E)-3-phenyl-2-propenyl]-1-perazinylg acetamides (5a-m). The structures of these compounds were established from their IR, 1 H-NMR, 13 C-NMR, EI-MS, and CHN analysis data. The bacterial bio lm inhibitory potential of these piperazine derivatives was tested against two pathogenic strains, Bacillus subtilus, and Escherichia coli. Two compounds, 5d and 5h, were identi ed as suitable antibacterial agents. The cytotoxicity of these molecules was pro led through hemolytic assay, and it was inferred that all the compounds were nearly harmless for membrane of red blood cells.

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“…The inhibitors of this enzyme can delay the release of D-glucose from oligosaccharides and disaccharides from dietary complex carbohydrates and delay glucose absorption, resulting in reduced postprandial hyperglycemia. Hence, the inhibition of a-glucosidase is an important step in the treatment of T2DM (Chapdelaine, Trembley, Dube, 1978;Abbasi et al, 2016). Several marketed drugs including acarbose and voglobiose are famous inhibitors of a-glucosidase.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study

Abbasi

Riaz

Rehman

et al. 2019

Braz. J. Pharm. Sci.

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The aim of the present research work was to investigate the enzyme inhibitory potential of some new sulfonamides having benzodioxane and acetamide moieties. The synthesis was started by the reaction of N-2,3-dihydrobenzo[1,4]-dioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) in the presence of 10% aqueous Na 2 CO 3 to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-methylbenzenesulfonamide (3), which was then reacted with 2-bromo-N-(un/substituted-phenyl)acetamides (6a-l) in DMF and lithium hydride as a base to afford various 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl)sulfonyl] amino}-N-(un/substituted-phenyl)acetamides (7a-l). All the synthesized compounds were characterized by their IR and 1 H-NMR spectral data along with CHN analysis data. The enzyme inhibitory activities of these compounds were tested against a-glucosidase and acetylcholinesterase (AChE). Most of the compounds exhibited substantial inhibitory activity against yeast a-glucosidase and weak against AChE. The in silico molecular docking results were also consistent with in vitro enzyme inhibition data.

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Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Abstract: Purpose: To synthesize a series of new N-(2,3-dimethylphenyl) 27.20 ± 0.24 to 5.20 ± 0.41 %,. Conclusion: Compound 5f is the most potent antibacterial while 5j is the best α-glucosidase inhibitor; 5e showed the least cytotoxicity.

Cited by 6 publications

References 17 publications

Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity

Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity

Synthesis and structure-activity relationship of 1-[(E)-3-phenyl-2-propenyl] piperazine derivatives as suitable antibacterial agents with mild hemolysis

Synthesis of new 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl) sulfonyl]amino}-N-(un/substituted-phenyl)acetamides as α-glucosidase and acetylcholinesterase inhibitors and their in silico study

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