Synthesis and Molecular Docking Study of Some New 4-{[4-(2-Furoyl)- 1-piperazinyl]methyl}-N-(substituted-phenyl)benzamides as Possible Therapeutic Entrants for Alzheimer’s Disease

Hussain, Ghulam

doi:10.4172/2161-0444.1000337

Cited by 7 publications

(1 citation statement)

References 14 publications

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“…The stable and polar amide functionality is an important unit among the organic molecules of natural occurrence (e.g., peptides and proteins). It is also found in many synthetic substances of therapeutic interests [9].…”

Section: Introductionmentioning

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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Section: Introductionmentioning

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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Bi‐heterocyclic benzamides as alkaline phosphatase inhibitors: Mechanistic comprehensions through kinetics and computational approaches

Abbasi

Nazir

Ur-Rehman

et al. 2019

Archiv der Pharmazie

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Novel bi‐heterocyclic benzamides were synthesized by sequentially converting 4‐(1H‐indol‐3‐yl)butanoic acid (1) into ethyl 4‐(1H‐indol‐3‐yl)butanoate (2), 4‐(1H‐indol‐3‐yl)butanohydrazide (3), and a nucleophilic 5‐[3‐(1H‐indol‐3‐yl)propyl]‐1,3,4‐oxadiazole‐2‐thiol (4). In a parallel series of reactions, various electrophiles were synthesized by reacting substituted anilines (5a–k) with 4‐(chloromethyl)benzoylchloride (6) to afford 4‐(chloromethyl)‐N‐(substituted‐phenyl)benzamides (7a–k). Finally, the nucleophilic substitution reaction of 4 was carried out with newly synthesized electrophiles, 7a–k, to acquire the targeted bi‐heterocyclic benzamides, 8a–k. The structural confirmation of all the synthesized compounds was done by IR, 1H NMR, 13C NMR, EI‐MS, and CHN analysis data. The inhibitory effects of these bi‐heterocyclic benzamides (8a–k) were evaluated against alkaline phosphatase, and all these molecules were identified as potent inhibitors relative to the standard used. The kinetics mechanism was ascribed by evaluating the Lineweaver–Burk plots, which revealed that compound 8b inhibited alkaline phosphatase non‐competitively to form an enzyme–inhibitor complex. The inhibition constant Ki calculated from Dixon plots for this compound was 1.15 μM. The computational study was in full agreement with the experimental records and these ligands exhibited good binding energy values. These molecules also exhibited mild cytotoxicity toward red blood cell membranes when analyzed through hemolysis. So, these molecules might be deliberated as nontoxic medicinal scaffolds to render normal calcification of bones and teeth.

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Synthesis, Kinetics and Computational Explorations of 4‐Phenylpiperazine Bearing N‐(Aryl)‐3‐substituted‐benzamides as Auspicious Tyrosinase Inhibitors

Zeb,

Abbasi,

Aziz‐ur‐Rehman

et al. 2024

Chemistry & Biodiversity

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In the aimed research study, a new series of N‐(aryl)‐3‐[(4‐phenyl‐1‐piperazinyl)methyl]benzamides was synthesized, which was envisaged as tyrosinase inhibitor. The structures of these newly designed molecules were verified by IR, 1H‐NMR, 13C‐NMR, EI‐MS and CHN analysis data. These molecules were screened against tyrosinase and their inhibitory activity explored that these 3‐substituted‐benzamides exhibit good to excellent potential, comparative to the standard. The Kinetics mechanism was investigated through Lineweaver‐Burk plots which depicted that molecules inhibited this enzyme in a competitive mode. Moreover, molecular docking was also performed to determine the binding interaction of all synthesized molecules (ligands) with the active site of tyrosinase enzyme and the results showed that most of the ligands exhibited efficient binding energy values. Therefore, it is anticipated that these molecules might serve as auspicious therapeutic scaffolds for treatment of the tyrosinase associated skin disorders.

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Synthesis and Molecular Docking Study of Some New 4-{[4-(2-Furoyl)- 1-piperazinyl]methyl}-N-(substituted-phenyl)benzamides as Possible Therapeutic Entrants for Alzheimer’s Disease

Cited by 7 publications

References 14 publications

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

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

Bi‐heterocyclic benzamides as alkaline phosphatase inhibitors: Mechanistic comprehensions through kinetics and computational approaches

Synthesis, Kinetics and Computational Explorations of 4‐Phenylpiperazine Bearing N‐(Aryl)‐3‐substituted‐benzamides as Auspicious Tyrosinase Inhibitors

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