Synthesis, Structural Elucidation and Anti-Bacterial Evaluation of Fluorinated and Non-Fluorinated Schiff Bases of Quinazoline-4(3H)-One

In this study, imines bearing quinazolin‐4(3H)‐one were synthesized and their inhibitory properties were investigated against some metabolic enzymes including Acetylcholinesterase (AChE), Butyrylcholinesterase (BChE), α‐Glycosidase (α‐Gly), and human Carbonic Anhydrase I–II (hCA I–II). All compounds had inhibitory strength with Ki values in the range of 38.55±4.08–159.05±10.68 nM and 41.04±6.73–177.12±8.06 nM against hCA I and hCA‐II, respectively in comparison to the standard acetazolamide (AZA) Ki=125.15±0.78 nM (for hCA‐I) and Ki=148.75±0.92 nM (for hCA‐II). The compounds showed potent inhibitory activity against α‐Gly enzyme with IC50 value 0.34–2.28 nM (standard inhibitor acarbose (ACR): 3.18 nM). Also, these analogs had potent inhibitory strength with Ki values in the range of 4.20±0.15–26.10±2.36 nM against AChE and 1.22±0.05–16.09±0.88 nM against BChE in comparison to the standard tacrine (TAC) Ki=37.62±6.86 nM (for AChE) and Ki=26.75±5.79 nM (for BChE). Additionally, the molecular docking and molecular dynamics simulation study was carried out for the determination of ligand‐enzyme interactions. The docking scores of the most active compound were calculated as −7.31, −7.59, −6.66, −6.93 and −7.11 kcal/mol for AChE, BChE, hCA I, hCA II, and α‐Gly, respectively.

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“…The IC 50 and K i plots of the compounds 3a‐s are also seen in SI. Additional references cited within the Supporting Information [54,55] …”

Section: Supporting Information Summarymentioning

confidence: 99%

Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

Tokalı¹,

Taslimi²,

Sadeghi

et al. 2023

ChemistrySelect

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Quinoline-based anti-MRSA agents: Current development, structure-activity relationships, and mechanisms

Cui

Liu

et al. 2024

Chinese Chemical Letters

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3,4-difluoro-2-(((4-phenoxyphenyl)imino)methyl)phenol with in silico predictions: Synthesis, spectral analyses, ADME studies, targets and biological activity, toxicity and adverse effects, site of metabolism, taste activity

Şahin

2024

Journal of Molecular Structure

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Synthesis, Structural Elucidation and Anti-Bacterial Evaluation of Fluorinated and Non-Fluorinated Schiff Bases of Quinazoline-4(3H)-One

Cited by 3 publications

References 22 publications

Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

Synthesis and Evaluation of Quinazolin‐4(3H)‐one Derivatives as Multitarget Metabolic Enzyme Inhibitors: A Biochemistry‐Oriented Drug Design

Quinoline-based anti-MRSA agents: Current development, structure-activity relationships, and mechanisms

3,4-difluoro-2-(((4-phenoxyphenyl)imino)methyl)phenol with in silico predictions: Synthesis, spectral analyses, ADME studies, targets and biological activity, toxicity and adverse effects, site of metabolism, taste activity

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