Probing 2-acetylbenzofuran hydrazones and their metal complexes as α-glucosidase inhibitors

Khan, Samra; Tariq, Muhammad; Ashraf, Muhammad; Abdullah, Shawana; al‐Rashida, Mariya; Khalid, Muhammad; Taslimi, Parham; Fatima, Mehwish; Zafar, Rafia; Shafiq, Zahid

doi:10.1016/j.bioorg.2020.104082

Cited by 43 publications

(30 citation statements)

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“…[43][44][45] Alzheimer's disease (AD) is a progressive degenerative disease that first begins with memory loss and eventually affects all cognition and behavior with a prevalence of over 40 million people worldwide is one of the most common age-related diseases. [46][47][48] This disease is characterized by progressive memory loss, various cognitive impairments, and a decline in language skills. It is one of the most common forms of dementia, which affects millions of people worldwide and has become one of the serious health problems among elderly people.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Tezcan

Gök

Sevinçek

et al. 2022

J Biochem & Molecular Tox

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Here, we report the synthesis, characterization, and biological activities of a series of benzimidazolium salts bearing the trifluoromethylbenzyl group. All benzimidazolium salts were characterized by using nuclear magnetic resonance (NMR) ( 1 H NMR and 13 C NMR), Fourier transform-infrared spectroscopy, and elemental analysis techniques. The crystal structures of some of these compounds were obtained by the single-crystal X-ray diffraction method. Furthermore, the acetylcholinesterase (AChE) and α-glycosidase (α-Gly) enzyme inhibition activities of these compounds were investigated. The obtained results revealed that 2e, with K i value of 1.36 ± 0.34 µM against AChE and 3d with K i value of 91.37 ± 10.38 µM against α-Gly, were the most potent compounds against both assigned enzymes. It should be noted that most of the synthesized compounds were more potent than standard inhibitor tacrine (TAC) against AChE. In silico studies, we focused on compound 2e, 3d, 3e, and 3f as potent inhibitors of AChE and α-Gly, the compound 2e showed good binding energy (−10.23 kcal/mol), among the three selected compounds and positive control (−10.18, −10.08, and −7.37 kcal/mol for 3d, 3f, and TAC, respectively). Likewise, as a result of the same compounds against the α-Gly enzyme, the compound 3d had the highest binding affinity (−8.39 kcal/mol) between the four selected compounds and the positive control (−8.27, −8.10, −8.06, and −7.53 kcal/mol for 3f, 3e, 2e, and acarbose, respectively). From the absorption, distribution, metabolism, excretion, and toxicity analyses, it can be concluded that the compounds under consideration exhibited more drug-likeness properties in the prediction studies compared to positive controls.

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Section: Introductionmentioning

confidence: 99%

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Tezcan

Gök

Sevinçek

et al. 2022

J Biochem & Molecular Tox

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“…The measurements were spectrophotometrically recorded at 348 nm. [ 55–57 ] However, the inhibitory effects of AChE from electric eel ( Electrophorus electricus ) and BChE from equine serum were determined according to the method of Ellman et al [ 58 ] They were recorded spectrophotometrically at 412 nm using acetylthiocholine iodide and butyrylcholine iodide, and recorded as enzymatic reaction substrates according to previous studies. 5,5ʹ‐Dithio‐bis(2‐nitro‐benzoic acid) was used as a substrate to measure AChE activity.…”

Section: Methodsmentioning

confidence: 99%

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Mirzazadeh

Asgari

Barzegari

et al. 2021

Archiv der Pharmazie

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A new series of quinoxalin‐1,3,4‐oxadiazole (10a–l) derivatives was synthesized and evaluated against some metabolic enzymes including human carbonic anhydrase (hCA) isoenzymes I and II (carbonic anhydrases I and II), cholinesterase (acetylcholinesterase and butyrylcholinesterase), and α‐glucosidase. Obtained data revealed that all the synthesized compounds were more potent as compared with the used standard inhibitors against studied target enzymes. Among the synthesized compounds, 4‐fluoro derivative (10f) against hCA I, 4‐chloro derivative (10i) against hCA II, 3‐fluoro derivative (10e) against acetylcholinesterase and butyrylcholinesterase, and 3‐bromo derivative (10k) against α‐glucosidase were the most potent compounds with inhibitory activity around 1.8‐ to 7.37‐fold better than standard inhibitors. Furthermore, docking studies of these compounds were performed at the active site of their target enzymes.

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“…In recent years, the metal ions play important role in living systems and various transition metal complexes have been used as medicinal compounds. Metal complexes possess great diversity in their action like anticancer [18], anti-inflammatory [19], antimycotic [20], anti-alzheimer [21], anti-oxidant, anti-microbial [22] and anti-diabetic [23] properties. Metal ions play vital roles in biological processes, for instance the divalent magnesium and calcium ions play important regulatory roles in cells.…”

Section: Introductionmentioning

confidence: 99%

Preparation, spectral study and antimicrobial activity of binary Co(II) complexes derived from 2’-hydroxy chalcones

Patil¹,

Zangade²

2022

Bull. Chem. Soc. Eth.

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ABSTRACT. The present work comprises preparation, characterization, thermal behavior and growth inhibitory activity of some novel Co(II) complexes derived from substituted (E)-1-(1-hydroxy-4-iodonaphthalen-2-yl)-3-phenylprop-2-en-1-one (L1) and (E)-1-(4-bromo-1-hydroxynaphthalen-2-yl)-3-phenylprop-2-en-1-one (L2-L6). Newly synthesized metal-ligand complexes were structurally confirmed with suitable spectroscopic technique such as FT-IR, EPR, NMR (both 1H and 13C). XRD analysis for complex C1 confirmed the crystal system; tetragonal and space group; P 42/n: 2 with unit cell dimensions a, b = 13.3516 Å, c = 10.8009 Å; α, β, γ = 90o. The IR and EPR study demonstrated that interaction between metal ions and ligand occurs through carbonyl oxygen and hydroxyl oxygen. From the values of magnetic moment (μ) it was observed that synthesized complexes (C1-C6) are paramagnetic with three unpaired electrons contain one electron in t2g orbital and two electrons in eg orbitals. Further all these complexes have been evaluated in-vitro for their antimicrobial activity against the Gram positive bacteria Staphylococcus aureus, Gram negative bacteria Escherichia coli and the yeast Candida albicans. The complex C1 showed the significant antimicrobial activity, whereas the complexes C2, C4, C5 and C6 are moderately active against the tested pathogens. The antimicrobial data revealed that growth inhibitory activities of complexes were enhanced comparatively than its respective ligands. The enhanced antimicrobial activity is attributed to the presence of halogens (Br, Cl, I) and hydroxyl (OH) active substituents associated with the basic nucleus of complexes. Therefore, the present study helps to develop a new class of antimicrobial analogues. KEY WORDS: Metal complexes synthesis, 1,3-Diaryl-2-propene-1-one, Crystal structure, Thermal properties, Antimicrobial activity Bull. Chem. Soc. Ethiop. 2021, 35(3), 513-524. DOI: https://dx.doi.org/10.4314/bcse.v35i3.4

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Probing 2-acetylbenzofuran hydrazones and their metal complexes as α-glucosidase inhibitors

Cited by 43 publications

References 33 publications

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Preparation, spectral study and antimicrobial activity of binary Co(II) complexes derived from 2’-hydroxy chalcones

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