Thiazolyl-pyrazoline derivatives: In vitro and in silico evaluation as potential acetylcholinesterase and carbonic anhydrase inhibitors

Sever, Belgin; Türkeş, Cüneyt; Altıntop, Mehlika Dilek; Demir, Yeliz; Beydemır, Şükrü

doi:10.1016/j.ijbiomac.2020.09.043

Cited by 89 publications

(78 citation statements)

References 90 publications

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“…Besides, the -NH-and -NH2 groups of pyrazoline assigned to a signal as broad at 5.9-6.2 ppm. According to the previous reports, the formation of pyrazoline scaffold in the final compounds was confirmed, in which N-H protons determined at 7.89 ppm by broad singlet (Sever et al, 2020). The 13 C NMR spectra were further supported all structures which gave the chemical shift values of carbon atoms of pyrazoline ring C-3 at 150.1-153.9 ppm, C-4 at 40.2-43.2 ppm, and C-5 at 56.9-62.7 ppm.…”

Section: Figuresupporting

confidence: 66%

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

Çelik¹

2021

Gümüşhane Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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Pyrazolines, which are nitrogen including five-membered heterocyclic structures, have been used in the organic and pharmaceutical industries. This study aimed was to synthesize and characterizes new series of 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives. The new pyrazoline compounds have been synthesized from chalcones and hydrazine hydrate in two steps. In the first step, chalcones were synthesized from 2-amino acetophenone and various substituted benzaldehyde by Claisen-Schmidt condensation at room temperature. In second step, starting from various substituted chalcones derivatives with hydrazine hydrate and glacial acetic acid in anhydrous ethanol were synthesized six novel 3,5diphenyl-4,5-dihydro-1H-pyrazole derivatives utilizing intramolecular Michael addition reaction in good yields. The structures of the newly synthesized 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives are identified via 1H NMR, 13C NMR, FT-IR, and HRMS.

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Section: Figuresupporting

confidence: 66%

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

Çelik¹

2021

Gümüşhane Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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“…Physicochemical and ADME‐Tox properties of novel substituted phenylureido sulfaguanidine derivatives ( 2a – 2f ) including lipophilicity, solubility, metabolic liabilities, drug‐likeness, and pan‐assay interference compounds alert were calculated using the QikProp tool [56] of Schrödinger Suite 2020‐3 for Mac (Schrödinger, LLC, NY, USA) and SwissADME platform [57,58] …”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Inhibition Study of Novel Substituted Phenylureido Sulfaguanidine Derivatives as α‐Glycosidase and Cholinesterase Inhibitors

Akocak

Taslimi

Lolak

et al. 2021

Chemistry & Biodiversity

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A series of six N‐carbamimidoyl‐4‐(3‐substituted phenylureido)benzenesulfonamide derivatives were synthesized by reaction of sulfaguanidine with aromatic isocyanates. In vitro and in silico inhibitory effects of the novel ureido‐substituted sulfaguanidine derivatives were investigated by spectrophotometric methods for α‐glycosidase (α‐GLY), acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) enzymes associated with diabetes mellitus (DM) and Alzheimer's disease (AD). N‐Carbamimidoyl‐4‐{[(3,4‐dichlorophenyl)carbamoyl]amino}benzene‐1‐sulfonamide (2f) showed AChE and BChE inhibitory effects, with KI values of 515.98±45.03 nM and 598.47±59.18 nM, respectively, while N‐carbamimidoyl‐4‐{[(3‐chlorophenyl)carbamoyl]amino}benzene‐1‐sulfonamide (2e) showed strong α‐GLY inhibitory effect, with KI values of 103.94±13.06 nM. The antidiabetic effects of the novel synthesized compounds are higher than their anti‐Alzheimer's effects, because the inhibition effect of the compounds on the α‐GLY with diabetic enzyme is greater than the effect on esterase enzymes. Indeed, inhibition of the metabolic enzymes is important for the treatment of DM and AD.

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“…In this study, the procedures applied in synthesis, biological assay, and in silico analyses were provided in the Supporting Information [25–64] …”

Section: Resultsmentioning

confidence: 99%

Transition‐Metal Complexes of Bidentate Schiff‐Base Ligands: In Vitro and In Silico Evaluation as Non‐Classical Carbonic Anhydrase and Potential Acetylcholinesterase Inhibitors

et al. 2021

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Schiff bases display superior features for many areas, such as significant intermediates in industrial biological, pharmacological, catalytic and optical properties, organic synthesis, and coordination chemistry. The pre‐synthesized two Schiff base ligands (HL1 and HL2) and their bidentate metal complexes (Co(L1)2, Cu(L1)2, Ni(L1)2, Co(L2)2, Cu(L2)2, and Ni(L2)2) were tested for their inhibition activities on acetylcholinesterase (AChE) and human carbonic anhydrase (hCA I and hCA II) isoforms. The transition metal complexes of bidentate Schiff base ligands displayed the potent inhibition effect with KI constants ranging from 16.39±0.15 to 88.63±0.27 nM and 9.32±0.13 to 33.66±0.57 nM for hCA isoenzymes and AChE, respectively. The compound Cu(L1)2 for hCA I and Ni(L2)2 for AChE and hCA II had the highest inhibitory effect. Besides, the molecular docking analyses of the most active complexes (Cu(L1)2 and Ni(L2)2) were performed to understand the binding interactions on the enzymes’ binding sites. According to both in vitro and in silico analysis results, all the compounds were potential inhibitors of AChE and hCA I, II isoenzymes.

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Thiazolyl-pyrazoline derivatives: In vitro and in silico evaluation as potential acetylcholinesterase and carbonic anhydrase inhibitors

Cited by 89 publications

References 90 publications

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

Synthesis, Characterization, and Inhibition Study of Novel Substituted Phenylureido Sulfaguanidine Derivatives as α‐Glycosidase and Cholinesterase Inhibitors

Transition‐Metal Complexes of Bidentate Schiff‐Base Ligands: In Vitro and In Silico Evaluation as Non‐Classical Carbonic Anhydrase and Potential Acetylcholinesterase Inhibitors

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