Arylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities

Koçyiğit, Ümit M.; Ökten, Salih; Çakmak, Osman; Burhan, Gizem; Ataş, Mehmet; Taslimi, Parham; Gülçın, İlhami

doi:10.1002/slct.202203469

Cited by 12 publications

(14 citation statements)

References 43 publications

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“…For respiration, it facilitates the lungs with the accumulation of CO 2 . In stomach, it helps in the formation of hydrochloric acid, and in renal tubule it maintains the concentration of protons, bicarbonates and other electrolytes [7,8] . CA inhibitors are the therapeutic agents used to control the hyper activity of CA.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Bioactivity Impacts of New Anthranilic Acid Hydrazones Containing Aryl Sulfonate Moiety as Fenamate Isosteres

Tokalı¹,

Taslimi²,

Sadeghian³

et al. 2023

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In this study, it was planned to synthesize new members of fenamate isosteres and investigate its effect on some metabolic enzymes such as Acetylcholinesterase, Butyrylcholinesterase, α‐Glucosidase, Carbonic andyhrase I–II. The target compounds were obtained from the reaction of N‐subtituted anthranilic hydrazides with sulfonylated aldehyde derivatives. The structures of the compounds were characterized using Fourier‐transform Infrared, Nuclear Magnetic Resonance, and High‐resolution Mass Spectroscopy. Compounds had potent inhibitory strength with Ki values in the range of 0.23±0.03–7.12±0.41 μM against carbonic anhydrase‐I and 0.13±0.01–6.21±0.52 μM against carbonic anhydrase‐II. Compounds inhibited acetycholinesterase and butyrylcholinesterase with the Ki values in the range of 42.73±15.80 nM–977.52±32.67 nM and 25.84±4.09 nM–261.36±34.05 nM, respectively. All compounds showed potent inhibitory activity against α‐glucosidase enzyme with IC50 value 1.51–23.51 nM, compared to the standard acarbose (64.53 nM). The orientation of binding of the synthesized compounds were further appraised by molecular docking studies, which reflects the importance of sulfonyl, furan, thiophene, and methoxy groups in protein‐ligand interaction. The docking results are complementary with the Ki values of compounds while the interaction pattern of the current compounds clearly indicates their structure‐activity relationship.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Bioactivity Impacts of New Anthranilic Acid Hydrazones Containing Aryl Sulfonate Moiety as Fenamate Isosteres

Tokalı¹,

Taslimi²,

Sadeghian³

et al. 2023

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“…This enzyme has been linked to therapeutic targets for AD [ 70 , 71 ]. The hypothesis was put forth to explain AD that synaptic depression is hampered because the cholinergic neuron cells impede ACh hydrolysis [ 72 , 73 ]. ACh hydrolysis is hindered because of AChE inhibition.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Bromophenol with Diaryl Methanes—Determination of Their Inhibition Effects on Carbonic Anhydrase and Acetylcholinesterase

et al. 2022

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In this work, nine new bromophenol derivatives were designed and synthesized. The alkylation reactions of (2-bromo-4,5-dimethoxyphenyl)methanol (7) with substituted benzenes 8–12 produced new diaryl methanes 13–17. Targeted bromophenol derivatives 18–21 were synthesized via the O-Me demethylation of diaryl methanes with BBr3. Moreover, the synthesized bromophenol compounds were tested with some metabolic enzymes such as acetylcholinesterase (AChE), carbonic anhydrase I (CA I), and II (CA II) isoenzymes. The novel synthesized bromophenol compounds showed Ki values that ranged from 2.53 ± 0.25 to 25.67 ± 4.58 nM against hCA I, from 1.63 ± 0.11 to 15.05 ± 1.07 nM against hCA II, and from 6.54 ± 1.03 to 24.86 ± 5.30 nM against AChE. The studied compounds in this work exhibited effective hCA isoenzyme and AChE enzyme inhibition effects. The results show that they can be used for the treatment of glaucoma, epilepsy, Parkinson’s as well as Alzheimer’s disease (AD) after some imperative pharmacological studies that would reveal their drug potential.

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“…The antimicrobial activity of the WEZP, EEZP, and P. granatum juice was determined by a disk diffusion method [ 72 ]. The test microorganism agar cultures were prepared in accordance with the procedure described by Gulcin et al [ 73 ]. Bacterial strains were grown on blood agar medium (Oxoid CM55, Basingstoke, Hampshire, UK).…”

Section: Methodsmentioning

confidence: 99%

Determination of Antioxidant, Anti-Alzheimer, Antidiabetic, Antiglaucoma and Antimicrobial Effects of Zivzik Pomegranate (Punica granatum)—A Chemical Profiling by LC-MS/MS

Karageçili

İzol

Kıreçcı

et al. 2023

Life

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Zivzik pomegranate (Punica granatum) has recently sparked considerable interest due to its nutritional and antioxidant properties. To evaluate the antioxidant capacities of P. granatum juice, ethanol (EEZP), and water (WEZP) extracts from peel and seed, the antioxidant methods of 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid radical (ABTS•+) scavenging, 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH•) scavenging, Fe3+-2,4,6-tris(2-pyridyl)-S-triazine (TPTZ) reducing, Fe3+ reducing, and Cu2+ reducing methods were used. The antioxidant capacities of samples were compared with the most commonly used synthetic antioxidants, i.e., BHA, BHT, α-tocopherol, and Trolox. In terms of setting an example, the IC50 values of EEZP for ABTS•+ and DPPH• scavenging activities were found to be lower than standards, at 5.9 and 16.1 μg/mL, respectively. The phenolic and flavonoid contents in EEZP peel were 59.7 mg GAE/g and 88.0 mg QE/g, respectively. Inhibition of α-glycosidase, α-amylase, acetylcholinesterase, and human carbonic anhydrase II (hCA II) enzymes was also investigated. EEZP demonstrated IC50 values of 7.3 μg/mL against α-glycosidase, 317.7 μg/mL against α-amylase, 19.7 μg/mL against acetylcholinesterase (AChE), and 106.3 μg/mL against CA II enzymes. A total of 53 phenolic compounds were scanned, and 30 compounds were determined using LC-MS/MS. E. coli and S. aureus bacteria were resistant to all four antibiotics used as standards in hospitals.

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Arylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities

Cited by 12 publications

References 43 publications

Synthesis, Characterization, Bioactivity Impacts of New Anthranilic Acid Hydrazones Containing Aryl Sulfonate Moiety as Fenamate Isosteres

Synthesis, Characterization, Bioactivity Impacts of New Anthranilic Acid Hydrazones Containing Aryl Sulfonate Moiety as Fenamate Isosteres

Synthesis of Novel Bromophenol with Diaryl Methanes—Determination of Their Inhibition Effects on Carbonic Anhydrase and Acetylcholinesterase

Determination of Antioxidant, Anti-Alzheimer, Antidiabetic, Antiglaucoma and Antimicrobial Effects of Zivzik Pomegranate (Punica granatum)—A Chemical Profiling by LC-MS/MS

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