Metal‐Free Synthesis via Intramolecular Cyclization, Enzyme Inhibition Properties and Molecular Docking of Novel Isoindolinones

Atmaca, Ufuk; Kaya, Rüya; Sert, Yusuf; Çelik, M.; Gülçın, İlhami

doi:10.1002/slct.202204578

Cited by 13 publications

(6 citation statements)

References 99 publications

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“…Molecular docking provides useful information about the interactions between compounds with macromolecules ( Yiugit et al, 2019 ; Atmaca et al, 2023 ; Zengin et al, 2023 ). In addition, the involved amino acids in these interactions and protein active sites can be denoted by this technique.…”

Section: Resultsmentioning

confidence: 99%

RETRACTED: Spectroscopic and molecular modeling studies of binding interaction between the new complex of yttrium and 1,10-phenanthroline derivatives with DNA and BSA

Khorshidi,

Asadpour,

Aramesh-Boroujeni

et al. 2023

Front. Chem.

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In this study, the 4,9 diazafluoren-9-one ligand and [Y(Daf)2Cl3.OH2] complex were synthesized. The interaction of this complex with DNA and bovine serum albumin (BSA) was investigated by UV-vis and fluorescence spectroscopy. The molecular docking method was used to confirm the experimental results, investigate the type of interaction, and determine the binding site. The binding constant and Stern–Volmer constant were calculated using spectroscopy techniques. The binding constant of the Y-complex with DNA and BSA obtained using the UV-vis technique was 1.61 × 105 M−1 and 0.49 × 105 M−1, while that obtained using the fluorescence method was 3.39 × 105 M−1 and 3.63 × 105 M−1, respectively. The results of experimental and theoretical data showed that the interaction between the yttrium complex and DNA and BSA is driven by the hydrogen bond and van der Waals interaction, respectively. The yttrium complex communicates with DNA via the groove interaction. This complex has high binding energy with bovine serum albumin. In addition, the molecular docking results showed that the complex binds to the IIA subdomain of BSA (site I). Finally, anticancer activity of the yttrium complex was studied on MCF-7 and A549 cell lines by using the MTT method. The IC50 values obtained showed that the yttrium complex possesses anticancer activity.

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Section: Resultsmentioning

confidence: 99%

RETRACTED: Spectroscopic and molecular modeling studies of binding interaction between the new complex of yttrium and 1,10-phenanthroline derivatives with DNA and BSA

Khorshidi,

Asadpour,

Aramesh-Boroujeni

et al. 2023

Front. Chem.

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“…It was claimed that hCA II causes glaucoma and impaired vision by increasing HCO 3 − secretion in the eye’s anterior uvea. They are involved in the secretion of bicarbonate from the exocrine glands in the digestive system [ 81 ]. They play a role in regulating the acidity of gastric juice and in the secretion of mucus and bicarbonate from epithelial cells on tissue surfaces in the gastrointestinal tract.…”

Section: Discussionmentioning

confidence: 99%

Screening of Antiglaucoma, Antidiabetic, Anti-Alzheimer, and Antioxidant Activities of Astragalus alopecurus Pall—Analysis of Phenolics Profiles by LC-MS/MS

et al. 2023

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Astragalus species are traditionally used for diabetes, ulcers, leukemia, wounds, stomachaches, sore throats, abdominal pain, and toothaches. Although the preventive effects of Astragalus species against diseases are known, there is no record of the therapeutic effects of Astragalus alopecurus. In this study, we aimed to evaluate the in vitro antiglaucoma, antidiabetic, anti-Alzheimer’s disease, and antioxidant activities of the methanolic (MEAA) and water (WEAA) extracts of the aerial part of A. alopecurus. Additionally, its phenolic compound profiles were analyzed by liquid chromatography–tandem mass spectrometry (LC–MS/MS). MEAA and WEAA were evaluated for their inhibition ability on α-glycosidase, α-amylase, acetylcholinesterase (AChE), and human carbonic anhydrase II (hCA II) enzymes. The phenolic compounds of MEAA were analyzed by LC-MS/MS. Furthermore, total phenolic and flavonoid contents were determined. In this context, the antioxidant activity was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), N,N-dimethyl-p-phenylene diamine (DMPD), ferric reducing antioxidant power (FRAP), cupric ions (Cu2+) reducing antioxidant capacity (CUPRAC), ferric ions (Fe3+) reducing, and ferrous ions (Fe2+) chelating methods. MEAA and WEAA had IC50 values of 9.07 and 2.24 μg/mL for α-glycosidase, 693.15 and 346.58 μg/mL for α-amylase, 1.99 and 2.45 μg/mL for AChE, and 147.7 and 171.7 μg/mL for hCA II. While the total phenolic amounts in MEAA and WEAA were 16.00 and 18.50 μg gallic acid equivalent (GAE)/mg extract, the total flavonoid contents in both extracts were calculated as 66.23 and 33.115 μg quercetin equivalent (QE)/mg, respectively. MEAA and WEAA showed, respectively, variable activities on DPPH radical scavenging (IC50: 99.02 and 115.53 μg/mL), ABTS radical scavenging (IC50: 32.21 and 30.22 µg/mL), DMPD radical scavenging (IC50: 231.05 and 65.22 μg/mL), and Fe2+ chelating (IC50: 46.21 and 33.01 μg/mL). MEAA and WEAA reducing abilities were, respectively, Fe3+ reducing (λ700: 0.308 and 0.284), FRAP (λ593: 0.284 and 0.284), and CUPRAC (λ450: 0.163 and 0.137). A total of 35 phenolics were scanned, and 10 phenolic compounds were determined by LC-MS/MS analysis. LC-MS/MS revealed that MEAA mainly contained isorhamnetin, fumaric acid, and rosmarinic acid derivatives. This is the first report indicating that MEAA and WEAA have α-glycosidase, α-amylase, AChE, hCA II inhibition abilities, and antioxidant activities. These results demonstrate the potential of Astragalus species through antioxidant properties and enzyme inhibitor ability traditionally used in medicine. This work provides the foundation for further research into the establishment of novel therapeutics for diabetes, glaucoma, and Alzheimer’s disease.

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“…(Scheme 17). [35] A range of novel 3-hydroxyisoindolinones could be generated by intramolecular cyclization reaction under metal-free conditions with short reaction time, which provides a beneficial and practical method for the synthesis of involving 3-hydroxyisoindolinone derivatives in pharmaceuticals, and industrial applications. In addition, the biological activity of these novel synthesized compounds has also been investigated by testing against some metabolic enzymes.…”

Section: Scheme 16 Ru-catalyzed Synthesis Of Chiral Isoindolinonesmentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocycles from 2-Acylbenzoic Acids

Liu,

Li,

Yang

2024

Preprint

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Heterocyclics are the crucial scaffolds present in pharmaceuticals, natural products, biologically active compounds and agrochemicals. Consequently, the development of simple and practical methods for constructing heterocyclics has always been a fascinating field in organic synthesis. Recently, 2-acylbenzoic acids as highly reactive and versatile synthons have been broadly applied in the construction of heterocycles due to their multiple reaction sites. In this review, we summarized recent progress in the application of 2-acylbenzoic acids for the synthesis of heterocycles including phthalides, isochromanones, isoindolines, phthalazinones, and quinolones. The sub-strate scopes, proposed mechanisms, and product application of different types of reactions are discussed.

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Metal‐Free Synthesis via Intramolecular Cyclization, Enzyme Inhibition Properties and Molecular Docking of Novel Isoindolinones

Cited by 13 publications

References 99 publications

RETRACTED: Spectroscopic and molecular modeling studies of binding interaction between the new complex of yttrium and 1,10-phenanthroline derivatives with DNA and BSA

RETRACTED: Spectroscopic and molecular modeling studies of binding interaction between the new complex of yttrium and 1,10-phenanthroline derivatives with DNA and BSA

Screening of Antiglaucoma, Antidiabetic, Anti-Alzheimer, and Antioxidant Activities of Astragalus alopecurus Pall—Analysis of Phenolics Profiles by LC-MS/MS

Recent Advances in the Synthesis of Heterocycles from 2-Acylbenzoic Acids

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