Synthesis, biological evaluation (antioxidant, antimicrobial, enzyme inhibition, and cytotoxic) and molecular docking study of hydroxy methoxy benzoin/benzil analogous

Yaylı, Nurettin; Kılıç, Gözde; Kahriman, Nuran; Kanbolat, Seyda; Bozdeveci, Arif; Karaoğlu, Şengül Alpay; Aliyazıcıoğlu, Rezzan; Sellitepe, Hasan Erdinç; Doğan, İnci Selin; Aydın, Ali; Tatar, Gizem

doi:10.1016/j.bioorg.2021.105183

Cited by 7 publications

(8 citation statements)

References 76 publications

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“…Optical density (OD) was found to be 517 nm with a microplate reader. The IC50 values were computed with the formula above [22].…”

Section: Dpph Radical Scavenging Assay Of 15-28mentioning

confidence: 99%

“…The spectral data of already known methoxy chalcones (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) [19][20] and compounds 15-16 [14-15] have been reported. However, the spectral data of the all new methoxy DH-Pyr-S (17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28) are given in the experimental part. In the literature, DH-Pyr-S compounds have been synthesized by reflux, and MW methods [7-8, 10-11, 14-15].…”

Section: Chemistrymentioning

confidence: 99%

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MW Assisted Synthesis of New 4,6-diaryl-3,4-Didhydropyrimidines-2(1H)-thione Derivatives: Tyrosinase Inhibition, Antioxidant, and Molecular Docking Studies

FANDAKLI,

YÜCEL,

ÖZTÜRK

et al. 2023

Cumhuriyet Science Journal

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A number of new methoxy-substituted 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-thiones (DH-Pyr-S, 17-28) were designed and synthesized by the reaction of methoxy-substituted chalcones (1–14) with thiourea using solid-phase microwave method (MW) in view of the structural requirements as suggested in the pharmacophore model for tyrosinase inhibition (TI). Synthesized compounds were assessed for their in vitro TI potential and compounds 16, 17, and 21 exhibited notable tyrosinase inhibitory properties at the concentrations of 31.86 ± 2.45 µM, 44.58 ± 0.46 µM, and 48.47 ± 0.66 µM, respectively. Compounds (16, 17, and 21) were exhibited experimentally more potent TI than the standard used in terms of the IC50 value (Kojic acid, 55.38 ± 2.30 µM; p<0.0001). Additionally, DPPH activity of 15-28 were evaluated and compound 17 showed the moderate DPPH activity (45.64 ± 0.34%). Binding affinities of synthesized molecules to the tyrosinase catalytic core were further investigated through in silico molecular docking studies using AutoDock Vina (version 1.2.5), discovery studio accelyrs (BIOVIA, Dassault Systèmes) and predicting small-molecule pharmacokinetic properties using graph-based signatures (pkCSM) programs were used for ADMET calculations. Among synthesized compounds 15, 21, and 24 revealed high binding affinity to tyrosinase active site with lowest binding free energy (ΔG) values of -7.9 kcal/mol, thereby outperformed kojic acid affinity. In conclusion most modeling results were in agreement with their experimental data, suggesting the TI potential of lead compounds.

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“…Optical density (OD) was found to be 517 nm with a microplate reader. The IC50 values were computed with the formula above [22].…”

Section: Dpph Radical Scavenging Assay Of 15-28mentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

MW Assisted Synthesis of New 4,6-diaryl-3,4-Didhydropyrimidines-2(1H)-thione Derivatives: Tyrosinase Inhibition, Antioxidant, and Molecular Docking Studies

FANDAKLI,

YÜCEL,

ÖZTÜRK

et al. 2023

Cumhuriyet Science Journal

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“…A diverse array of biological and pharmacological effects can be attributed to heterocyclic substances. Scientists frequently utilise either solitary or merged forms of these entities to cultivate novel candidates with promising biological properties [16,17]. Several heterocycles with significant therapeutic potentials have been identified by several authors [18,19], encompassing several effective lead compounds with antidiabetic properties.…”

Section: Introductionmentioning

confidence: 99%

Electrostatic Potential Mapped onto Electron Density Surface, ADME, Molecular Docking and Molecular Dynamics Simulations of Some Indolin-2-one Analogues as Cytochrome C Peroxidase Inhibitors

Otuokere

2024

Preprint

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The transfer of cytochrome c (cyt c) from the mitochondria to the cytosol is commonly regarded as the final stage in the mitochondria-mediated apoptotic response, where there is no possibility of intervention. A potential approach for the development of antiapoptotic medicines involves the inhibition of cyt c interactions. Therefore, it is necessary to develop more effective pharmaceuticals that can inhibit the functioning of cytochrome c peroxidase. The PyRx virtual screening programme was used to conduct a molecular docking investigation on five indolin-2-one (IDL) analogues as inhibitors of cytochrome c peroxidase. The study on ADME was conducted via the SWISSADME server. The Schrondinger suite was utilized to do molecular dynamics (MD) analysis. The binding affinity of the five IDL analogues were − 14.0 to − 15.1 Kcal/mol. The interactions with the receptor (2X08) were facilitated through various mechanisms, including hydrophobic interactions, salt bridges, hydrogen bonds, π-stacking, and electrostatic bonds. These interactions were facilitated by the presence of specific amino acid residues, namely TRP 51A, PHE 158A, LEU 171A, ALA 174A, PHE 266A, PHE 266A, and LEU 239. The present study made predictions for the ADME features of the substances under investigation, revealing favourable pharmacokinetic characteristics. The study additionally predicted the drug-like characteristics of the compounds and determines their oral bioavailability, indicating favourable bioavailability ratings. The molecular dynamics simulations demonstrated the high stability of the optimal IDL analogue with the 2X08 binding pocket. It was concluded that these compounds could be used as potential drugs for the inhibition of cytochrome c peroxidase.

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“…5 Apart from that, benzimidazole moiety kept the attraction because of their various biological activities. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] The motivation behind this study is the mimic drugrepurposing strategy and keep the active pharmacophore rigid. Therefore, five new benzimidazole derivatives were designed and synthesized.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazole-tiyazol hibriti: sentez, yapı karakterizasyonu ve sitotoksik özellikler

et al. 2023

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Aim: Neuroblastoma is one of the leading tumors among the childhood cancers and the treatment of the disease is currently being investigated. As the metastatic ability of the cells is high, current anticancer therapy needs improvement. Method: Therefore, here five novel benzimidazole-thiazole compounds were synthesized. Their strucutres were elucidated using spectroscopic methods like FTIR, NMR and Mass analysis. The synthesis monitoring and purity of the compounds were performed with chromatographic methods. The compounds biological activity on SH-SY5Y neuroblastoma cell line was investigated using MTT assay. Results: All of the tested compounds showed moderate cytotoxic activity. The best IC50 was obtained from compound 6b with the IC50 value of 175,02±4,17 µM. Conclusion: These results indicated that benzimidazole-thiazole core is important for anti neuroblastoma activity, however, the ability of intramolecular hydrogen bonding could block the anticancer activity.

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Synthesis, biological evaluation (antioxidant, antimicrobial, enzyme inhibition, and cytotoxic) and molecular docking study of hydroxy methoxy benzoin/benzil analogous

Cited by 7 publications

References 76 publications

MW Assisted Synthesis of New 4,6-diaryl-3,4-Didhydropyrimidines-2(1H)-thione Derivatives: Tyrosinase Inhibition, Antioxidant, and Molecular Docking Studies

MW Assisted Synthesis of New 4,6-diaryl-3,4-Didhydropyrimidines-2(1H)-thione Derivatives: Tyrosinase Inhibition, Antioxidant, and Molecular Docking Studies

Electrostatic Potential Mapped onto Electron Density Surface, ADME, Molecular Docking and Molecular Dynamics Simulations of Some Indolin-2-one Analogues as Cytochrome C Peroxidase Inhibitors

Benzimidazole-tiyazol hibriti: sentez, yapı karakterizasyonu ve sitotoksik özellikler

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