Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives

Ivanenkov, Yan A.; Veselov, Mark S.; Rezekin, Igor G.; Skvortsov, Dmitry A.; Sandulenko, Yuri; Polyakova, M. V.; Bezrukov, Dmitry S.; Vasilevsky, Sergey V.; Kukushkin, Maxim E.; Moiseeva, Anna A.; Finko, Alexander V.; Koteliansky, Victor; Klyachko, Natalia L.; Filatova, L. Yu.; Белоглазкина, Е. К.; Зык, Н. В.; Majouga, Alexander G.

doi:10.1016/j.bmc.2015.12.050

Cited by 28 publications

(23 citation statements)

References 36 publications

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“…The selone analogue of chrysin and tetramethylquercetin has been synthesized and this compound exhibited better antioxidant activity, cytotoxicity and in specific the IC 50 in MCF-7 cells was lowered (Martins et al 2015). Selenohydantoin another compound was evaluated in vitro against many cancer cell lines and they showed excellent anti-proliferative activities in low μM concentrations (Ivanenkov et al 2016).…”

Section: Selenocarbonyl Derivativesmentioning

confidence: 99%

Selenium and selenoproteins: it’s role in regulation of inflammation

2020

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Selenium is an essential immunonutrient which holds the human's metabolic activity with its chemical bonds. The organic forms of selenium naturally present in human body are selenocysteine and selenoproteins. These forms have a unique way of synthesis and translational coding. Selenoproteins act as antioxidant warriors for thyroid regulation, male-fertility enhancement, and anti-inflammatory actions. They also participate indirectly in the mechanism of wound healing as oxidative stress reducers. Glutathione peroxidase (GPX) is the major selenoprotein present in the human body, which assists in the control of excessive production of free radical at the site of inflammation. Other than GPX, other selenoproteins include selenoprotein-S that regulates the inflammatory cytokines and selenoprotein-P that serves as an inducer of homeostasis. Previously, reports were mainly focused on the cellular and molecular mechanism of wound healing with reference to various animal models and cell lines. In this review, the role of selenium and its possible routes in translational decoding of selenocysteine, synthesis of selenoproteins, systemic action of selenoproteins and their indirect assimilation in the process of wound healing are explained in detail. Some of the selenium containing compounds which can acts as cancer preventive and therapeutics are also discussed. These compounds directly or indirectly exhibit antioxidant properties which can sustain the intracellular redox status and these activities protect the healthy cells from reactive oxygen species induced oxidative damage. Although the review covers the importance of selenium/selenoproteins in wound healing process, still some unresolved mystery persists which may be resolved in near future.

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Section: Selenocarbonyl Derivativesmentioning

confidence: 99%

Selenium and selenoproteins: it’s role in regulation of inflammation

2020

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“…The reaction between 64 and azides takes place in presence of copper sulfate (hydrated) and sodium ascorbate at room temperature in a mixed solution of polyethylene glycol (PEG) and water (1:1) to result in various derivatives of novel triazolidohydantoins (119) in good yields. 131 The chemical structures of the synthesized compounds were established by IR, 1 H NMR, 13 C NMR, and mass spectral analysis. 132 Further studies to explore the biological applications of these hybrids and modified hybrids are in progress.…”

Section: Hydantoin-triazole Hybrid Moleculesmentioning

confidence: 99%

“…Dimethyl chlorophosphate attacks on the nitrogen to give N-phosphorylated Hydantoins (121) (Scheme 13). 144 The products were characterised by FTIR, 1 H NMR, 13 C NMR, 31 P NMR, and MS data. 145 The XRD studies unequivocally confirmed the formation of N-phosphorylation and ignore the possibility of the formation of O-phosphorylation.…”

Section: Hydantoin-phosphate Hybrid: a Phosphorylated Hydantoinmentioning

confidence: 99%

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Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and its analogs such as thiohydantoin and iminohydantoin have received substantial attention both from a chemical and biological point of view. Several compounds of this class have shown useful pharmacological activities such as anticonvulsant, antitumor, antiarrhythmic, herbicidal, and others that lead in some cases to clinical applications. Because of broad-spectrum activities, intensive research efforts have been dedicated in industry and academia to the synthesis and structural modifications of hydantoin and its derivatives. Realizing the importance of hydantoin in organic and medicinal chemistry, we also initiated a research program to successfully design and develop the new routes/methods resulting in the formation of hydantoin, thiohydantoin, and iminohydantoin substituted at different positions particularly at the N-1 position without following protection-deprotection strategy. Given the fact that the combination of two or more pharmacophoric groups may lead to hybrid molecules which result in a mixed mechanism of action on the biological target. We, therefore, further extended the developed strategy for the synthesis of new types of hydantoin-based hybrid molecules by combining hydantoin with a triazole, isoxazoline, and phosphate scaffolds as another pharmacophoric group to exploit diverse biological functions.

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“…Our findings were in accordance with previous reports. [23,28,29] The successful synthesis of compounds 1 s-4 s was also assured through their mass spectra (ESI-MS) which is not HRMS but sufficiently produce evidence (Automated instrumental mass resolution 0.7 Da) for confirmation of molecules. The ESI-MS spectra were acquired in two separate ionization modes (negative and possitive) that produced prominent molecular ion peak and fragmentation peak which corresponds to theoretical mass acquired from chemdraw ultra 12.0.…”

Section: Spectroscopic Studymentioning

confidence: 99%

Bioactivity and DNA/BSA Interactions of Selenium N‐Heterocyclic Carbene Adducts

et al. 2020

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In wake of promising biomedical applications of organo‐selenium compounds, the present work was planned to synthesize selenium adducts (1 s‐‐4 s) and their respective azolium ligands (1 a–4 a), which were subsequently authenticated by various analytical and spectroscopic techniques like microanalysis, UV‐Visible, FT‐IR, 1H & 13C NMR and Electrospray Ionisation‐Mass Spectrometry (ESI‐MS). Moreover, the synthesized compounds were tested for their biological potential like antioxidant, antimicrobial, hemolytic, DNA and Bovin Serum Albumin (BSA) interactions, stability and lipophilicity using in‐vitro models. All the compounds were found stable in solution form for studied period 12–68 hours and showed good lipophilic values in the range of logP 0.66–0.85. In context to biological activities, selenium compounds showed better antimicrobial (ranging 17.4±0.5–25.3±0.8 mm against S. aureus and 18.6±0.7–24.1±0.9 against E.coli at concentration of 0.3 mg/mL for both strains) and antioxidant potential (IC50 ranging 40.0–62.0 μg/mL for DPPH solutions) compared to respective ligands. The interaction study of compounds (1 s–4 s) to DNA and BSA showed prominent binding affinity.

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Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives

Cited by 28 publications

References 36 publications

Selenium and selenoproteins: it’s role in regulation of inflammation

Selenium and selenoproteins: it’s role in regulation of inflammation

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Bioactivity and DNA/BSA Interactions of Selenium N‐Heterocyclic Carbene Adducts

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