Microwave-assisted preparation, structural characterization, lipophilicity, and anti-cancer assay of some hydroxycoumarin derivatives

Ostrowska, Kinga; Hejchman, Elżbieta; Maciejewska, Dorota; Włodarczyk, Agata; Wojnicki, Kamil; Matosiuk, Dariusz; Czajkowska, Agnieszka; Młynarczuk-Biały, Izabela

doi:10.1007/s00706-014-1320-8

Cited by 11 publications

(3 citation statements)

References 23 publications

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“…Another suggestion was that the addition of acetyl moiety to O-alkyl derivatives of 4methylumbelliferone may enhance their antitumor effect. It was recommended that other studies are required to highlight the effect of the lipophilicity on the anticancer attribute of 4-methylumbelliferonebased compounds [40]. Fig.…”

Section: Introductionmentioning

confidence: 99%

4-Methylumbelliferone And Its Derived Compounds: A Brief Review Of Their Cytotoxicity

2021

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Many efforts have been directed toward the isolation of natural products, and using them to synthesize new chemical agents, and explore their cytotoxic attributes. However, finding new chemotherapeutic agents with towering potentials in the terms of high activity and target-selectivity, as well as minimal side effects is still out of hand. To satisfy that, medicinal chemists directed much of their research toward screening the cytotoxic activity of the isolated products and synthetic compounds. One of the most investigated bands of compounds is those belong to coumarin-family. Although most of these family members exhibited characteristic cytotoxic attributes, the compound termed 4-methylumbelliferone and chemically named 7-hydroxy-4-methylcoumarin showed, with its derived compounds, an exceptional activity in cancer therapy. This effect included the ability of these compounds to counteract the mechanisms of the multidrug-tumor resistance, cover the side potentials of the currently used chemotherapeutic drugs, and boost the tumor sensitivity to phototherapy. In this report, we browsed the literature to report the recent advances for the application of 4-methylumbelliferone and its derived compounds as cytotoxic agents and identify the structural requirements for the maximum selectivity versus each cancer-phenotype. The outcomes of this report may help in the direction of research toward designing and synthesizing new 4-methylumbelliferone-derived products exhibiting the best selectivity and green-side potentials.

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Section: Introductionmentioning

confidence: 99%

4-Methylumbelliferone And Its Derived Compounds: A Brief Review Of Their Cytotoxicity

2021

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“…Each step reaction must be carried out under anhydrous conditions and supplemented with appropriate catalysts. In the final step of condensation reaction, if we use the phase transfer method, the reaction rate is fast, the unit productivity is high and the cost is relatively low [5][6][7][8]. Because of the reaction occurring at the interface between water phase and oil phase, O, O-diethyl thiophosphoryl chloride will be consumed due to hydrolysis, resulting in low yield and the purity of product is also reduced by mixing with some impurities.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of Diazinon with The Catalysis of Ionic Liquid under The Condition of Microwave

Hu¹,

Wang²,

Zhou³

et al. 2017

Proceedings of the 2016 International Conference on Biological Engineering and Pharmacy (BEP 2016)

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Abstract-A novel synthetic methods for the efficient and environmentally-friendly production will provide useful inspiration. This report presents a novel method for microwave-assisted synthesis of diazinon with different organic solvents, microwave heating power, heating time, catalysts. The optimal conditions for this synthesis are: 750W for microwave power, 12 min. for heating time, and 0.02% for mole ratio of catalyst DMAP to O, O-diethyl thiophosphoryl chloride and 1, 2-dichloroethane for the best solvent, which can lead the yield of diazinon to 67.86%. When adding repeatedly fresh 2-isopropyl-6-methyl-4-hydroxy pyrimidine for enough times, the yield of diazinon for O, O-diethyl phosphoryl chloride can be as high as 86.54%. With an amazing chemical reaction rate and less waste water discharge, microwaveassisted synthesis is a promising method for green synthesis.

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“…In order to provide tool compounds for the ongoing scientific efforts to further characterize the biological activity of ebselen, we designed two activity-based probes containing the intact ebselen structure and a rigidified 7-amino coumarin (coumarin 343) as the fluorescent tag. Coumarins represent a widely used type of fluorophores and are characterized by their small molecular size, large Stokes shifts as well as chemical and enzymatic stability [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ]. In the second heterodimer, the coumarin tag should be connected via a PEG/two-amide linker with the ebselen substructure ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Convergent Synthesis of Two Fluorescent Ebselen-Coumarin Heterodimers

et al. 2016

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The organo-seleniumdrug ebselen exhibits a wide range of pharmacological effects that are predominantly due to its interference with redox systems catalyzed by seleno enzymes, e.g., glutathione peroxidase and thioredoxin reductase. Moreover, ebselen can covalently interact with thiol groups of several enzymes. According to its pleiotropic mode of action, ebselen has been investigated in clinical trials for the prevention and treatment of different ailments. Fluorescence-labeled probes containing ebselen are expected to be suitable for further biological and medicinal studies. We therefore designed and synthesized two coumarin-tagged activity-based probes bearing the ebselen warhead. The heterodimers differ by the nature of the spacer structure, for which—in the second compound—a PEG/two-amide spacer was introduced. The interaction of this probe and of ebselen with two cysteine proteases was investigated.

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Microwave-assisted preparation, structural characterization, lipophilicity, and anti-cancer assay of some hydroxycoumarin derivatives

Cited by 11 publications

References 23 publications

4-Methylumbelliferone And Its Derived Compounds: A Brief Review Of Their Cytotoxicity

4-Methylumbelliferone And Its Derived Compounds: A Brief Review Of Their Cytotoxicity

The Synthesis of Diazinon with The Catalysis of Ionic Liquid under The Condition of Microwave

Convergent Synthesis of Two Fluorescent Ebselen-Coumarin Heterodimers

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