- An efficient combined electrochemical and ultrasound assisted synthesis of imidazole-2-thiones
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The electrochemical reduction of 1,3-dialkylimidazolium ionic liquids gave the corresponding N-heterocyclic carbenes that, after reaction with elemental sulfur and ultrasound irradiation, yielded l,3-dialkylimidazole-2-thiones in very high yields. The rea
- Feroci, Marta,Orsini, Monica,Inesi, Achille
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- METHOD FOR ALKYLATING A MOLECULE OR AN ION
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The present invention relates to a method for alkylating a molecule or an ion, wherein the molecule or the ion is alkylated by reacting it with an alkylating agent, wherein the alkylating agent is a compound according to formula (1) or a compound according to formula (4). In the formulae (1) and (4), R1 is a substituted C1-20-alkyl group, an unsubstituted C1-20-alkyl group, a substituted C3-20-cycloalkyl group or an unsubstituted C3-20-cycloaalkyl group, R2 is a substituted or unsubstituted C1-20 hydrocarbon residue or a hydrogen atom, R3 is a substituted or unsubstituted C1-20 hydrocarbon residue or a hydrogen atom, R4 and R5 are linked with each other to form an aromatic group or are independently from each other selected from the group consisting of a hydrogen atom, substituted and unsubstituted C1-20 hydrocarbon residues and electron withdrawing groups, R10 to R13 are independently from each other selected from the group consisting of a hydrogen atom, a substituted C1-20-alkyl group, an unsubstituted C1-20-alkyl group, a substituted C3-20-cycloalkyl group and an unsubstituted C3-20-cycloaalkyl group and A- is an anion.
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Page/Page column 34
(2019/04/16)
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- Chemical Detoxification of Organomercurials
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Organomercurials including methylmercury are ubiquitous environmental pollutants and highly toxic to humans. Now it could be shown that N-methylimidazole based thiones/selones having an N-CH2CH2OH substituent are remarkably effective in detoxifying various organomercurials to produce less toxic HgE (E=S, Se) nanoparticles. Compounds lacking the N-CH2CH2OH substituent failed to produce HgE nanoparticles upon treatment with organomercurials, suggesting that this moiety plays a crucial role in the detoxification by facilitating the desulfurization and deselenization processes. This novel way of detoxifying organomercurials may lead to the discovery of new compounds to treat patients suffering from methylmercury poisoning. Getting rid of mercury: Insoluble HgE (E=S, Se) nanoparticles (NPs) are formed under physiologically relevant conditions when organomercurials are treated with N-methylimidazole-based thiones/selones having an N-CH2CH2OH substituent. Compounds lacking the N-CH2CH2OH substituent failed to produce HgE NPs upon treatment with organomercurials under identical reaction conditions. A novel pathway of detoxifying various organomercurials is described.
- Banerjee, Mainak,Karri, Ramesh,Rawat, Kuber Singh,Muthuvel, Karthick,Pathak, Biswarup,Roy, Gouriprasanna
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p. 9323 - 9327
(2015/08/06)
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- Inhibition of lactoperoxidase-catalyzed oxidation by imidazole-based thiones and selones: A mechanistic study
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Herein, we describe the synthesis and biomimetic activity of a series of N,N-disubstituted thiones and selones that contain an imidazole pharmacophore. The N,N-disubstituted thiones do not show any inhibitory activity towards LPO-catalyzed oxidation reactions, but their corresponding N,N-disubstituted selones exhibit inhibitory activity towards LPO-catalyzed oxidation reactions. Substituents on the N atom of the imidazole ring appear to have a significant effect on the inhibition of LPO-catalyzed oxidation and iodination reactions. Selones 16, 17, and 19, which contain methyl, ethyl, and benzyl substituents, exhibit similar inhibition activities towards LPO-catalyzed oxidation reactions with IC50 values of 24.4, 22.5, and 22.5 μM, respectively. However, their activities are almost three-fold lower than that of the commonly used anti-thyroid drug methimazole (MMI). In contrast, selone 21, which contains a N-CH2CH2OH substituent, exhibits high inhibitory activity, with an IC50 value of 7.2 μM, which is similar to that of MMI. The inhibitory activity of these selones towards LPO-catalyzed oxidation/iodination reactions is due to their ability to decrease the concentrations of the co-substrates (H2O2 and I 2), either by catalytically reducing H2O2 (anti-oxidant activity) or by forming stable charge-transfer complexes with oxidized iodide species. The inhibition of LPO-catalyzed oxidation/iodination reactions by N,N-disubstituted selones can be reversed by increasing the concentration of H2O2. Interestingly, all of the N,N-disubstituted selones exhibit high anti-oxidant activities and their glutathione peroxidase (GPx)-like activity is 4-12-fold higher than that of the well-known GPx-mimic ebselen. These experimental and theoretical studies suggest that the selones exist as zwitterions, in which the imidazole ring contains a positive charge and the selenium atom carries a large negative charge. Therefore, the selenium moieties of these selones possess highly nucleophilic character. The 77Se NMR chemical shifts for the selones show large upfield shift, thus confirming the zwitterionic structure in solution. Stop, in the name of love: The inhibition of lactoperoxidase (LPO)-catalyzed reactions by a series of N,N-disubstituted thiones and selones that contain an imidazole pharmacophore is described. The inhibitory activity not only depends on the substituent that is attached to the nitrogen atom, but also on the nature of the chalcogen atom. The inhibition of LPO activity by selones is due to their ability to scavenge the substrate, hydrogen peroxide. Copyright
- Roy, Gouriprasanna,Jayaram,Mugesh, Govindasamy
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p. 1910 - 1921
(2013/09/02)
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- Unexpected microwave reaction of 1,3-disubstituted imidazolium salts: A novel synthesis of 1,3-disubstituted imidazole-2-thiones
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Microwave-promoted reaction of 1,3-disubstituted imidazolium salts with potassium thioacetate or potassium thiocyanate under solvent-free conditions provided a rapid and efficient synthesis of 1,3-disubstituted imidazole-2-thiones. Copyright Taylor & Francis Group, LLC.
- Tao, Xiao-Le,Lei, Ming,Wang, Yan-Guang
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p. 399 - 408
(2007/10/03)
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- Imidazole compounds and their use as transglutaminase inhibitors
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Imidazole compounds including imidazoles and imidazolium salts, and their use as transglutaminase inhibitors are disclosed.
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- PHOTOCHEMISTRY OF AZOLES, PART VII. PHOTOSOLVOLYSIS OF ALKYLMERCAPTOAZOLES. AN APPLICATION TO SOME ACYCLIC MONOTERPENE DERIVATIVES
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Salts derived from 2-alkylmercapto-1-methylimidazoles 1b-e and 3-alkylmercapto-4-methyl-1,2,4-triazoles 2b-d have been found to undergo photochemical heterolytic fission of the S-alkyl bond in aqueous or methanolic solution to give solvolysis-type products.
- Iwasaki, Shigeo
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p. 125 - 138
(2007/10/02)
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