Dmitri LEVITSKY
Professeur émérite Université
août 2024
| Équipe : |
Publications
1 publication
Vil', Vera A; Yaremenko, Ivan A; Fomenkov, Dmitri I; Levitsky, Dmitri O; Fleury, Fabrice; Terent'ev, Alexander O
Ion exchange resin-catalyzed synthesis of bridged tetraoxanes possessing in vitro cytotoxicity against HeLa cancer cells Article de journal
Dans: Chemistry of Heterocyclic Compounds, vol. 56, no. 6, p. 722–726, 2020, ISSN: 1573-8353.
@article{Vil2020,
title = {Ion exchange resin-catalyzed synthesis of bridged tetraoxanes possessing in vitro cytotoxicity against HeLa cancer cells},
author = {Vera A Vil' and Ivan A Yaremenko and Dmitri I Fomenkov and Dmitri O Levitsky and Fabrice Fleury and Alexander O Terent'ev},
url = {https://doi.org/10.1007/s10593-020-02722-4},
doi = {10.1007/s10593-020-02722-4},
issn = {1573-8353},
year = {2020},
date = {2020-01-01},
journal = {Chemistry of Heterocyclic Compounds},
volume = {56},
number = {6},
pages = {722--726},
abstract = {Bridged 1,2,4,5-tetraoxanes were prepared using available acidic ion exchange resin with high yields despite the possibility of peroxide decomposition under heterogeneous conditions. The bridged tetraoxanes demonstrated high cytotoxicity against HeLa cancer cells in vitro, which in some cases was higher than that of cisplatin, artesunate, and dihydroartemisinin.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Bridged 1,2,4,5-tetraoxanes were prepared using available acidic ion exchange resin with high yields despite the possibility of peroxide decomposition under heterogeneous conditions. The bridged tetraoxanes demonstrated high cytotoxicity against HeLa cancer cells in vitro, which in some cases was higher than that of cisplatin, artesunate, and dihydroartemisinin.
2 publications
Yaremenko, Ivan A; Syroeshkin, Mikhail A; Levitsky, Dmitri O; Fleury, Fabrice; Terent'ev, Alexander O
Cyclic peroxides as promising anticancer agents: in vitro cytotoxicity study of synthetic ozonides and tetraoxanes on human prostate cancer cell lines Article de journal
Dans: Medicinal Chemistry Research, vol. 26, no. 1, p. 170–179, 2017, ISSN: 1554-8120.
@article{Yaremenko2017,
title = {Cyclic peroxides as promising anticancer agents: in vitro cytotoxicity study of synthetic ozonides and tetraoxanes on human prostate cancer cell lines},
author = {Ivan A Yaremenko and Mikhail A Syroeshkin and Dmitri O Levitsky and Fabrice Fleury and Alexander O Terent'ev},
url = {https://doi.org/10.1007/s00044-016-1736-2},
doi = {10.1007/s00044-016-1736-2},
issn = {1554-8120},
year = {2017},
date = {2017-01-01},
journal = {Medicinal Chemistry Research},
volume = {26},
number = {1},
pages = {170--179},
abstract = {Synthetic ozonides and tetraoxanes were shown to have high cytotoxicity in vitro when tested on androgen-independent prostate cancer cell lines DU145 and PC3, which is in some cases was higher than that of doxorubicin, cisplatin, etoposide, artemisinin, and artesunate. Activity of ozonide stereoisomers differs from each other. This difference in activity and absence of correlation between activity of stereoisomers and their oxidative properties allow us to suggest existence of a quite specific mechanism of cytotoxicity of these endoperoxides different from a traditional mechanism based mainly on oxidative properties of peroxides.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Synthetic ozonides and tetraoxanes were shown to have high cytotoxicity in vitro when tested on androgen-independent prostate cancer cell lines DU145 and PC3, which is in some cases was higher than that of doxorubicin, cisplatin, etoposide, artemisinin, and artesunate. Activity of ozonide stereoisomers differs from each other. This difference in activity and absence of correlation between activity of stereoisomers and their oxidative properties allow us to suggest existence of a quite specific mechanism of cytotoxicity of these endoperoxides different from a traditional mechanism based mainly on oxidative properties of peroxides.
Levitsky, Dmitri O; Gloriozova, Tatyana A; Poroikov, Vladimir V; Valery, M
ANABOLIC CYANOSTEROIDS AND THEIR BIOLOGICAL ACTIVITIES – A BRIEF REVIEW Article de journal
Dans: vol. 6, no. 12, p. 127–151, 2017, ISBN: 2017121061.
@article{Levitsky2017,
title = {ANABOLIC CYANOSTEROIDS AND THEIR BIOLOGICAL ACTIVITIES – A BRIEF REVIEW},
author = {Dmitri O Levitsky and Tatyana A Gloriozova and Vladimir V Poroikov and M Valery},
doi = {10.20959/wjpps201712-10618},
isbn = {2017121061},
year = {2017},
date = {2017-01-01},
volume = {6},
number = {12},
pages = {127--151},
abstract = {The present review describes the biological activities of synthetic anabolic cyanosteroids. More than forty biologically active compounds have shown confirmed anti-tumour, anti-inflammatory, antiviral and other activities. The structures and reported and predicted activities of synthetic cyanosteroids are available. With the computer programme PASS and based on structure–activity relationships (SAR), some additional activities are also predicted, which point towards new possible applications of these lipids. This review emphasizes the role of cyanosteroids as an important source and potential leads for drug discovery and they are of great interest to chemists, physicians, biologists, pharmacologists and the pharmaceutical industry. KEYWORDS:},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The present review describes the biological activities of synthetic anabolic cyanosteroids. More than forty biologically active compounds have shown confirmed anti-tumour, anti-inflammatory, antiviral and other activities. The structures and reported and predicted activities of synthetic cyanosteroids are available. With the computer programme PASS and based on structure–activity relationships (SAR), some additional activities are also predicted, which point towards new possible applications of these lipids. This review emphasizes the role of cyanosteroids as an important source and potential leads for drug discovery and they are of great interest to chemists, physicians, biologists, pharmacologists and the pharmaceutical industry. KEYWORDS:
4 publications
Krylov, Igor B; Kompanets, Mykhailo O; Novikova, Katerina V; Opeida, Iosip O; Kushch, Olga V; Shelimov, Boris N; Nikishin, Gennady I; Levitsky, Dmitri O; Terent'ev, Alexander O
Well-Known Mediators of Selective Oxidation with Unknown Electronic Structure: Metal-Free Generation and EPR Study of Imide-N-oxyl Radicals Article de journal
Dans: Journal of Physical Chemistry A, vol. 120, no. 1, p. 68–73, 2016, ISSN: 15205215.
@article{Krylov2016,
title = {Well-Known Mediators of Selective Oxidation with Unknown Electronic Structure: Metal-Free Generation and EPR Study of Imide-N-oxyl Radicals},
author = {Igor B Krylov and Mykhailo O Kompanets and Katerina V Novikova and Iosip O Opeida and Olga V Kushch and Boris N Shelimov and Gennady I Nikishin and Dmitri O Levitsky and Alexander O Terent'ev},
doi = {10.1021/acs.jpca.5b10722},
issn = {15205215},
year = {2016},
date = {2016-01-01},
journal = {Journal of Physical Chemistry A},
volume = {120},
number = {1},
pages = {68--73},
abstract = {Nitroxyl radicals are widely used in chemistry, materials sciences, and biology. Imide-N-oxyl radicals are subclass of unique nitroxyl radicals that proved to be useful catalysts and mediators of selective oxidation and CH-functionalization. An efficient metal-free method was developed for the generation of imide-N-oxyl radicals from N-hydroxyimides at room temperature by the reaction with (diacetoxyiodo)benzene. The method allows for the production of high concentrations of free radicals and provides high resolution of their EPR spectra exhibiting the superhyperfine structure from benzene ring protons distant from the radical center. An analysis of the spectra shows that, regardless of the electronic effects of the substituents in the benzene ring, the superhyperfine coupling constant of an unpaired electron with the distant protons at positions 4 and 5 of the aromatic system is substantially greater than that with the protons at positions 3 and 6 that are closer to the N-oxyl radical center. This is indicative of an unusual character of the spin density distribution of the unpaired electron in substituted phthalimide-N-oxyl radicals. Understanding of the nature of the electron density distribution in imide-N-oxyl radicals may be useful for the development of commercial mediators of oxidation based on N-hydroxyimides.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Nitroxyl radicals are widely used in chemistry, materials sciences, and biology. Imide-N-oxyl radicals are subclass of unique nitroxyl radicals that proved to be useful catalysts and mediators of selective oxidation and CH-functionalization. An efficient metal-free method was developed for the generation of imide-N-oxyl radicals from N-hydroxyimides at room temperature by the reaction with (diacetoxyiodo)benzene. The method allows for the production of high concentrations of free radicals and provides high resolution of their EPR spectra exhibiting the superhyperfine structure from benzene ring protons distant from the radical center. An analysis of the spectra shows that, regardless of the electronic effects of the substituents in the benzene ring, the superhyperfine coupling constant of an unpaired electron with the distant protons at positions 4 and 5 of the aromatic system is substantially greater than that with the protons at positions 3 and 6 that are closer to the N-oxyl radical center. This is indicative of an unusual character of the spin density distribution of the unpaired electron in substituted phthalimide-N-oxyl radicals. Understanding of the nature of the electron density distribution in imide-N-oxyl radicals may be useful for the development of commercial mediators of oxidation based on N-hydroxyimides.
Terent'Ev, Alexander O; Pastukhova, Zhanna Yu; Yaremenko, Ivan A; Novikov, Roman A; Demchuk, Dmitry V; Bruk, Lev G; Levitsky, Dmitri O; Fleury, Fabrice; Nikishin, Gennady I
Selective transformation of tricyclic peroxides with pronounced antischistosomal activity into 2-hydroxy-1,5-diketones using iron (II) salts Article de journal
Dans: Tetrahedron, vol. 72, no. 24, p. 3421–3426, 2016, ISSN: 14645416.
@article{TerentEv2016,
title = {Selective transformation of tricyclic peroxides with pronounced antischistosomal activity into 2-hydroxy-1,5-diketones using iron (II) salts},
author = {Alexander O Terent'Ev and Zhanna Yu Pastukhova and Ivan A Yaremenko and Roman A Novikov and Dmitry V Demchuk and Lev G Bruk and Dmitri O Levitsky and Fabrice Fleury and Gennady I Nikishin},
url = {http://dx.doi.org/10.1016/j.tet.2016.04.054},
doi = {10.1016/j.tet.2016.04.054},
issn = {14645416},
year = {2016},
date = {2016-01-01},
journal = {Tetrahedron},
volume = {72},
number = {24},
pages = {3421--3426},
publisher = {Elsevier Ltd},
abstract = {The present work deals with selective transformations of peroxides into organic compounds via the cleavage of the O-O bond using variable valence metals. A selective transformation of tricyclic peroxides promoted by Fe2+ salts was discovered. This selective transformation is unexpected for compounds with structural features which allow diverse decomposition pathways. 2-Hydroxy-1,5-diketones are prepared in yields up to 92% in the reactions of tricyclic peroxides with FeSO4, Fe(ClO4)2, or FeCl2. This is a new preparative method for the synthesis of 1,5-diketones. 2-Hydroxy-1,5-diketones in CDCl3 at 25 °C exist mainly in the open-chain form of the hydroxyketone over the cyclic hemiacetal. The results of this work can be of interest to understand the mechanism of the antiparasitic action of peroxides.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The present work deals with selective transformations of peroxides into organic compounds via the cleavage of the O-O bond using variable valence metals. A selective transformation of tricyclic peroxides promoted by Fe2+ salts was discovered. This selective transformation is unexpected for compounds with structural features which allow diverse decomposition pathways. 2-Hydroxy-1,5-diketones are prepared in yields up to 92% in the reactions of tricyclic peroxides with FeSO4, Fe(ClO4)2, or FeCl2. This is a new preparative method for the synthesis of 1,5-diketones. 2-Hydroxy-1,5-diketones in CDCl3 at 25 °C exist mainly in the open-chain form of the hydroxyketone over the cyclic hemiacetal. The results of this work can be of interest to understand the mechanism of the antiparasitic action of peroxides.
Levitsky, Dmitri O; Gloriozova, Tatyana A; Poroikov, Vladimir V; Dembitsky, Valery M
Mathews Journal of Pharmaceutical Science Naturally Occurring Isocyano / Isothiocyanato Compounds : Their Pharmacological and SAR Activities Article de journal
Dans: MATHEWS, Open Access Journals, vol. 1, no. 1, p. 1–15, 2016.
@article{Levitsky2016,
title = {Mathews Journal of Pharmaceutical Science Naturally Occurring Isocyano / Isothiocyanato Compounds : Their Pharmacological and SAR Activities},
author = {Dmitri O Levitsky and Tatyana A Gloriozova and Vladimir V Poroikov and Valery M Dembitsky},
year = {2016},
date = {2016-01-01},
journal = {MATHEWS, Open Access Journals},
volume = {1},
number = {1},
pages = {1--15},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Zdvizhkov, Alexander T; Terent'Ev, Alexander O; Radulov, Peter S; Novikov, Roman A; Tafeenko, Viktor A; Chernyshev, Vladimir V; Ilovaisky, Alexey I; Levitsky, Dmitri O; Fleury, Fabrice; Nikishin, Gennady I
Transformation of 2-allyl-1,3-diketones to bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings using the I2/H2O2 system Article de journal
Dans: Tetrahedron Letters, vol. 57, no. 8, p. 949–952, 2016, ISSN: 18733581.
@article{Zdvizhkov2016,
title = {Transformation of 2-allyl-1,3-diketones to bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings using the I2/H2O2 system},
author = {Alexander T Zdvizhkov and Alexander O Terent'Ev and Peter S Radulov and Roman A Novikov and Viktor A Tafeenko and Vladimir V Chernyshev and Alexey I Ilovaisky and Dmitri O Levitsky and Fabrice Fleury and Gennady I Nikishin},
url = {http://dx.doi.org/10.1016/j.tetlet.2016.01.061},
doi = {10.1016/j.tetlet.2016.01.061},
issn = {18733581},
year = {2016},
date = {2016-01-01},
journal = {Tetrahedron Letters},
volume = {57},
number = {8},
pages = {949--952},
publisher = {Elsevier Ltd},
abstract = {A one-pot procedure was developed for the assembly of bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings based on the reaction of 2-allyl-1,3-diketones with the I2/H2O2 system. A fivefold molar excess of H2O2 and a twofold excess of I2 are required for the selective formation of tetrahydrofurodioxoles. The synthesis of these structurally complex molecules is unusual in that it does not produce the expected bridged tetraoxanes, products of the addition of several H2O2 molecules to a carbonyl group, or the products of double bond iodoperoxidation.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
A one-pot procedure was developed for the assembly of bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings based on the reaction of 2-allyl-1,3-diketones with the I2/H2O2 system. A fivefold molar excess of H2O2 and a twofold excess of I2 are required for the selective formation of tetrahydrofurodioxoles. The synthesis of these structurally complex molecules is unusual in that it does not produce the expected bridged tetraoxanes, products of the addition of several H2O2 molecules to a carbonyl group, or the products of double bond iodoperoxidation.
1 publication
Terent'ev, Alexander O; Zdvizhkov, Alexander T; Levitsky, Dmitri O; Fleury, Fabrice; Pototskiy, Roman A; Kulakova, Alena N; Nikishin, Gennady I
Organocatalytic peroxidation of malonates, β-ketoesters, and cyanoacetic esters using n-Bu4NI/t-BuOOH-mediated intermolecular oxidative C(sp3)-O coupling Article de journal
Dans: Tetrahedron, vol. 71, no. 47, p. 8985–8990, 2015, ISSN: 14645416.
@article{Terentev2015,
title = {Organocatalytic peroxidation of malonates, β-ketoesters, and cyanoacetic esters using n-Bu4NI/t-BuOOH-mediated intermolecular oxidative C(sp3)-O coupling},
author = {Alexander O Terent'ev and Alexander T Zdvizhkov and Dmitri O Levitsky and Fabrice Fleury and Roman A Pototskiy and Alena N Kulakova and Gennady I Nikishin},
url = {http://dx.doi.org/10.1016/j.tet.2015.09.047},
doi = {10.1016/j.tet.2015.09.047},
issn = {14645416},
year = {2015},
date = {2015-01-01},
journal = {Tetrahedron},
volume = {71},
number = {47},
pages = {8985--8990},
publisher = {Elsevier Ltd},
abstract = {A new organocatalytic approach for the synthesis of peroxides based on CH activation of a sp3-hybridized carbon atom is reported. Peroxides were prepared in 31-89% yield by the reaction of malonates, β-ketoesters, and cyanoacetic esters with a Bu4NI/tert-butyl hydroperoxide system. The formation of the expected hydroxylation products was not observed. In the discovered reaction, tert-butyl hydroperoxide plays a dual role by acting as the oxidant and the O-reagent for the C-O coupling. The synthesis can be scaled up to generate gram quantities of the target products.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
A new organocatalytic approach for the synthesis of peroxides based on CH activation of a sp3-hybridized carbon atom is reported. Peroxides were prepared in 31-89% yield by the reaction of malonates, β-ketoesters, and cyanoacetic esters with a Bu4NI/tert-butyl hydroperoxide system. The formation of the expected hydroxylation products was not observed. In the discovered reaction, tert-butyl hydroperoxide plays a dual role by acting as the oxidant and the O-reagent for the C-O coupling. The synthesis can be scaled up to generate gram quantities of the target products.