A5051601607- Oxidative Organic Chemistry Reactions
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Chemical Synthesis and Reactions
- Synthesis and Catalytic Reactions
- Chemical Reactions and Mechanisms
- Asymmetric Synthesis and Catalysis
- Synthesis and biological activity
- Malaria Research and Control
- Synthesis and Biological Evaluation
- Computational Drug Discovery Methods
- Radical Photochemical Reactions
- Electrochemical sensors and biosensors
- Conducting polymers and applications
- Inorganic and Organometallic Chemistry
- Organic Chemistry Cycloaddition Reactions
- Vanadium and Halogenation Chemistry
- Chemical Reaction Mechanisms
- Parasites and Host Interactions
- Chemical Synthesis and Analysis
- Electrochemical Analysis and Applications
- Synthetic Organic Chemistry Methods
- Research on Leishmaniasis Studies
- Fungal Plant Pathogen Control
- Catalytic C–H Functionalization Methods
N.D. Zelinsky Institute of Organic Chemistry
2016-2025
Royal Society of Chemistry
2024
Centre National pour la Recherche Scientifique et Technique (CNRST)
2024
D. Mendeleyev University of Chemical Technology of Russia
2017-2023
Russian Research Institute for Phytopathology
2017-2022
Russian Academy of Sciences
2012-2018
Lomonosov Moscow State University
2015
The chemistry of heterocyclic compounds has traditionally been and remains a bright area chemical science in Russia. This is due to the fact that many heterocycles find widest application. These are key structural fragments most drugs, plant protection agents. Many natural also derivatives heterocycles. At present, more than half hundreds millions known collective review devoted achievements Russian chemists this field over last 15–20 years. presents leading heterocyclists representing both...
Although antischistosomal properties of peroxides were studied in recent years, systematic structure-activity relationships have not been conducted. We evaluated the potential 64 belonging to bridged 1,2,4,5-tetraoxanes, alphaperoxides, and tricyclic monoperoxides. Thirty-nine compounds presented IC₅₀ values <15 μM on newly transformed schistosomula. Active drugs featured phenyl-, adamantane-, or alkyl residues at methylene bridge. Lower susceptibility was documented adult schistosomes, with...
A photocatalytic three-component sulfonyl peroxidation of alkenes with N-sulfonyl ketimines and tert-butyl hydroperoxide is reported. The reaction takes place via the photoinduced EnT process, which allows efficient synthesis a variety β-peroxyl sulfones under mild conditions in absence transition metal catalyst. downstream derivatizations peroxides were also performed. Furthermore, utility this protocol was manifested by 11β-HSD1 inhibitor antiprostate cancer drug bicalutamide.
Abstract Twenty six peroxides belonging to bridged 1,2,4,5‐tetraoxanes, 1,2,4‐trioxolanes (ozonides), and tricyclic monoperoxides were evaluated for their in vitro antimalarial activity against Plasmodium falciparum (3D7) cytotoxic activities immortalized human normal fibroblast (CCD19Lu), liver (LO 2 ), lung (BEAS‐2B) cell lines as well (HepG2) (A549) cancer‐cell lines. Synthetic ozonides shown have the highest cytotoxicity on HepG2 (IC 50 =0.19–0.59 μ m some of these compounds selectively...
Abstract The value of stereoelectronic guidelines is illustrated by the discovery a convenient, ozone‐free synthesis bridged secondary ozonides from 1,5‐dicarbonyl compounds and H 2 O . tetraoxane products generally formed in reactions carbonyl dicarbonyl with were not detected because structural distortions imposed on tetraoxacyclohexane subunit [3.2.2]tetraoxanonanes three‐carbon bridge leads to partial deactivation anomeric effects. new procedure readily scalable produce gram quantities...
Reactions of 1,5-diketones with H2O2 open an ozone-free approach to ozonides. Bridged ozonides are formed readily at room temperature in the presence strong Brønsted or Lewis acids such as H2SO4, p-TsOH, HBF4, BF3·Et2O. The expected bridged tetraoxanes, products double addition, were not detected. This procedure is scalable produce gram quantities stable and can be useful building blocks for bioconjugation further synthetic transformations. Although less stabilized by anomeric interactions...
The newly emerged severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) cause life-threatening diseases in millions of people worldwide, particular, patients with cancer, and there is an urgent need for antiviral agents against this infection. While vitro activities artemisinins SARS-CoV-2 cancer have recently been demonstrated, no study artemisinin and/or synthetic peroxide-based hybrid compounds active both has reported yet. However, the drug's properties (e. g., activity...
Stable tricyclic aminoperoxides can be selectively assembled via a catalyst-free three-component condensation of β,δ'-triketones, H2O2, and an NH-group source such as aqueous ammonia or ammonium salts. This procedure is scalable produce gram quantities heterocycles, containing peroxide, nitrogen, oxygen cycles in one molecule. Amazingly, complex molecules are formed despite the multitude alternative reaction routes, equilibration hemiaminal, monoperoxyacetal, peroxyhemiaminal...
The transition metal (Cu, Fe, Mn, Co) catalyzed peroxidation of β-dicarbonyl compounds at the α position by tert-butyl hydroperoxide was discovered. A selective, experimentally convenient, and gram-scale method developed for synthesis α-peroxidated derivatives β-diketones, β-keto esters, diethyl malonate. Virtually stoichiometric (2−3/1) molar ratios a dicarbonyl compound were used in reactions with β-diketones esters. target synthesized highest yields from esters (45−90%) somewhat lower...
The catalyst H3+x PMo12-x+6 Mox+5 O40 supported on SiO2 was developed for peroxidation of 1,3- and 1,5-diketones with hydrogen peroxide the formation bridged 1,2,4,5-tetraoxanes 1,2,4-trioxolanes (ozonides) high yield based isolated products (up to 86 90 %, respectively) under heterogeneous conditions. Synthesis peroxides conditions is a rare process represents challenge this field chemistry, because tend decompose surface . A new class antifungal agents crop protection, that is, cyclic...
This article discloses a new horizon for the application of peroxides in medical chemistry. Stable cyclic are demonstrated to have cytotoxic activity against cancer cells; addition mechanism action is proposed. Synthetic bridged 1,2,4,5-tetraoxanes and ozonides were effective HepG2 cells some selectively targeted liver (the selectivity indexes compounds 11 b 12 8 5, respectively). In cases, tetraoxanes more selective than paclitaxel, artemisinin, artesunic acid. Annexin V flow-cytometry...
A method for the assembly of tricyclic structures containing peroxide, monoperoxyacetal, and acetal moieties was developed based on acid-catalyzed reaction β,δ-triketones with H(2)O(2). Tricyclic compounds are formed selectively in yields from 39% to 90% by reactions use large amounts strong acids, such as H(2)SO(4), HClO(4), or HBF(4), which act both catalyst co-solvent. The is unusual that, despite diversity possible peroxidation pathways giving cyclic oligomers, proceeds high selectivity...
Phosphomolybdic acid (PMA) and phosphotungstic (PTA) efficiently catalyze the addition of H2O2 to β-diketones form bridged 1,2,4,5-tetraoxanes. These reactions are not accompanied by formation monocyclic peroxides containing hydroxy hydroperoxide groups or polymeric peroxides. The use these catalysts made it possible obtain tetraoxanes from easily oxidizable benzoylacetone derivatives α-unsubstituted β-diketones. syntheses scaled up ten grams. resulting can be isolated reaction mixture...
In recent years, the number of pollinators in world has significantly decreased. A possible reason for this is toxic effects agrochemicals reducing immunity insects that leads to their increased susceptibility pathogens. Ascosphaera apis a dangerous entomopathogenic fungus, afflicting both honeybees and bumblebees. We investigated fungicide activity cyclic synthetic peroxides against A. isolated from Bombus terrestris L. The exhibited high mycelium growth inhibition up 94–100% at...
Stable bridged azaozonides can be selectively assembled via a catalyst-free three-component condensation of 1,5-diketones, hydrogen peroxide, and an NH-group source such as aqueous ammonia or ammonium salts. This procedure is scalable produce gram quantities bicyclic stereochemically rich heterocycles. The new are thermally stable stored at room temperature for several months without decomposition least 1 year −10 °C. chemical stability was explored their subsequent selective transformations...
Bridged aminoperoxides, for the first time, were investigated in vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum strain K1 and their cytotoxic activities immortalized human normal liver (LO2) lung (BEAS-2B) cell lines as well (HepG2) (A549) cancer lines. Aminoperoxides exhibit good cytotoxicity A549 line. Synthetic ozonides shown to have high P. falciparum. A cyclic voltammetry study of peroxides was performed, most compounds did not show a direct correlation...
Four heteroatoms dance in the cascade of four pericyclic reactions initiated by ozonolysis C═N bonds. Switching from imines to semicarbazones introduces fifth heteroatom that slows this dance, delays reaching thermodynamically favorable escape path, and allows efficient interception carbonyl oxides (Criegee intermediates, CIs) an external nucleophile. The new three-component reaction alcohols, ozone, oximes/semicarbazones greatly facilitates synthetic access monoperoxyacetals (alkoxyhydroperoxides).
Ozonolysis of cycloalkanone semicarbazones in alcohol containing solution with the subsequent addition nickel (II) dithiocarbamates or xanthates was found to result ω‐xanthyl ω‐dithiocarbamyl carboxylic acid esters. The reaction proceeds several steps. initial one is semicarbazone ozonolysis presence alcohol, which leads alicyclic alkoxyhydroperoxide. second step an extraordinary interaction between alkoxyhydroperoxide and dithiocarbamate xanthate, via alkoxy radical formation its...
Forty‐five aminoperoxides belonging to bridged azaozonides, N‐substituted and tricyclic were evaluated for in vitro antimalarial activity against Plasmodium falciparum (3D7) cytotoxicity immortalized human normal liver (LO2) lung (BEAS‐2B) cell lines, as well (HepG2) (A549) cancer lines. Seven azaozonides exhibited high the chloroquine‐sensitive 3D7 strain of P. falciparum, with IC50 < 1 µM. The lead compound 22 showed = 0.07 µM selectivity index 1428. Most generally non‐cytotoxic both...