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2011 year, number 6

1.
New Approaches to the Development of Biologically Active Water-Soluble Antioxidants

N. V. KANDALINTSEVA,Y. N. TRUBNIKOVA and A. E. PROSENKO
Research Institute of Antioxidant Chemistry, Novosibirsk State Pedagogical University,
Ul. Vilyuyskaya 28, Novosibirsk 630126 (Russia)
aquaphenol@mail.ru
Keywords: phenols, polyfunctional phenolic antioxidants, water-soluble antioxidants, antioxidant activity, free radical pathologies
Pages: 545555

Abstract >>
Results obtained by the authors in the investigations in the area of synthesis and examination of the antioxidant properties of polyfunctional water-soluble antioxidants based on alkylated phenols are presented in the review. The promising character of the use of synthesized compounds for corrections of pathological states connected with the development of oxidative stress is demonstrated.

UDC 543.544+615:322



2.
The Use of Chromatographic Profiling Methods for Analyzing and Identifying Low Molecular Mass Organic Substances of Natural and Anthropogenic Origin

S. V. MOROZOVand E. I. CHERNYAK
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Pr. Akademika Lavrentyeva 9, Novosibirsk 630090 (Russia)
moroz@nioch.nsc.ru
Keywords: chromatographic profiles, spectral characteristics, gas chromatography-mass spectrometry, low molecular mass biologically active substances, persistent organic pollutants, environmental chemistry, chemistry of natural compounds, living systems
Pages: 557573

Abstract >>
An approach for the determination of the individual and the group composition for low molecular mass organic substances of natural and anthropogenic origin basing on the analysis of chromatographic profiles (“fingerprints”) and the spectral characteristics. Data are presented concerning the use of the approach for the identification of persistent organic pollutants in the environment of Siberia and Mongolia with the purpose of assessing the risk of the chemical compounds to affect human health and ecosystems, as well as of identifying the main sources of pollution. There are potentialities considered concerning the approach for the analysis of biologically active substances of plant or animal origin, the development of low-dose preparations for agriculture biomass based on Siberian coniferous plants as well as the studies of living systems. It is demonstrated that chromatographic profiles represent highly informative characteristics those could be used in order to recognize a chemical image of complex systems, to identify and predict properties inherent in these objects.

UDC 547.931.2



3.
Terpenes in Superacids: Synthetic Aspect

M. P. POLOVINKA and N. F. SALAKHYTDINOV
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Pr. Akademika Lavrentyeva 9, Novosibirsk 630090 (Russia)
polovina@nioch.nsc.ru
Keywords: super-acids, terpenoids, cationoid rearrangements, selectivity
Pages: 575588

Abstract >>
Possibilities to use superacids for the synthesis of optically active natural compounds are analyzed in the review. The revealed regularities of cationoid rearrangements of terpenoids under the conditions of super-nucleophilic media and low temperatures are taken into account. Mono- and sesquiditerpenoids and their analogs are chosen as the subject of investigation. Results of works published since 1984 till 2004, including those supervised by Prof. V. A. Koptyug, are reviewed.

UDC 547.548



4.
Novel Method for the Bromination of Aromatic Polynitro ompounds

A. M. ANDRIEVSKIY
Research Institute of Organic Intermediate Products and Dyes,
Ul. B. Sadovaya 1/4, Moscow 123995 (Russia)
ShebanGV@yandex.ru
Keywords: bromination, aromatic compounds, dinitrobenzenes, bromine, nitric acid
Pages: 589592

Abstract >>
A simple method of bromination with a high yield is proposed for severely deactivated aromatic compounds, such as 1,3-dinitrobenzenes and polycyclic nitro compounds. The method proposed is based on the action of bromine in sulphuric acid in the presence of nitric acid. The reaction stoichiometry corresponds to the consumption of 0.5 mol of bromine and 0.5 mol of nitric acid per 1 mol of an aromatic substrate. The nature of the bromination agent is under discussion.

UDC 547.551.4+547.56+547.655.1+547.831.4



5.
Eco-Friendly Fluorination of Aromatic Compounds with F-TEDA-BF4 Reagent in Water

G. I. BORODKIN,P. A. ZAIKINandV. G. SHUBIN
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Pr. Akademika Lavrentyeva 9, Novosibirsk 630090 (Russia)
gibor@nioch.nsc.ru
Keywords: NF reagent, electrophilic fluorination, selectivity, eco-friendly solvents, water, phenols, acetanilide and heteroaromatic compounds
Pages: 593598

Abstract >>
The interaction of bis(tetrafluoroborate) of 1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane (F-TEDA-BF4) with phenol, acetanilide and their derivatives, resorcinol, 1-, 2-naphthols and 6-methoxyquinoline in water was investigated. In some cases, fluorination of aromatic compounds in water proceeds more selectively than in the case when organic solvents are used.

UDC 544.164.032.6



6.
Photochromism of 6′-Cyano-Substituted Spironaphthooxazines in the Solid Phase

E. M. GLEBOV1,2, A. B. SMOLENTSEV1, V. V. KOROLEV1,2, V. F. PLYUSNIN1,2, A. V. METELITSA3, N. A. VOLOSHIN3 and V. I. MINKIN3
1 Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences,
Ul. Institutskaya 3, Novosibirsk 630090 (Russia)
glebov@kinetics.nsc.ru
2 Novosibirsk State University,
Ul. Pirogova 2, Novosibirsk 630090 (Russia)
3Research Institute of Physical and Organic Chemistry, Southern Federal University,
Pr. Stachki 194/2, Rostov-na-Donu 344104 (Russia)
Keywords: photochemistry, photochromism, quantum yield, spirooxazines, polycrystalline films
Pages: 599603

Abstract >>
For three 6′-cyano-substituted spironaphthooxazines (SNO), photochromic properties were revealed in the films obtained from melts. Quantum yields were determined for the forward and reverse photochemical reactions. Unlike phenanthroline-containing spirooxazines, SNO polycrystals do not exhibit photochromic properties.

UDC 544-16; 615,31



7.
Interaction of Glycyrrhizic Acid with the Products of Cholesterol Oxidation: a New View of the Problem of Atherosclerosis

O. YU. GLUSHCHENKO,N. E. POLYAKOV and T. V. LESHINA
Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences,
Ul. Institutskaya 3, Novosibirsk 630090 (Russia)
olga.gluschenko@gmail.com
Keywords: cholesterol oxidation, ozone, glycyrrhizic acid, atherosclerosis, cholesterol complex
Pages: 605609

Abstract >>
The ability of glycyrrhizic acid to form complexes with the products of cholesterol oxidation was studied. The effect of complexing on the rate of cholesterol oxidation with ozone was studied. It was shown that the formation of complex with glycyrrhizic acid may become an efficient approach to govern the level of cholesterol inside and outside of cell membranes, and to extract the products of cholesterol oxidation.

UDC 542.61:547.913



8.
Triterpenoids Inherent in the Coniferous Plants of Pinaceae Family

T. P. KUKINA and E. N. SHMIDT
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Pr. Akademika Lavrentyeva 9, Novosibirsk 630090 (Russia)
kukina@nioch.nsc.ru
Keywords: triterpenoids, Pinaceae family, lanostanoids, serratanes
Pages: 611615

Abstract >>
An attempt is made to systematize the data from scientific publications, patents and the internet resources concerning triterpene components in the plants of Pinaceae family those could be considered as chemotaxonomic markers and as the active principle of biologically active preparations. Examples are given for the major structural groups of triterpenoids inherent in conifers and data concerning the presence of these compounds in total extractive substances of the plants of different genera of the family. A problem connected with the examination of bioactivity of triterpenoids inherent in coniferous plants is assessed.

UDC 541.64:541.68+546.171.1+547.539.1



9.
Polyimides of AA/BB and AB Types Based on New Perfluorinated Monomers

E. V. MALYKHIN, T. A. VAGANOVA, I. K. SHUNDRINA, S. Z. KUSOV, V. I. RODIONOV and E. V. KARPOVA
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Pr. Akademika Lavrentyeva 9, Novosibirsk 630090 (Russia)
malykhin@nioch.nsc.ru
Keywords: polyfluoroarylenediamines, polyfluorohetarylenediamines, aminodefluorination, liquid ammonia, synthesis of fluoroaromatic polyimides, thermal stability, optical transparency
Pages: 617624

Abstract >>
Convenient methods of the synthesis of new perfluoroaromatic monomers of BB and AB types and polyimides on their basis were developed. The effect of the structural factors (the nature of aromatic framework, substituents and bridges, isomerism) on the reactivity of monomers and major characteristics of polyimides was discussed. It was established that the obtained polyimides possess promising properties for optoelectronic applications.

UDC 544.546



10.
Features of Chemical Reactions in the Absence of Solvents under Microwave Action

A. N. MIKHEEV,V. G. MAKOTCHENKO, N. A. PANKRUSHINA, M. O. KOROTKIKH, A. V. ARZHANNIKOV and M. K. A THUMM
Novosibirsk State University,
Ul. Pirogova 2, Novosibirsk 630090 (Russia)
man@niic.nsc.ru
Keywords: microwave chemistry, microwave heating, intercalation compounds, dicarbon polyfluoride, solvent-free reactions
Pages: 625632

Abstract >>
Features of a number of chemical reactions in the absence of solvents under microwave action were investigated. The features of microwave heating of phthalic anhydride and glycine before and after melting were studied. It was shown that the microwave synthesis of glycine phthalimide occurs efficiently and with the high yield in the reaction mixture heated above the melting point of phthalic anhydride. Decomposition of intercalation compounds of chlorine trifluoride and intercalation compounds with acetone, acetonitrile, benzene and carbon tetrachloride implanted into the interlayer space of dicarbon polyfluoride was investigated. It was shown that the decomposition of intercalation compounds under microwave heating resulting in the formation of nanostructured graphite occurs at lower temperature values than those involved in conventional convection heating. It was concluded on the basis of experimental results that the absorption of microwave energy is connected with the dielectric properties of the substances intercalated into the interlayer space of dicarbon polyfluoride matrix. Experiments were carried out with Explorer-48 set-up with the microwave unit Discover S-class (CEM Corporation, the USA) operating at the frequency of 2450 MHz under the conditions of controlled power of microwave action within the range 0–300 W.

UDC 547.92+547.926.5+542.91+542.941



11.
Molecular Rearrangements under Chemical Transformations of Ecdysteroids

V. N. ODINOKOV
Institute of Petrochemistry and Catalysis, Ufa Scientific Centre of the Russian Academy of Sciences,
Pr. Oktyabrya 141, Ufa 450075 (Russia)
odinokov@anrb.ru
Keywords: ecdysteroids, 9α,14α-epoxy-14α-desoxyecdysteroids, molecular rearrangements, 9α,13α-epoxy-14β-methyl-13β-demethyl-14α-desoxyecdysteroids, hydride reduction, catalytic hydrogenation
Pages: 633638

Abstract >>
It was established that 9α,14α-epoxy-14α-desoxyecdysteroids (oxetanoecdysteroids) formed from the corresponding ecdysteroids in the solutions of alkaline metals in liquid ammonia undergo molecular rearrangements catalyzed by acids. As a result of these rearrangements, 9α,13α-epoxy-14β-methyl-13β-demethyl-14α-desoxyecdysteroids and 9α-hydroxystachisteron are formed. The reduction of oxetanoecdysteroids by sodium borohydride results not only in the reduction of 6-keto group but also in the rearrangement of the oxetane cycle. The oxetane molecular rearrangement also takes place during catalytic hdyration of Δ7-bond in oxetanoecdysteroids.

UDC 547+544



12.
Synthesis and Antioxidant Properties of ω-[3-(4-Hydroxyaryl)propylthio]alkanic Acids

Y. N. TRUBNIKOVA1, S. E. YAGUNOV1, N. A. GAAS1, A. S. OLEYNIK1, N. V. KANDALINTSEVA1,2 and A. E. PROSENKO1,2
1 Research Institute of Antioxidant Chemistry, Novosibirsk State Pedagogical University,
Ul. Vilyuyskaya 28, Novosibirsk 630126 (Russia)
chemistry@ngs.ru
2 Novosibirsk Institute of Antioxidants,
Ul. Vilyuyskaya 28, Novosibirsk 630126 (Russia)
Keywords: phenols, polyfunctional antioxidants, thioalkanoic acids, phenosan, antioxidant activity
Pages: 639645

Abstract >>
On the basis of bromopropyl-, mercaptopropyl- and allyl-substituted phenols, the synthesis of ω-[3-(4-hydroxyaryl)propylthio]alkalic acids was carried out. It was shown in the model reaction of methyl oleate autooxidation that the synthesized ω-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylthio]alkanoic acids exceed phenosan antioxidant in the antioxidant activity due to the presence of sulphide groups in their structure.

UDC 547.567+543.272.75+547.362+66.095.252+547.77+547.852.7



13.
Mechanism and Synthesis Potentialities of the Cyclization of vic-(Alkynyl)arenediazonium Salts

L. G. FEDENOK,I. I. BARABANOV,N. A. ZOLNIKOVA,V. S. BASHUROVA andG. A. BOGDANCHIKOV
Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences,
Ul. Institutskaya 3, Novosibirsk 630090 (Russia)
fedenok@kinetics.nsc.ru
Keywords: cyclization, mechanism, vic-(alkynyl)arenediazonium salts, Richter reaction, indazoles, cinnolines
Pages: 647651

Abstract >>
Cyclization of vic-alkynyl-substituted diazonium salts in the series of anthraquinone, naphthoquinone and benzene was studied. Basing on experimental data and the results of quantum chemical calculations, a scheme of heterocyclization mechanism was proposed for vic-(alkynyl)arenediazonium salts. The scheme proposed is fundamentally different from the generally accepted scheme of the Richter reaction mechanism.

UDC 621.926.47



14.
Mechanochemical Modification of the Properties of Antihelminthic Preparations

S. S. KHALIKOV1, M. S. KHALIKOV1, E. S. METELEVA2, S. A. GUSKOV2, V. I. EVSEENKO2, A. V. DUSHKIN2, V. S. BURANBAEV3, R. G. FAZLAEV4, V. Z. GALIMOVA4 and A. M. GALIULLINA4
1 Research Technological Institute of Herbicides and Plant Growth Regulators with Experimental Production, Academy of Sciences of the Republic of Bashkortostan,
Ul. Ulyanovykh 65, Ufa 450029 (Russia)
salavatkhalikov@mail.ru
2 Institute of Solid State Chemistry and Mechanochemistry, Siberian Branch of the Russian Academy of Sciences,
Ul. Kutateladze 18, Novosibirsk 6300128 (Russia)
3 Republic of Bashkortostan, Department of Veterinary,
Ul. Pushkina 106, Ufa 450001 (Russia)
4 Bashkir State Agricultural University,
Ul. 50 Let Oktyabrya 34, Ufa 450001 (Russia)
Keywords: antihelminthic preparations, carbendacim, albendazole, polymers, polysaccharides, grinding, mechanical activation, supramolecular complexes water solubility, particle size, nanotechnology, mechanochemical synthesis, echinococcosis
Pages: 653657

Abstract >>
The processes of joint mechanical activation of some benzimidazole antihelminthic preparations with water-soluble polymers in the mills of shock-attrition type were studied. The conditions of synthesis of supramolecular complexes with different components ratios and energy strain of activator mills were discussed. The products of mechanochemical synthesis were characterized on the basis of water solubility and particle size. The products obtained possess higher water solubility and smaller particle size than the initial benzimidazole compounds; the products are of interest as potential antihelminthic preparations with increased efficiency.

UDC 544.52+544.526.2+547.32



15.
Photochemistry of Herbicide 2,4,5-Trichlorophenoxyacetic Acid in Aqueous Solutions in the Presence of Cyclodextrins

M. P. YURKOVA, I. P. POZDNYAKOV, V. P. GRIVINandV. F. PLYUSNIN
Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences,
Ul. Institutskaya 3, Novosibirsk 630090 (Russia)
yurkova@kinetics.nsc.ru
Keywords: photochemistry, photodegradation, herbicides, photoionization, hydrated electron, laser flash photolysis, cyclodextrins, inclusion complexes
Pages: 659664

Abstract >>
Photodegradation of herbicide 2,4,5-trichlorophenoxyacetic acid (2,4,5-) in aqueous solutions was studied by means of steady-state and nanosecond laser flash photolysis. It was demonstrated that the primary photochemical act involves one- and two-photon ionization of the herbicide and the formation of the hydrated electron/radical cation pair. In oxygen-free solutions, hydrated electron disappears due to capturing by the initial compound, whereas the radical cation gets hydrolyzed with water to form a long-living phenoxyl radical. We also studied the formation of 2,4,5- complexes with β- and γ-cyclodextrins (2,4,5--β(γ)-CD) and the effect of this process on the rate of the steady-state photolysis of the herbicide.