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2010 year, number 4

1.
Antituberculosis Activity of Natural and Synthetic Compounds

L. N. Rogoza, N. F. Salakhutdinov, G. A. Tolstikov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
rogoza@nioch.nsc.ru
Keywords: tuberculosis, tuberculosis with plural drug resistance, M. tuberculosis, antimycobacterial activity, antituberculosis activity, cytotoxicity, structure-property relationship
Pages: 343-375

Abstract >>
The review presents the most active natural and synthetic compounds those exhibit antimycobacterial activity providing the minimum inhibiting concentration (MIC) ≤ 5 μg/mL. For better understanding the structure-activity relationship, compounds with a high value of MIC are considered in some cases. The review covers the papers published within the range of 2001-first half of 2009. The information in the review is systematized with respect to chemical structures (the nitrogen-, oxygen-, sulphur-containing heterocyclic compounds, peptides, alkaloids, terpenoids and others.).



2.
Effect of the Nature of Exchange Cations in Montmorillonite Clay on the Direction of Verbenol Epoxide Transformations

I. V. Il'ina, S. Y. Kurbakova, K. P. Volcho, N. F. Salakhutdinov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
volcho@nioch.nsc.ru
Keywords: montmorillonite clay, verbenol epoxide, terpenoids, rearrangements
Pages: 377-380

Abstract >>
Transformations of (-)-cis-verbenol epoxide 1 in the presence of montmorillonite clay containing different exchange cations were studied for the first time. It was demonstrated that the nature of a cation exerts a substantial effect both on the contribution from undesirable resinification and on the distribution of low-molecular products. The use of Co2+-containing montmorillonite clay allowed us to obtain a substantial (1.5 times) increase in the content of the target compound 3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 2 in reaction mixture comparing to acidic montmorillonite clay species used earlier.



3.
Synthesis and Investigation of the Pharmacological Activity of Oreoselone Nitrogen-Containing Derivatives

A. V. Lipeeva, E. E. Shults, E. A. Morozova, T. G. Tolstikova, G. A. Tolstikov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
morozova@nioch.nsc.ru
Keywords: furocoumarins, bromoreoselone, 2-(1, 3-dibromopropane-2-ylidene)-2Н-furo-[3, 2-g][1]benzopyran-3, 7-dione, motion activity, chloral hydrate sleep
Pages: 381-388

Abstract >>
The bromination of peucedanine using different reagents resulted in the formation of 2-bromoreoselone. Via the reaction with the derivatives of piperidine and piperazine we synthesized 2-piperazino and 2-piperidino derivatives of oreoselone. Conditions were determined for the formation of 2-(1,3-dibromopropane-2-ylidene)-2Н-furo-[3,2-g][1]-benzopyran-3,7-dione. The interaction of the latter with tyramine resulted in obtaining bis(diaminophenethyl) derivative of furocoumarin. The amination of the mentioned dibromide with the help of spermine resulted in the formation of a macrocyclic compound containing both furocoumarin and polyamine fragments. The effect of novel oreoselone derivatives on the central nervous system was investigated.



4.
Computer Analysis of Biological Activity Spectrum for Novel Betulonic Acid Derivatives

D. S. Baev, I. V. Sorokina, T. G. Tolstikova
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
sorokina@nioch.nsc.ru
Keywords: derivatives of betulonic acid, structure-to-properties relations, PASS program
Pages: 389-395

Abstract >>
Analysis of the structure-to-properties relations for the new derivatives of betulonic acid was carried out with the help of PASS program. Agents with potentially high antitumor, hepatoprotective and anti-inflammatory activity were revealed among these compounds. Analysis of the possible mechanisms of the action of novel betulonic acid derivatives was carried out.



5.
Synthesis and Biological Activity of Novel Acetylene Betulonic Acid Derivatives

A. I. Govdi1, I. V. Sorokina2, T. G. Tolstikova2, S. F. Vasilevsky1, G. A. Tolstikov2
1 Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences
2 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
sorokina@nioch.nsc.ru, vasilev@kinetics.nsc.ru
Keywords: triterpenoids, betulonic acid, aryl acetylenes, hepatoprotective activity, anti-inflammatory activity
Pages: 397-402

Abstract >>
Acetylene derivatives of betulonic acid amide were synthesized. Their hepatoprotective and anti-inflammatory activity was investigated. In the series of betulonic acid derivatives, two compounds with a substantial hepatoprotective and anti-inflammatory effect were revealed.



6.
Effect of Betulonic Acid and Its Derivatives on the Morphology of Kidneys in the Animals with Transplanted Lewis Lung Carcinoma at the Background of Polychemotherapy and without It

N. A. Zhukova1, I. V. Sorokina1, T. G. Tolstikova1, M. P. Dolgikh1, D. E. Semenov2
1 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
2 Scientific Research Institute of Regional Pathology and Pathomorphology, Siberian Branch of the Russian Academy of Medical Sciences
sorokina@nioch.nsc.ru
Keywords: polychemotherapy, Lewis lung carcinoma, nephroprotective effect, betulonic acid, [3-oxo-20(29)-lupen-28-oyl]-3-aminopropionic acid and their methyl esters
Pages: 403-408

Abstract >>
Effect of betulonic and [3-oxo-20(29)-lupen-28-oyl]-3-aminopropionic acids and their methyl esters on the morphology of kidneys of the C57BL/6 mice with transplanted Lewis pulmonary adenocarcinoma at the background of cytostatic polychemotherapy (cyclophosphane, adriamycin, vincrystine, prednisolone) and without it was investigated. It was established by means of morphometry that the introduction of betulonic and [3-oxo-20(29)-lupen-28-oyl]-3-aminopropionic acids and their methyl esters against the background of polychemotherapy and without it has a positive effect on the course of tubulointerstitial nephropathy as it reduces the degree of necrotic and dystrophic changes of epithelial cells of proximal tubules as well as reduces the edema of interstitial tissue.



7.
Analgesic Activity of Some Furanoditerpenoids of Labdanum Series and Their Derivatives

E. A. Morozova, T. G. Tolstikova, E. E. Shults, S. V. Chernov, Y. V. Kharitonov, M. E. Mironov, G. A. Tolstikov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
morozova@nioch.nsc.ru
Keywords: lambertianic acid, flomizoic acid, analgesic activity
Pages: 409-414

Abstract >>
Derivatives of labdanum triterpenoids - lambertianic and flomizoic acids and their esters, modified in the heterocyclic fragment of the molecule, were obtained. Their analgesic activity was investigated.



8.
Hydroxyketones of para-Menthane Series as Promising Analgesic

A. V. Pavlova, T. G. Tolstikova, E. A. Morozova, O. V. Ardashov, I. V. Il'ina, K. P. Volcho, N. F. Salakhutdinov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
volcho@nioch.nsc.ru
Keywords: monoterpenoids of para-menthane series, analgesic activity, mice
Pages: 415-417

Abstract >>
Data obtained in the investigation of the analgesic activity of monoterpenoid of the para-menthane series - 2-hydroxy-3-methyl-6-(1-methylethenyl)cyclohex-3-enone are presented. It is discovered that two its spatial isomers (2R,6S and 2S,6R) in the dose of 2.5 mg/kg exhibit high analgesic activity and to a substantial extent quench the development of pain syndrome caused by the introduction of acetic acid. With the hot plate model, a substantial effect of the absolute configuration of the terpenoid on the direction of action is demonstrated.



9.
Derivatives of Methyllambertianate as Promising Correctors of Cytostatics with Hepatoprotective and Hemostimulating Activity

I. V. Sorokina, T. G. Tolstikova, D. S. Baev, N. A. Zhukova, Y. V. Kharitonov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
sorokina@nioch.nsc.ru
Keywords: methyllambertianate, hepatoprotective, antioxidant, hemostimulating activity
Pages: 419-424

Abstract >>
Results of the development of three original labdanum antioxidants based on the methyl ester of lambertianic acid, an available plant metabolite of Siberian pine Pinus sibirica R. Mayr. are presented. As a result of screening with the model of toxic CCl4-hepatitis induced in mice, the agents surpassing the known flavonoid dihydroquercetin in the anticytolytic and anticholestase action. It is shown that under the conditions of hemodepression caused by the introduction of cytostatic preparation cyclophosphane to rats, the compounds significantly decrease leukopenia by increasing the number of granulocytes and monocytes in blood. At the background of cyclophosphane, the derivatives of methyllambertianate exhibit higher antioxidant activity than dihydroquercetin does. The azlactone demonstrates pronounced anticholestase properties. The pharmacological properties discovered in the new derivatives of lambertianic acid allow considering them as potential correctors of chemotherapeutical preparations.



10.
Ethynylation of Lappaconitine as a Route to Modification of Alkaloids

A. A. Stepanov1, S. F. Vasilevsky1, G. A. Tolstikov2
1 Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences
2 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
vasilev@kinetics.nsc.ru
Keywords: Sonogashira reaction, new groups of acetylenic derivatives of lappaconitine, terminal 1, 3-butadiyne
Pages: 425-430

Abstract >>
Methods of the synthesis of a new group of acetylenic derivatives of lappaconitine were developed using Sonogashira reaction, starting from 5′-iodolappaconitine and terminal acetylenes in the system Pd(PPh3)2Cl2-CuI-Et3N. Terminal 1,3-butadiyne was introduced into lappaconitine molecule for the first time.



11.
Synthesis and Biological Activity of the Derivatives of 2,4,6,8,10,12-Hexaazatetracyclo[5.5.0.03,11.05,9]dodecane

T. G. Tolstikova1, E. A. Morozova1, S. V. Sysolyatin2, A. I. Kalashnikov2, Y. I. Zhukova2, V. N. Surmachev2
1 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
2 Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
Tolstikova tg_tolstikova@mail.ru, admin@ipcet.ru
Keywords: derivatives of 2, 4, 6, 8, 10, 12-hexaazatetracyclo[5.5.003, 11.05, 9]dodecane, anticonvulsive, anti-anxiety activity, mice
Pages: 431-436

Abstract >>
Synthesis of the derivatives of 2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane is described; their biological activity is investigated.



12.
Complexing of Pharmacons with Glycyrrhizic Acid as a Route to the Development of the Preparations with Enhanced Efficiency

A. V. Dushkin1, E. S. Meteleva1, T. G. Tolstikova2, M. V. Khvostov2, M. P. Dolgikh2, G. A. Tolstikov2
1 Institute of Solid State Chemistry and Mechanochemistry, Siberian Branch of the Russian Academy of Sciences
2 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
dushkin@solid.nsc.ru
Keywords: complexing, glycyrrhizic acid, pharmaceutical dosage forms, enhancement of drug efficiency
Pages: 437-444

Abstract >>
Gel chromatographic investigation of the aqueous solutions of glycyrrhizic acid was carried out. A mechanochemical route to obtaining its compositions with poorly soluble pharmaceutical substances was developed, the characteristics of their aqueous solutions were studied, and their pharmacological characteristics were examined.



13.
Investigation of Biological Safety of Nanosubstances and Nanomaterials

T. G. Tolstikova1, E. A. Morozova1, M. V. Khvostov1, P. P. Laktionov2, E. S. Morozkin2, Z. R. Ismagilov3, O. Y. Podyacheva3, S. V. Sysolyatin4, A. B. Vorozhtsov4, R. K. Tukhtaev5, C. N. Barnakov6
1 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
2 Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences
3 Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences
4 Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
5 Institute of Solid State Chemistry and Mechanochemistry, Siberian Branch of the Russian Academy of Sciences
6 Institute of Coal and Coal Chemistry, Siberian Branch of the Russian Academy of Sciences
Keywords: metal nanopowder, toxicity, in vivo, in vitro
Pages: 445-452

Abstract >>
Results of the toxicological investigation in vivo and in vitro of nanosubstances and nanomaterials obtained at the Institutes of the Siberian Branch of the RAS are presented. It was established that, on the basis of acute toxicity value, the nanopowders of the oxides of aluminium, zinc, titanium, and carbon materials may be related to the class 3 (moderately toxic) or the class 4 (low toxicity), while nanopowders of copper correspond to the class 2 of toxicity. It is demonstrated through the in vitro investigation involving titanium nanopowder as an example that metal nanopowders can be highly toxic for various primary (healthy) cells but cause no death of cancer cells.



14.
Pharmacological Properties of the Complexes of Plant Carbohydrate-Containing Metabolites with the Agents Affecting the Cardiovascular System

M. V. Khvostov, A. O. Bryzgalov, T. G. Tolstikova
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
mihail.hvostov@gmail.com
Keywords: complexes, plant metabolites, antihypertensive and antiarrythmic properties
Pages: 453-459

Abstract >>
Antihypertensive and antiarrythmic properties of the complexes of glycyrrhizic acid (glycoside of licorice roots), glycosides of Stevia rebaudiana Bertoni (stevioside, enzymatically treated stevioside SWETA and rebaudioside), arabinogalactan (polysaccharide of Siberian Larch) with propranolol, amiodarone and nifedipine were investigated. It was established that all the studied complexes of nifedipine except the complex of nifedipine with rebaudioside at the molecular ratio of 1 : 4 are promising for further pharmacological examination. The complex of propranolol with glycyrrhizic acid at the molecular ratio of 1 : 4 in the dose of 0.0025 mg/kg is also distinguished; it demonstrated good antiarrythmic activity. In the case of complexes with amiodarone, it may be concluded that complexing of this pharmacon with carbohydrate-containing plant metabolites used in our experiments does not lead to the desirable decrease in efficient dose but, quite contrary, worsens its antiarrythmic effect.