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N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Of the Siberian Branch of Russian Academy of Science

 

Department of Medicinal Chemistry


salahutdinov

Laboratory of physiologically active substances (LPhAS)

(up to 2004 г - Laboratory Wood Chemistry and Biologically Active Compounds - LFC&BAC)


Head - Doctor of Chemical Sciences, Professor- Nariman F. Salakhutdinov

phone +7 (383) 330-97-33, Fax: +7 (383) 330-97-52, internal phone: 3-75, email:This email address is being protected from spambots. You need JavaScript enabled to view it.

 

 

Short history

 

Laboratory of physiologically active substances (up to 2012 – Laboratory of forest chemistry and natural biologically active compounds) was established as a division of the Department of Medical Chemistry, Novosibirsk Institute of Organic Chemistry SB RAS. Its personnel is based on the staff of the laboratory of cationic reactions NIOCh SB RAS (before 2004 – head Prof. V. A. Barkhash). At present, it is a unit equipped with modern scientific instruments and personnel of  high qualification. The staff of the lab has 20 employees, including two full professors and 14 PhD’s.


Staff

Employee Position Room Phone Phone in. email Publications
by yearsby tipeby If
1 Salakhutdinov Nariman Faridovich Head of Depart. (Doct. Chem.) 310 НТК 330-97-33 3-75 This email address is being protected from spambots. You need JavaScript enabled to view it.
2 Volcho Konstantin Petrovich Chief Researcher (Doct. Chem.) 129, 311 НТК 330-88-70 3-96, 3-01 This email address is being protected from spambots. You need JavaScript enabled to view it.
3 Chief Researcher (Doct. Chem.)
4 Luzina Olga Anatolievna Leading Researcher (Doct. Chem) 204 330-88-70 2-57, 2-21 This email address is being protected from spambots. You need JavaScript enabled to view it.
5 Yarovaya Olga Ivanovna Leading Researcher (Doct. Chem) 205 330-88-70 2-25 This email address is being protected from spambots. You need JavaScript enabled to view it.
6 Ardashov Oleg Vasilievich Senior Researcher (Cand. Chem.) 129 330-88-70 3-96 This email address is being protected from spambots. You need JavaScript enabled to view it.
7 Il'ina Irina Viktorovna Senior Researcher (Cand. Chem.) 129 330-88-70 3-96 This email address is being protected from spambots. You need JavaScript enabled to view it.
8 Rogachev Artem Dmitrievich Senior Researcher (Cand. Chem.) 330 330-97-47 2-36 This email address is being protected from spambots. You need JavaScript enabled to view it.
9 Salomatina Oksana Vladimirovna Senior Researcher (Cand. Chem.) П-042 330-88-70 2-55 This email address is being protected from spambots. You need JavaScript enabled to view it.
10 Khomenko Tatyana Mikhailovna Senior Researcher (Cand. Chem.) 103 330-88-70 4-46 This email address is being protected from spambots. You need JavaScript enabled to view it.
11 Researcher (Cand. Chem.)
12 Researcher (Cand. Chem.)
13 Zakharova Olga Dmitrievna Researcher (Cand. Chem.)
14 Laev Sergey Sergeevich Researcher (Cand. Chem.) 409 НТК 2-38 This email address is being protected from spambots. You need JavaScript enabled to view it.
15 Nechepurenko Ivan Vasilievich Researcher (Cand. Chem.) 330 330-88-70; 8-983-124-30-49 2-36 This email address is being protected from spambots. You need JavaScript enabled to view it., This email address is being protected from spambots. You need JavaScript enabled to view it.
16 Patrusheva Oxana Stanislavovna Researcher (Cand. Chem.) 129 330-88-70 3-96 This email address is being protected from spambots. You need JavaScript enabled to view it.
17 Popadyuk Irina Igorevna Researcher (Cand. Chem.) П-042 330-88-70 2-55 This email address is being protected from spambots. You need JavaScript enabled to view it.
18 Sokolova Anastasiya Sergeevna Researcher (Cand. Chem.) 205 330-88-70 2-25 This email address is being protected from spambots. You need JavaScript enabled to view it.
19 Fomenko Vladislav Viktorovich Researcher (Cand. Chem.) 302 330-97-47 2-02 This email address is being protected from spambots. You need JavaScript enabled to view it.
20 Komarova Nina Ivanovna Leading Engineer 308 330-97-47 2-84 This email address is being protected from spambots. You need JavaScript enabled to view it.
21 Kurbakova Svetlana Yurievna Leading Engineer 129 330-88-70 3-96 This email address is being protected from spambots. You need JavaScript enabled to view it.
22 Mainagashev Ilia Yakovlevich Leading Engineer 330 330-88-70 2-36 This email address is being protected from spambots. You need JavaScript enabled to view it.
23 Blokhin Mikhail Evgenievich engineer 204 330-88-70 2-21 This email address is being protected from spambots. You need JavaScript enabled to view it.
Students
24 Baranova Darya Vitalievna laboratory assistant 205 330-88-70 2-25 This email address is being protected from spambots. You need JavaScript enabled to view it.
25 Okhina Alina Aleksandrovna laboratory assistant 330 330-88-70 2-36
26 Putilova Valentina Pavlovna laboratory assistant 205 330-88-70 2-25 This email address is being protected from spambots. You need JavaScript enabled to view it.
27 Mordvinova Ekaterina Borisovna laboratory assistant
PHD Students
28 Ivankin Dmitry Igorevich engineer 302, 330 330-97-47 2-02, 2-36 This email address is being protected from spambots. You need JavaScript enabled to view it.

The major scientific trends

 

  • Development of new leading compounds in the most popular therapeutic areas – oncology, cardiovascular diseases, neurodegenerative diseases, analgesics, and infectious disease.
  • Reactivity study of monoterpenoids in the presence of heterogeneous catalysts. Development of effective methods of catalytic conversions of organic compounds in supercritical fluids.
  • Development of methods for the stereoselective synthesis, including new catalytically asymmetric systems.
  • Directed chemical modification of metabolites of plant and animal origin in order to obtain new semisynthetic derivatives of valuable biological properties.
  • The study of Siberian and Altai plants as a scientific basis for the development of Russian medical and preventive medications.

 

Main scientific results

 

  • A new promising agent for the treatment of Parkinson's disease, who is at the stage of pre-clinical trials, was developed. Based on polysulfur compounds, an agent having high antidepressant activity, superior to that of some commercial products, was created. Compounds perspective for the development of a new structural type of analgesics, anticonvulsants were found.
  • As a result of the reactivity study of the usnic acid which is a metabolite of a number of lichens, new highly active anti-TB and anti-influenza agents have been developed.
  • New catalytic systems for the asymmetric oxidation of sulfides to sulfoxides and asymmetric chiral addition of diethylzink to aldehydes were created. Patent collision-free methods of asymmetric synthesis of the modern anti-ulcer drug "Esomeprazole" with the use of original catalytic systems were developed.
  • As a result of phytochemical studies it was found that the roots of barberry Berberis sibirica Pall, both natural and introduced populations growing in Russia, are a practical source of isoquinoline alkaloid berberine. A technique which allows the isolation of berberine chloride with the yield up to 0.62% on the dry weight of roots was developed and patented. A review summarizing the reactions of berberine and its hydrogenated derivatives, as well as information on the biological activity of berberine and some of its derivatives was published. Methods of the direct introduction of bromine and iodine in the molecule of berberine were developed in first time.
  • New semisynthetic derivative of glycyrrhetic acid, methyl soloksolon, having anticancer and anti-inflammatory activities was obtained. Its preclinical in vitro and in vivo tests have shown a high potential of this compound as a high-performance low-toxic agent in the drug development.
  • Chemical transformations of stilbene glycosides, resveratroloside and pinostilbenoside  were performed and their derivatives were obtained. It was found that resveratroloside had cardioprotective properties comparable to those of resveratrol.

 

List of priority investigations

 

  • Scientific basis of isolation technologies of plant metabolites of Siberian flora as a raw material source promising synthons for medicinal chemistry and pharmaceutical industries.
  • Synthetic transformation of plant alkaloids, terpenoids and coumarins. The total synthesis of the substances of high pharmacological importance

 

Current projects

  • RFBR Projects:
    • Creation of a basic foundation for the development of technological methods for the synthesis of physiologically active compounds from the available monoterpenoids using supercritical solvents (11-08-00171-a);
    • Creation of anti-cancer polysulfide compounds PPAR1 inhibitors (11-04-12099-ofi-m-2011);
    • The study of the fundamental laws of interaction of monoterpenoids with aromatic aldehydes to detect antiparkinsonian agents of a new structural type (11-03-00010-a);
    • Identification of the fundamental laws of the reactivity of pinane terpenoids in the presence of acidic crystalline aluminosilicate catalysts to discover new pharmacologically active compounds (10-03-00230-a);
    • The development of selective functionalization methods of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol at the methyl groups to study the effects of substituents on the antiparkinsonian activity (12-03-31257 mol_a);
    • The reactivity study of carbonyl compounds of monoterpene type in the reactions with different nitrogen-containing derivatives of adamantane to find new anxiolytic agents (12-03-31392 mol_a). Integration projects:
    • A study of genetic and neurophysiological mechanisms of actions of the brain-derived neurotrophic factor and its synthetic agonists);
    • A study of metabolites of marine and plant origin as a scientific basis for the development of important drugs;
    • Integration project of SB RAS on partner basic research No 30 (2012-2013 years) "Development of long-acting form of the neurotoxin to relieve arrhythmia on in vivo model of atrial fibrillation";
    • Search and creation of products for cancer therapy based on modified natural compounds.
  • RAS and SB RAS presidium programmes:
    • The origin of life and the formation of the biosphere (Natural clays as catalysts for prebiotic reactions of chiral compounds);
    • Development of effective anticancer agents based on modified natural triterpene acids (the program "Basic Sciences for Medicine" of SB RAS);
    • Expedition project "Survey of plants of Siberia and Altai as a scientific basis for the development of domestic medicinal and preventive drugs." State contract.
    • "Preclinical studies of TB drugs based on semi-synthetic derivatives of usnic acid" (within the Federal Target Program "Development of the medical and pharmaceutical industry of the Russian Federation for the period up to 2020 and beyond"). 12411.1008799.13.002 (2012).

 

Selected publications

 

  1. Tatyana G. Tolstikova, Alla V. Pavlova, Ekaterina A. Morozova, Tatyana M. Khomenko, Konstantin P. Volcho, Nariman F. Salakhutdinov. The Analgesic Activity of 8-(Trifluoromethyl)-1,2,3,4,5-benzopentathiepine-6-amine and Its Hydrochloride. Letters in Drug Design & Discovery, 2012, 9, 513-516.
  2. Zakharenko A., Sokolov D., Luzina O., Sukhanova M., Khodyreva S., Zakharova O., Salakhutdinov N., Lavrik O. Influence of Usnic Acid and its Derivatives on the Activity of Mammalian Poly(ADP-ribose)polymerase 1 and DNA Polymerase. Medicinal Chemistry, 2012, 8, 883-893.
  3. I. V. Il`ina, V. P. Sivcev, K. P. Volcho, N. F. Salakhutdinov, V. I. Anikeev. The Meerwein-Ponndorf-Verley type reaction in a mixture of supercritical isopropanol/CO2 in a continuous flow reactor in the presence of alumina. J. Supercritical Fluids, 2012, 61, 115–118.
  4. Dmitriy N. Sokolov, Vladimir V. Zarubaev, Anna A. Shtro, Marina P. Polovinka, Olga A. Luzina, Nina I. Komarova, Nariman F. Salakhutdinov, Oleg I. Kiselev. Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009. Bioorg. Med. Chem. Letters, 2012, 22, 7060–7064
  5. V. P. Sivcev, K. P. Volcho, N. F. Salakhutdinov, V. I. Anikeev. Transformations of acetophenone and its derivatives in supercritical fluid isopropanol/CO2 in a continuous flow reactor in the presence of alumina. J. of Supercritical Fluids, 2012, 70, 35–39.
  6. Alexander V. Kulikov, Maria A. Tikhonova, Elizabeth A. Kulikova, Konstantin P. Volcho, Tatyana M. Khomenko, Nariman F. Salakhutdinov, Nina K. Popova. A new synthetic varacin analogue, 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride (TC-2153), decreased hereditary catalepsy and increased the BDNF gene expression in the hippocampus in mice. Psychopharmacology, 2012, 221, 469–478.
  7. Рогачев А. Д., Комарова Н. И., Поздеева А. В., Корчагина Д. В., Васильев В. Г., Салахутдинов Н. Ф., Толстиков Г. А. Взаимодействие некоторых производных гликозидов резвератрола с гипохлоритами в различных средах. Химия Природ. Соедин., 2012, №1, 5-11.
  8. Zakharenko A. L., Salomatina O. V., Sukhanova M. V., Kutuzov M. M., Ilina E. S., Khodyreva S. N., Schreiber V., Salakhutdinov N. F., Lavrik O. I. Glycyrrhetinic acid and its derivatives as inhibitors of poly(ADP-ribose)polymerases 1 and 2, apurinic/apyrimidinic endonuclease 1 and DNA polymerase. Biopolymers and Cell, 2012, 28, 223–228.
  9. И. В. Нечепуренко, Н. И. Комарова, В. Г. Васильев, Н. Ф. Салахутдинов. Синтез аналогов берберинбромида, содержащих фрагмент третичных амидов уксусной кислоты в 9-О-положениии. Химия Природ. Соедин., 2012, №6, 924-929.
  10. Ardashov O. V., Pavlova A. V., Il’ina I. V., Morozova E. A., Korchagina D. V., Karpova E. V., Volcho K. P., Tolstikova T. G., Salakhutdinov N. F. Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease. J. Med. Chem., 2011, 54, 3866-3874.
  11. И. В. Нечепуренко, У. А. Боярских, Н. И. Комарова, М. П. Половинка, М. Л. Филипенко, Г. И. Лифшиц, Н. Ф. Салахутдинов, Г. А. Толстиков. Влияние берберина и его бром- и иодпроизводных на уровень экспрессии гена рецептора ЛПНП в клетках HepG2. Доклады АН, 2011, 439, 346–350.
  12. Ekaterina A. Koneva, Evgeniy V. Suslov, Dina V. Korchagina, Alexander M. Genaev, Konstantin P. Volcho, Nariman F. Salakhutdinov. Catalytic asymmetric addition of diethylzinc to benzaldehyde using ?-pinene-derived ligands. The Open Catalysis Journal, 2011, 4, 107-112.
  13. Irina V. Il’ina, Konstantin P. Volcho, Oksana S. Mikhalchenko, Dina V. Korchagina and Nariman F. Salakhutdinov. Reactions of Verbenol Epoxide with Aromatic Aldehydes Containing Hydroxy or Methoxy Groups in the Presence of Montmorillonite Clay. Helvetica Chimica Acta, 2011, 94, 502-513.
  14. Ardashov O. V., Zarubaev V. V., Shtro A. A., Korchagina D. V., Volcho K. P., Salakhutdinov N. F., Kiselev O. I. Antiviral activity of 3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol and its derivatives against influenza A(H1N1)2009 virus. Letters in Drug Design & Discovery, 2011, 8, 375-380.
  15. Logashenko E.B., Salomatina O.V., Markov A.V., Korchagina D.V., Salakhutdinov N.F., Tolstikov G.A., Vlassov V.V., Zenkova M.A. Synthesis and Pro-Apoptotic Activity of Novel Glycyrrhetinic Acid Derivatives. ChemBioChem, 2011, 12, 784-794.
  16. D. N. Sokolov, O. A. Luzina, D. V. Korchagina, M. P. Polovinka, N. F. Salakhutdinov. Reaction of (+)-usninic acid and several of its derivatives with diazomethane. Chemistry of Natural Compounds, 2011, 47, 708-712.
  17. И. В. Нечепуренко, М. П. Половинка, Н. И Комарова, Н. Ф. Салахутдинов, Г. А. Толстиков. Способ получения пакистанамина и берберина хлорида из Berberis sibirica. Патент РФ, 2010, RU2423992 C1.
  18. Salomatina O.V., Logashenko E.B., Korchagina D.V., Salakhutdinov N.F., Tolstikov G.A., Vlassov V.V., Zenkova M.A. Synthesis and Biological Activity of Novel Glycyrrhetic Acid Derivatives. Doklady Chemistry, 2010, 430, 35–38.
  19. Саломатина О. В., Салахутдинов Н. Ф., Толстиков Г. А., Логашенко Е. Б., Зенкова М. А., Власов В. В. Противоопухолевое средство тритерпеновой природы, полученное путем модификации глицирретовой кислоты. Патент РФ № 2401273, 2010.
  20. И. В. Нечепуренко, Н. Ф. Салахутдинов, Г. А. Толстиков. Берберин: химия и биологическая активность. Химия в интересах устойчивого развития, 2010, 18, 1-23.
  21. Толстикова Т. Г., Павлова А. В., Морозова Е. А., Ардашов О. В., Ильина И. В., Волчо К. П., Салахутдинов Н. Ф., Толстиков Г. А. Высокоэффективное противопаркинсоническое средство нового структурного типа. Доклады АН. Физиология, 2010, 435, 708–710.
  22. Толстикова Т. Г., Павлова А. В., Долгих М. П., Ильина И. В., Ардашов О. В., Волчо К. П., Салахутдинов Н. Ф., Толстиков Г. А. Новый высокоэффективный противосудорожный агент – (4S,5R,6R)-пара-мента-1,8-диен-5,6-диол. Доклады АН. Физиология, 2009, 429, 139–141.
  23. Suslov E. V., Volcho K. P., Salakhutdinov N. F. Basic zeolites and mesoporous materials in Knoevenagel and Michael reactions. Handbook of Zeolites: Structure, Properties and Applications. Ed. T. W. Wong. Hauppauge: Nova Science Publishers, 2009. ISBN 9781607410461, 676 p.
  24. И. В. Нечепуренко, Н. И. Комарова, Ю. В. Герасимова, В. В. Коваль, М. П. Половинка, Д. В. Корчагина, Н. Ф. Салахутдинов. Изучение структуры олигомерных проантоцианидинов корней Hedysarum theinum методами тиолиза и МС MALDI-TOF. Химия Природ. Соедин., 2009, №1, 30-36.
  25. Суслов Е. В., Волчо К. П., Покровский А. Г., Салахутдинов Н. Ф. Ингибитор репродукции вируса иммунодефицита. Патент РФ №2007139397б 2009.
  26. Ilina I. V., Suslov E. V., Khomenko T. M., Korchagina D. V., Volcho K. P., Salakhutdinov N. F. Natural montmorillonite clay as prebiotic catalyst. Paleontological Journal, 2009, 43, 958–964.
  27. T. M. Khomenko, T. G. Tolstikova, A. V. Bolkunov, M. P. Dolgikh, A. V. Pavlova, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov. 8-(Trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine: Novel Aminobenzopentathiepine having In Vivo Anticonvulsant and Anxiolytic Activities. Letters in Drug Design & Discovery, 2009, 6, 464-467.
  28. Ekaterina A. Koneva, Konstantin P. Volcho, Yuri V. Gatilov, Dina V. Korchagina, Georgi E. Salnikov, Nariman F. Salakhutdinov. Synthesis of the Derivatives of the Optically Active b-Amino Acids from (+)-2-Carene. Helvetica Chimica Acta, 2008, 91, 1849-1856.
  29. K. P. Volcho, N. F. Salakhutdinov. Transformations of Terpenoids on Acidic Clays. Mini Reviews in Organic Chemistry, 2008, 5, 345-354.
  30. Хоменко Т. М., Волчо К. П., Комарова Н. И., Салахутдинов Н. Ф. Эффективный способ получения эзомепразола с использованием комплекса хиральных лигандов. ЖОрХ, 2008, 44, 126–129.
  31. Ильина И. В., Волчо К. П., Салахутдинов Н. Ф. Кислотно-катализируемые превращения терпеноидов пинанового ряда – новые возможности. ЖОрХ, 2008, 44, 11–31.
  32. Конева Е. А., Хоменко Т. М., Курбакова С. Ю., Комарова Н. И., Корчагина Д. В., Волчо К. П., Салахутдинов Н. Ф., Толстиков А. Г., Толстиков Г. А. Получение оптически активного омепразола с использованием каталитических комплексов ионов ванадия с хиральными основаниями Шиффа. Изв. РАН. Сер. Хим., 2008, №8, 1648-1653.
  33. Irina V. Il’ina, Konstantin P. Volcho, Dina V. Korchagina, Vladimir A. Barkhash, Nariman F. Salakhutdinov. Reactions of Allyl Alcohols of the Pinane Series and of Their Epoxides in the Presence of Montmorillonite Clay. Helvetica Chimica Acta, 2007, 90, 353-368.
  34. Salomatina O. V., Kuznetsova Т. G., Korchagina D. V., Paukshtis E. A., Moroz E. M., Volcho K. P., Barkhash V. A., Salakhutdinov N. F. Effects of the properties of ZrO2/SO4 solid-phase catalysts on the products of (+)-limonene diepoxides transformation and reaction mechanism. J. Mol. Cat. A: Chemical, 2007, 269, 72-80.
  35. Саломатина О. В., Салахутдинов Н. Ф., Толстиков Г. А., Логашенко Е. Б., Зенкова М. А., Власов В. В. Противоопухолевое средство тритерпеновой природы. Патент РФ № 2393165, 2008.