Laboratory of Prostaglandin Chemistry

 

Head of the Laboratory: Yurij A. Piven'
Ph.D. (chemistry)

 

phone: +375 (17) 374-86-47
e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

 

About the Laboratory

Established in 1981.
From 1973 to 1981 the laboratory was headed by Fedor A. Lakhvich, academician of NASB, Laureate of State Prize of Republic of Belarus, professor, D.Sc.
Personnel: 9 researchers, including 1 academician and 5 Ph.D.

Research directions

  • Design and synthesis of natural and modified low-molecular weight bioregulators of prostaglandin and phytoprostane series, related bioactоve cyclopentanoids, butenolides, other heterocyclic compounds on the basis of ß-diketone and nitrile oxide methodologies
  • Development of environmentally friendly bio-rational plant protection products of new generation on the basis of natural insect- and phytohormones as well as their analogues mimicking the action of natural bioregulators or acting as their antagonists
  • Directed chemical structure modification of natural low-molecular weight bioregulators with the aim to develop modern effective pharmaceuticals and agrochemicals.

Main achievements and developments

  • Nitrile oxide methodology for the synthesis of prostanoids and related compounds. Directed synthesis of a number of prostanoids, steroids, pheromones (kairomones) of insects, polyketides and their biologically active analogues with the use of carbo- as well as heterocyclic ß-di- and ß-tricarbonyl compounds as universal synthons
  • Synthetic methods for ß-triketones and their selective reductive transformations. New chemical transformations of isoxazole derivatives which are the latent form of ß-diketones, ß-hydroxyketones, α,ß-unsaturated ketones etc.
  • Effective synthetic schemes for fluoro-substituted derivatives of natural flavonoids and triterpenoids of lupane series — promising anti-proliferative agents
  • Effective synthetic schemes for butenolide acetogenin ancepsenolide and related polyketides - analogues of lactone lignans, immunotropic hetero analogues of prostanoids of the series B and E on the basis of tetronic acids and their enol derivatives
  • Preparative synthetic methods for fluoro-substituted 2-acylcycloakane-1,3-diones and their derivatives — perspective precursors of new anticancer and anti-inflammatory drugs as well as pesticides of new generation
  • Effective chemical and bio-rational plant protection agents (herbicides Miodan, Shkwal, Taifun, Propolon; fungicides Laert, Echion; insecticides Vitan, Kerber, Biunic), pheromone compositions on the basis of 2-acylcyclohexane-1,3-diones for control of pests of grain stocks (Myrron and Parron) and of fruit crops (LP-U)
  • New technology for active pharmaceutical ingredient of anticancer drug "Carboplatin".

Selected publications

  1. Vostrikov N.S., Makaev Z.R., Zagitov V.V., Lakhvich F.A., Pashkovsky F.S., Miftakhov M.S. Methyl (S)-(5-methylidene-4-oxocyclopent-2-en-1-yl)acetate as a readily available pharmacologically important subunit of cross-conjugated cyclopentenone prostaglandins // Russian Chemical Bulletin. – 2020. – V. 69. – № 3. – P. 547-551.
  2. Khlebnicova T.S., Piven’ Yu.A., Lakhvich F.A., Sorokina I.V., Frolova T.S., Baev D.S., Tolstikova T.G. Betulinic Acid-Azaprostanoid Hybrids: Synthesis and Pharmacological Evaluation as Anti-inflammatory Agents // Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry. –  2020. – V. 19. – N. 3. – P. – P. 254–267.
  3. Khlebnikova T.S., Piven’ Yu.A., Isakova V.G., Smaliak V.A., Baranovsky A.V., Lakhvich F.A. One-Pot Synthesis of Trifluoromethyl-Substituted Imidazobenz[1,2-d]- and -[1,2-c]isoxazoles // Russian Journal of General Chemistry. – 2020. – V. 90. – № 4. – P. 746–749.
  4. Khlebnikova T.S., Piven’ Yu.A., Zinovich V.G., Baranovskii A.V., Rusanov É.B., Panibrat O.V., Ogurtsova S.É., Lakhvich F.A. Synthesis and Cytotoxic Activity of Fluorine-Containing 6,7-Dihydroindazolone and 6,7-Dihydrobenzisoxazolone Derivatives // Pharmaceutical Chemistry Journal. – 2020. – V. 54. – P. 700–706.
  5. Khlebnicova T.S., Piven’ Yu.A., Baranovsky A.V., Lakhvich F.A., Sorokina I.V.,  Tolstikova T.G. Fluorine-containing lupane triterpenoid acid derivatives: Design, synthesis and biological evaluation as potential anti-inflammatory agents // Steroids. – 2019. – V. 147. – P. 62-69.
  6. Khlebnicova T.S., Piven' Yu.A., Isakova V.G., Baranovsky A.V., Lakhvich F.A., Sorochinsky A.E., Gerus I.I. Regioselective Synthesis of Polyfluoroalkyl Substituted 6,7-Dihydrobenzisoxazolones // Journal of Heterocyclic Chemistry. – 2018. – V. 55. – N. 7. – P. 1791-1797.
  7. Gyrdymova Yu.V., Sudarikov D.V., Shevchenko O.G., Rubtsova S.A., Slepukhin P.A., Patov S.A., Lakhvich F.A., Pashkovskii F.S., Kuchin A.V. Synthesis and Antioxidant Activity of New Neomenthyl and Caranyl Thiotriazoles // Chemistry of Natural Compounds. – 2018. – V. 54. – P. 883–888.
  8. Khlebnicova T.S., Piven’ Yu.A., Lakhvich F.A., Frolova T.S., Sorokina I.V., Tolstikova  T.G.   Synthesis and Cytotoxicity of Conjugates of Betulinic Acid and F-Containing 2-Acylcycloalkane-1,3-Diones // Chemistry of Natural Compounds. – 2018. – V. 54. – P. 1100–1105.
  9. Pashkovskii F.S., Dontsu Yu.S., Rubinov D.B., Baranovskii A.V., Lakhvich F.A. Chemical Transformations of 5,5-Dimethyl-2-(3-aryl-4-nitrobutanoyl)cyclohexane-1,3-diones. Synthesis of 6,7-Dihydrobenzo[d]-isoxazol-4(5H)-ones and 6,7-Dihydro-1H-indazol-4(5H)-ones with Isoxazole and Isoxazoline Fragments in the Side Chain// Russian Journal of Organic Chemistry. – 2018. – V. 54. – N. 5. – P. 751–762.
  10. Pashkovskii F.S., Dontsu Yu.S., Rubinov D.B., Lakhvich F.A. Chemical Transformations of 2-(3-Aryl-4-nitrobutanoyl)-5,5-dimethylcyclohexane-1,3-diones: II. Synthesis of New 6,7-Dihydro-1,2-benzoxazol-4(5H)-ones with Functionalized Side Chain // Russian Journal of Organic Chemistry.  – 2018. – V. 54. – N. 6. – P. 844–854.
  11. Dontsu Yu.S., Pashkovskii F.S., Rubinov D.B., Lakhvich F.A. Synthesis of 2-[3-Aryl-3-(5-phenylisoxazol-3-yl)propyl] Derivatives of 5,5-Dimethylcyclohexane- and Cyclopenthane-1,3-diones Proceeding from 2-(4-Nitro-3-arylbutyl) Precursors // Russian Journal of Organic Chemistry. – 2018. – V. 54. – N. 8. – P. 1232–1240.
  12. Khlebnicova T.S., Piven’ Yu.A., Baranovsky A.V., Lakhvich F.A., Shishkina S.V., Zicāne D., Tetere Z., Rāviņa I., Kumpiņš V., Rijkure I., Mieriņa I., Peipiņš U., Turks M. Synthesis of novel lupane triterpenoid−indazolone hybrids with oxime ester linkage // Steroids. – 2017. – Vol. 117. – P. 77-89.
  13. Khlebnikova T.S., Piven’ Yu.A., Lakhvich F.A. Synthesis of New Betulonic Acid Conjugates with 2-Perfluoroacylcycloalkane-1,3-Diones Using Polymethylenediamine Linkers // Chemistry of Natural Compounds. – 2017. – V. 53. – P. 486–491.
  14. Khlebnikova T.S., Piveń Yu.A., Isakova V.G., Baranovsky A.V., Lakhvich F.A. Synthesis of fluorine-containing 6,7-dihydrobenzisoxazolones from 2-(fluorobenzoyl)cyclohexane-1,3-diones and their methyl enol ethers // Chemistry of Heterocyclic Compounds. – 2017. – V. 53. – № 11. – P. 1254–1260.
    Pashkovsky F.S., Dontsu J.S., Rubinov D.B., Lakhvich F.A. Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds.
  15. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones // Chemistry of Heterocyclic Compounds. – 2015. – Vol. 50. – N. 10. – P. 1421-1431.

 

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