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Traven V.F.,Mendeleev University of Chemical Technology | Ivanov I.V.,Mendeleev University of Chemical Technology | Lebedev V.S.,Mendeleev University of Chemical Technology | Chibisova T.A.,Mendeleev University of Chemical Technology | And 6 more authors.
Russian Chemical Bulletin | Year: 2010

According to 1H and 13C NMR data, enamines of 3-formyl-4-hydroxycoumarin exist in the keto enamine tautomeric form and undergo Z/E-isomerization around the C=C bond in CDCl3, DMSO-d6, and CD3OD at room temperature. The activation energies of E/Z-isomerization were measured experimentally and calculated by the B3LYP/6-311++G(d,p) method. An X-ray diffraction study showed that 3-(benzyliminomethyl)chromane-2,4-dione in the crystalline state exists as a mixture of two keto enamine isomers. © 2010 Springer Science+Business Media, Inc.


Traven V.F.,Mendeleev University of Chemical Technology | Ivanov I.V.,Mendeleev University of Chemical Technology | Lebedev V.S.,Mendeleev University of Chemical Technology | Solov'Eva N.P.,Center for Drug Chemistry | And 4 more authors.
Heterocyclic Communications | Year: 2010

Imines of 7-dialkylamino-3-formyl-4-hydroxycoumarins have been found to exist in Z -ketoenamine form in crystal state and undergo Z/E -isomerization around C = C bond in organic solvents at room temperature. Activation energies of isomerization have been measured experimentally and calculated by the DFT B3LYP method. Transition of ketoenamine form of p -nitrophenylimines into (hydroxy)imine form at low concentration (10-5 m ) in polar solvents is accompanied by strong increase in fluorescence.


Komarova E.S.,Russian Academy of Sciences | Makarov V.A.,Russian Academy of Sciences | Granik V.G.,Center for Drug Chemistry | Parkanyi C.,Florida Atlantic University
Journal of Heterocyclic Chemistry | Year: 2012

The procedures for the synthesis of substituted pyrazolo[3,4-b]pyridine-6- ones and some of their properties are reviewed. © 2012 HeteroCorporation.


Medvedeva M.I.,Mendeleev University of Chemical Technology | Tugusheva N.Z.,Center for Drug Chemistry | Alekseeva L.M.,Center for Drug Chemistry | Chernyshev V.V.,Moscow State University | And 2 more authors.
Russian Chemical Bulletin | Year: 2010

Methyl 3-amino-4-arylaminothieno[2,3-b]pyridine-2-carboxylates containing various substituents in the benzene ring were synthesized by the Thorpe-Ziegler reaction of 4-arylamino-2-chloropyridine-3-carbonitriles with methyl thioglycolates. The influence of the substituent in the benzene ring, acetal structure, the solvent and the process temperature on the reactions of obtained compounds with amide acetals was studied. It was established that reactions with dimethylacetamide dimethylacetal in toluene smoothly results in amidine derivatives, viz., methyl 4-arylamino-3-[1-(dimethylamino)ethylidene] aminothieno[2,3-b]pyridine-2-carboxylates, regardless of the substituent in the benzene ring. Analogous reaction of p-fluoroderivative with dimethylacetamide dimethylacetal in refluxing anhydrous ethanol leads to intramolecular cyclocondensation to produce substituted pyridothienopyrimidines, viz., 5H-1-thia-3,5,8-triazaacenaphthenes, in good yields. Amidine derivatives were the major products in the case of the coupling of aminothienopyridines with dimethylformamide dimethylacetal under the same conditions. A new approach to the synthesis of substituted pyridothienopyrimidines, viz., 3H-1-thia-3,5,8- triazaacenaphthylenes, based on the prolonged heating of methyl 4-arylamino-3-[1-(dimethylamino)ethylidene]aminothieno[2,3-b] pyridine-2-carboxylates in the excess of acetic anhydride was elaborated. Putative mechanisms of the processes concerned are given. © 2010 Springer Science+Business Media, Inc.


Granik V.G.,Center for Drug Chemistry
Russian Chemical Bulletin | Year: 2010

The present review covers general aspects related to the metabolism of organic compounds, primarily, of biologically active azaheterocycles used as drugs. Compounds of this type occupy a dominant place among known drugs. Data on the main chemical processes determining the pathways of principal biotransformations, such as redox reactions, hydrolysis, alkylation, acylation, various conjugations, isomerizations, and condensations, are summarized. The metabolisms of heterocycles is considered based on the ring size of the substrate. © 2010 Springer Science+Business Media, Inc.

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