E. G. Galkin

Synthesis and specific nootropic activity of (–)-cytisine derivatives with carbamide and thiocarbamide moieties in their structure

N-(methylcytisinyl)-N′-substituted ureas, N-substituted cytisine-12-carbamides, and cytisine-12-thiocarbamide were prepared by reaction of (–)-cytisine with urea and thiourea and of (–)-cytisine and its 12-N-methyl-3-amino derivative with isocyanates. Their specific nootropic activity was studied in vivo. The therapeutic index was determined for the lead compound. Promising candidates for further pharmacological testing were found.

Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII. Investigation of transformations of peroxide products of olefins ozonolysis treated with hydroxylamine hydrochloride

Hydroxylamine hydrochloride efficiently reduces peroxide products of olefins ozonolysis into carbonyl compounds. Depending on the substrate character, solvent, and the treatment conditions the arising aldehydes transformed along the route aldehyde→aldoxime→nitrile→ester into individual compounds or their mixtures, or give the corresponding acetals.

Isolation and GC-MS determination of flavonoids from Glycyrrhiza glabra root

Components of the ethylacetate extract of Glycyrrhiza glabra root were separated based on their acid-base properties. The major components of the fraction soluble in aqueous NaOH were identified by GC-MS as glabridin, the principal component of the ethylacetate extract of licorice root (Glycyrrhiza glabra L.), 4-O-methylglabridin, and hispaglabridin B. The isoflavene glabrin was identified in addition to the isoflavan derivatives.

Synthesis of macrolides with N-containing (azine or hydrazide) groups

Potentially useful 17-, and 22÷25-membered macrolides containing azine or hydrazide groups were synthesized from tetrahydropyran via [1+1]-condensation at room temperature of 7-oxooctyl-7-oxooctanoate, which was obtained via Tishchenko reaction from 7-oxooctanal, with hydrazine hydrate and hydrazides of several dicarboxylic acids.

The kinetic regularities, products, and mechanism of the thermal decomposition of dimethyldioxirane. The contribution of molecular and radical reaction channels

The products and kinetics of the thermal decomposition of dimethyldioxirane (DMDO) were studied. The reaction proceedsvia three parallel pathways: isomerization to methyl acetate, oxygen atom insertion into the C−H bond of a solvent molecule (acetone), and the solvent-induced homolysis of the O−O bond in the DMDO molecule. The contribution of the latter reaction channel isca. 23% at 56°C. The overall kinetic parameters of DMDO thermolysis in oxygen atmosphere were determined. The free radical-induced DMDO decomposition occurs in an inert atmosphere. The formal kinetics of this reaction was investigated. The mechanism of the DMDO thermolysis is discussed.

Lipids, lipophilic components, and biologically active fractions of Viburnum opulus L. seeds.

Methyl and triterpenyl fatty-acid esters and triterpenic acids are isolated and identified from seeds ofViburnum opulus(Caprifoliaceae). The biological activity of pigments and proteins is determined

Activity of Thermopsis schischkinii Alkaloids Against Influenza A(H1N1)pdm09 Virus

Influenza is an acute viral infection that can easily become a pandemic because of the rate of spread and characteristic high percentage of lethal outcomes [1]. As a rule, chemotherapy agents play a decisive role in such epidemic situations so that the development of effective anti-influenza agents with new mechanisms of antiviral activity remains crucial and has become a worldwide trend for drug discovery in general [2, 3]. Agents of plant origin, including quinolizidine alkaloids, are being extensively examined [4–7]. The goals of the present work were to screen the anti-influenza activity of alkaloids from Thermopsis schischkinii (Fabaceae), which is broadly distributed in the Republic of Bashkortostan (RB), to isolate total alkaloids from the plant, to separate them into fractions, and to identify the pure active compounds. Such an approach was used in research in a similar area [8]. Furthermore, the activity of T. schischkinii alkaloids against influenza A(H1N1) virus has not yet been studied. The aerial part of T. schischkinii that was collected during flowering in the middle of May 2014 under normal conditions for the Sibaisky District of RB was studied. The species was defined by Dr. Biol. Sci. N. I. Fedorov (Ufa Institute of Biology, RAS). A herbarium specimen of T. schischkinii was preserved in the herbarium at IB, USC, RAS (No. 147-2014). Plants were cut 7–10 cm from the base, immediately cut into sections (3–5 cm), and dried in the shade at 20–25°C. Ground air-dried raw material (100 g) was extracted by infusion of aqueous Me2CO (1:9) until a silicotungstic acid test was negative. Total alkaloids were extracted as the free bases using the classical method [9]. Column chromatography used standard silica gel 60 (0.05–0.1 mm, Macherey-Nagel, Germany). GC-MS was recorded using a Thermo Finnigan MAT95XP instrument with electron-impact ionization at 70 eV, injector temperature 250°C, HP-5ms column (30 m 0.25 mm), stationary phase thickness 0.25 m, and temperature regime 120°C (initial, 3 min) and 250°C (isothermal, 10 min). Mixture constituents were identified using total mass spectra and library GC-MS data and the AMDIS (Automated Mass Spectral Deconvolution and Identification System) data processing system [10] and were also confirmed using the reference alkaloids (–)-cytisine, thermopsine, pachycarpine, and anagyrine that were isolated by us earlier [11, 12]. Chromatographic peak areas were normalized internally without using correction factors with the total peak areas of the constituents taken as 100% for quantitative analysis. The yield of all alkaloids isolated from the aerial part of T. schischkinii was 1.6 g (1.6% of the air-dried raw material mass). Six sequential fractions, the alkaloid compositions of which were determined by GC-MS, were obtained after separation of total alkaloids by gradient column chromatography over SiO2 [eluent polarity increasing from CHCl3 to CHCl3–MeOH (7:1), and finally MeOH]. The principal constituents of total alkaloids from T. schischkinii were pachycarpine, (–)-cytisine, thermopsine, anagyrine, N-formylcytisine, and argentamine, the last two of which were observed earlier in T. turcica, T. chinensis, and T. alterniflora [13–17] (Table 1).

Oxidation and reduction of 1,1′-[3-(methylsulfanylmethyl)tetrahydro-2H-thiopyran-3,5-diyl]diethanone

Oxidation of 1,1′-[3-(methylsulfanylmethyl)tetrahydro-2H-thiopyran-3,5-diyl]diethanone with equivalent amounts of potassium iodate in glacial acetic acid and hydrogen peroxide in tetrahydrofuran and chloroform gave the corresponding mono- and disulfoxides and disulfone, respectively. Reactions of the title compound with sodium tetrahydridoborate and hydroxylamine hydrochloride afforded mono- and dihydroxy derivatives and monooxime, respectively.

Synthesis from L-menthol of optically active macrolides with N-containing (azine or hydrazide) groups

Potentially useful 15- and 20-membered macrolides containing azine or hydrazide groups were synthesized from L-menthol via [1+1]-condensation at room temperature of 3R,7-dimethyl-6-oxooctyl-3R,7-dimethyl-6-oxooctanoate, which was obtained from 3R,7-dimethyl-6-oxooctanal via a Tishchenko reaction, with hydrazine hydrate or malonic acid dihydrazide.

Convenient synthesis of 5-benzyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one and some its reactions

Abstract5-Benzyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one was synthesized by reaction of 1,2,3,4-tetrachloro-5,5-dimethoxycyclopentadiene with benzyl alcohol in methylene chloride in the presence of powdered sodium hydroxide and benzyltrimethylammonium chloride as phase-transfer catalyst. Deprotection of the title compound gave 2-benzyl-2,4,5-trichlorocyclopent-4-ene-1,3-dione which was subjected to unusual intramolecular carbocyclization initiated by molecular iodine.