Vladimir V. Baranov

Neuroprotective Activity of (+)-(S)-2-[(1S,5R)-(3,7-Dioxo-2,4,6,8-Tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid

A study of the neurotropic, neuroprotective, and antioxidant action of the enantiomers and racemate of 2-[(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid synthesized in a stereoselective reaction of (R)-, (S)-, or (R,S)-N-carbamoylmethionine with 4,5-dihydroxyimidazolidine-2-one showed that only (+)-(S)-2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid had neuroprotective properties. X-ray structure analysis showed that the predominating racemate of glycolurils is crystallized from aqueous solutions as a conglomerate. Antioxidant activity was not detected.

α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols

Acid-catalyzed reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in methanol or propan-2-ol led to the formation of previously unknown ω-(4,6-dialkyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)alkanoic acids and their methyl and isopropyl esters. The structure of some esters was proved by X-ray analysis. Methyl (4,6-diethyl-2-oxo-3a,6adiphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate showed anxiolytic effect.

Diastereoselective synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and their structure

Studies on the synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) based on the condensation of ureas or thioureas with glyoxal or 1,2-dioxo-1,2-diphenylethane showed high diastereoselectivity in the formation of racemates (trans-diastereomers) of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and meso-forms (cis-diastereomers) of 4,5-dihydroxy-4,5-diphenyl-1,3-dialkylimidazolidine-2-thiones; plausible mechanisms of their formation were suggested. X-ray diffraction studies confirmed structures of diastereomers for separate examples of racemates and meso-forms of 4,5-dihydroxyimidazolidin-2-ones (-thiones).

Heliospheric ENA Fluxes: How Sensitive are they to the Ionization State of LIC?

We explore the sensitivity of the fluxes of heliospheric energetic neutral atoms (ENA) at 1 AU to the ionization state of the local interstellar cloud (LIC). The solar wind plasma is compressed and heated in the termination shock transition. The shocked solar plasma is convected toward the heliospheric tail in the heliosheath, the region between the termination shock and the heliopause. The ENAs are produced in charge exchange of the plasma protons and background neutral gas and can be readily detected at 1 AU. The expected ENA fluxes depend on the shocked plasma density, temperature, and velocity in the heliosheath. The size and structure of the heliospheric interface region depend on the parameters of the interstellar medium. ENA fluxes would thus reveal the LIC parameters. We demonstrate the sensitivity of the heliospheric ENA fluxes to the ionization state of the LIC. The axi-symmetric model of the solar wind/LIC interaction includes the self-consistent treatment of the plasma-gas coupling and Monte Carlo simulations of the neutral gas distribution.

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Generally applicable methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones reported from 1923 to 2014 have been reviewed and presented to the attention of chemists in various fields.

Regioselective Synthesis of 1,5-Diaryl-2-(Hydroxyalkyl)-8-Methylglycolurils

The cyclocondensation of N-methylurea with derivatives of tetrahydroimidazooxazolone, tetrahydro-imidazooxazinone, dihydroimidazooxazinone, and tetrahydroimidazooxazepinone was studied for the first time. It was shown that the reactions take place with high regioselectivity, are regular in character, and lead to the formation of previously inaccessible 1,5-diaryl-2-(hydroxyalkyl)-8-methylglycolurils with high yields.

α-Thioureidoalkylation of functionally substituted ureas: II. Synthesis of thio analogs of N-hydroxyalkyl-1,5-diphenylglycolurils

Reactions of N-(hydroxyalkyl)ureas with 4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones gave previously unknown 4,6-dialkyl-1-hydroxyalkyl-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-2-ones which may be regarded as thio analogs of N-(hydroxyalkyl)glycolurils.

Features of self-organization of highly dilute solutions of (S)-, (R)-, and (SR)-methionines and related carbamides and glycolurils

Aqueous solutions of (S)-, (R)-, and (SR)-methionines (1–3); carbamide (4); (S)-, (R)-, and (SR)-N-carbamoylmethionines (5–7); glycoluril (8); and glycolurils containing (S)and (R)-methionine moieties (9 and 10) kept under natural and hypoelectromagnetic conditions were studied in comparison by a complex of physicochemical methods (dynamic and electrophoretic light scattering, conductometry, pH-metry, and dielcometry). The process of selforganization and the properties of dilute solutions (1.0•10–15–10–1 mol L–1) of compounds 1–10 was shown for the first time to depend substantially on the structure of the solute and configuration of methionine (Met) enantiomers. In the series 1–3, the greatest ability to self-organization is observed for solutions of (SR)-Met in which supramolecular domains (1.0•10–5–1.0•10–1 mol L–1) and nanoassociates (1.0•10–11–1.0•10–8 mol L–1) are formed. The formation of nanoassociates in a concentration range of 1.0•10–12–1.0•10–6 mol L–1 can be responsible for the appearance of nonmonotonic concentration dependences of the physicochemical properties of solutions of N-carbamoylmethionines 5–7, whereas the physicochemical properties are more pronounced in solution of (S)-N-carbamoylmethionine 5 than in solutions of 6 and 7. The strongest influence of the configuration of the Met enantiomer on the ability of solution to self-organization was revealed in a series of glycolurils 9, 10: solutions of 9 with the (S)-Met moiety are disperse systems in which nanoassociates are formed in a range of 1.0•10–15–1.0•10–5 mol L–1, whereas in solutions of 10 with the (R)-Met fragment the ability to self-organization in the low-concentration range is absent.

Glycolurils in α-ureido- and α-aminoalkylation Reactions. 3**. N -(hydroxymethyl)glycolurils in Reactions with Aliphatic Amines and Amino Acids*

The condensation of aliphatic alkylamines and achiral amino acids with 1,5-butano-2,4,6,8-tetra-(hydroxymethyl)- and 2,4,6,8-tetra(hydroxymethyl)glycolurils was used to prepare and characterize polycyclic condensed compounds (including some previously unknown examples) containing glycoluril and alkylamine fragments. X-ray structural study of the obtained compounds was used to identify n(N)→σ(C–H) anomeric interaction.

Glycolurils in the synthesis of fused polyheterocyclic compounds

We present a comprehensive analysis of data published over the last decade about the methods applicable to the synthesis of fused polyheterocyclic compounds on the basis of glycolurils.