RAS Institute of Organic Chemistry

Oktyabrya, Russia

RAS Institute of Organic Chemistry

Oktyabrya, Russia

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Samsonov V.A.,RAS Institute of Organic Chemistry
Russian Journal of Organic Chemistry | Year: 2017

The reaction of 2,6-bis(hydroxyimino)cyclohexan-1-one with aldehydes and ammonia afforded 2-substituted 4-hydroxyimino-4,5,6,7-tetrahydro-1H-benzimidazol-1-ols which were hydrolyzed to 1-hydroxy- 2-R-1,5,6,7-tetrahydro-4H-benzimidazol-4-ones. The N-hydroxy group in the latter can readily by removed by the action of chloroacetone in the presence of a base (potassium carbonate or triethylamine); as a result, 2-substituted 1,5,6,7-tetrahydro-4H-benzimidazol-4-ones were obtained. © 2017, Pleiades Publishing, Ltd.


Salakhutdinov N.F.,Novosibirsk State University | Laev S.S.,RAS Institute of Organic Chemistry
Bioorganic and Medicinal Chemistry | Year: 2014

This review is the first attempt at systematization of the literature data on the structures and activities of triglyceride-lowering agents which used in medical practice or are in development. The effects and mechanisms of action of statins, squalene synthase inhibitors, fibrates, PPARα and PPARα/γ agonists, nicotinic acid, omega-3 fatty acids and some other molecular targets were considered. Unfortunately, to date, harmless and effective triglyceride-lowering drug still does not exist and there is still need for development of better triglyceride-lowering agents. © 2014 Elsevier Ltd. All rights reserved.


Lathe R.,RAS Institute of Organic Chemistry | Kotelevtsev Y.,Queens Medical Research Institute
Steroids | Year: 2014

Steroid/sterol-binding receptors and enzymes are remarkably promiscuous in the range of ligands they can bind to and, in the case of enzymes, modify - raising the question of how specific receptor activation is achieved in vivo. Estrogen receptors (ER) are modulated by 27-hydroxycholesterol and 5α-androstane-3β,17β-diol (Adiol), in addition to estradiol (E2), and respond to diverse small molecules such as bisphenol A. Steroid-modifying enzymes are also highly promiscuous in ligand binding and metabolism. The specificity problem is compounded by the fact that the steroid core (hydrogenated cyclopentophenanthrene ring system) has several planes of symmetry. Ligand binding can be in symmetrical East-West (rotation) and North-South (inversion) orientations. Hydroxysteroid dehydrogenases (HSDs) can modify symmetrical 7 and 11, also 3 and 17/20, positions, exemplified here by yeast 3α,20β-HSD and mammalian 11β-HSD and 17β-HSD enzymes. Faced with promiscuity and symmetry, other strategies are clearly necessary to promote signaling selectivity in vivo. Gating regulates hormone access via enzymes that preferentially inactivate (or activate) a subclass of ligands, thereby governing which ligands gain receptor access - exemplified by 11β-HSD gating cortisol access to the mineralocorticoid receptor, and P450 CYP7B1 gating Adiol access to ER. Counter-intuitively, the specificity of steroid/sterol action is achieved not by intrinsic binding selectivity but by the combination of local metabolism and binding affinity. © 2014 Elsevier Inc. All rights reserved.


Salakhutdinov N.F.,RAS Institute of Organic Chemistry
Mini reviews in medicinal chemistry | Year: 2010

This review discusses the most active natural and synthetic curarelike compounds demonstrating myorelaxants activity. The data are grouped according to chemical structures, namely, quinoline and isoquinoline myorelaxants, myorelaxants with saturated heterocyclic or alkylamine fragments, myorelaxants with a steroid framework, natural and synthetic alkaloid myorelaxants.


Gataullin R.R.,RAS Institute of Organic Chemistry
Russian Journal of Organic Chemistry | Year: 2013

The review considers new advances in the synthesis of indoles annulated with cycloalkanes. © 2013 Pleiades Publishing, Ltd.


Vlasov V.M.,RAS Institute of Organic Chemistry
New Journal of Chemistry | Year: 2010

Changes of the activation parameters, ΔH‡ and ΔS‡, in the SN2, SNV, Ad N, SNAr and acyl-transfer reactions with phenol, aniline and pyridine nucleophiles in various solvents were correlated with σ constants of the substituents in the aromatic ring of the nucleophiles. The resultant δΔH‡ and δΔS ‡ reaction constants are linearly related for variations of substituents at the nucleophile. Correlation of δΔH ‡vs. δΔS‡ allow the estimation of the contribution of changes of the internal enthalpy, δΔH ‡ int, to the enthalpy reaction constant, δΔH‡, which gives a single linear dependence on the Hammett ρ reaction constants for all bimolecular nucleophilic reactions. The deviations from dependence of δΔH‡ intvs. ρ can be interpreted in terms of changes of the transition state structure or reaction mechanism. The results obtained show that the substituent effects in the nucleophiles on the charge development in the transition state are governed by the magnitude of δΔH ‡ int. © 2010 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.


Vlasov V.M.,RAS Institute of Organic Chemistry
New Journal of Chemistry | Year: 2010

Changes of the activation parameters, ΔH≠ and ΔS≠, in the SN2, SNAr and acyl-transfer reactions with charged and neutral nucleophiles in various solvents were correlated with σ constants of the substituents in the aromatic ring of the substrates. The resultant δΔH≠ and δΔS≠ reaction constants are linearly related for variations of substituents at the substrate. Correlation of δΔH ≠vs. δΔS≠ allows one to estimate the contribution of changes of the internal enthalpy, δΔH≠int, to the enthalpy reaction constant, δΔH≠, which gives a single linear dependence on the Hammett ρ reaction constants for all bimolecular nucleophilic reactions. The deviations from dependence of δΔH≠intvs. ρ can be interpreted in terms of changes of the transition state structure or reaction mechanism. The results obtained show that the substituent effects in the substrates and nucleophiles on the charge development in the transition state are governed by the magnitude of δΔH≠int. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.


Klabunovskii E.I.,RAS Institute of Organic Chemistry
Russian Journal of Organic Chemistry | Year: 2012

The review analyzes factors responsible for the appearance of homochirality in determinate processes, as well as the role of indeterminate processes in the earth biosphere and space and their effect on the biosphere evolution functionality. Modern views on the significance of homochirality for the evolution of earth biosphere are considered. © Pleiades Publishing, Ltd., 2012.


Os'Kina I.A.,RAS Institute of Organic Chemistry
International Journal of Chemical Kinetics | Year: 2014

Transesterification of R-substituted phenyl benzoates 1-5 with 4-methoxyphenol 6 was kinetically investigated in the presence of K 2CO3 in dimethylformamide (DMF) at various temperatures. The Hammett plots for the reactions of the 1-5 demonstrate good linear correlations with σ0 constants. Low magnitude of ρLG values indicate that the leaving group departure occurs after the rate-determining step. The Brønsted coefficient values for the reactions (-0.2, -0.16, -0.13 at 15, 24, 36°C, respectively) demonstrate the weak effect of leaving group substituent on the reactivity of R-substituted phenyl benzoates 1-5 for the reactions with 4-methoxyphenol 6 in the presence of K2CO3 in DMF. The leaving group substituent effect on free energy (ΔG≠), enthalpy (ΔH≠), and entropy (ΔS≠) of activation was examined. It was shown that the activation parameters obtained depend weakly on the leaving group substituent effect. The reaction is entropy controlled in case the leaving group substituent becomes electron withdrawing. © 2013 Wiley Periodicals, Inc.


Variation of the activation parameters in the S N2, acyl-transfer, S NAr, S NV, and Ad N reactions offers a uniquely useful probe for the mechanistic features of these reactions in solution. New approach uses the substituent effects on the aromatic ring to the variation of the activation parameters, ΔH ≠ and ΔS ≠, in the above reactions in the frameworks of the Hammett-like equations in order to evaluate the resultant δΔH ≠ and δΔS ≠ reaction constants. Compensation relationships of δΔH ≠ versus δΔS ≠ allow one to estimate the contribution of changes of the internal enthalpy, δΔH ≠ int, to the enthalpy reaction constant, δΔH ≠, that is inherent to bimolecular nucleophilic reactions and gives a single linear dependence on the Hammett ρ reaction constants for these reactions. The deviations from dependence of δΔH ≠ int versus ρ serve as useful points of interpretation of changes of the transition state structure or reaction mechanism. The results obtained show that the substituent effects in the substrates, nucleophiles, and leaving groups on the mechanistic features in bimolecular nucleophilic reactions are governed by the magnitude of δΔH ≠ int. Copyright © 2011 John Wiley & Sons, Ltd.

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