Showing papers by "Tolstikov Genrikh A published in 2014"
TL;DR: Methyl 1,4-dihydroxyiminodihydroquinopimarate showed both a potent and broad spectrum of cytotoxic activity against NSC lung cancer, colon cancer, breast cancer, renal cancer and leukemia and revealed in vivo antineoplastic activity towards mouse solid transplantable mammary carcinoma Ca755 and colon adenocarcinoma AKATOL.
31 citations
TL;DR: Bioassays using murine macrophage-like and tumor cells show that compound 4, which differs from Soloxolone methyl by the absence of a 9(11)-double bond in the C-ring, displays anti-inflammatory and inhibitory activities with respect to tumor cells with a high selectivity index value.
24 citations
TL;DR: 3-Deoxy-3a-homo-3-aza derivatives of betulin and erythrodiol have been synthesized from betulonic and oleanonic acids.
Abstract: 3-Deoxy-3a-homo-3a-aza derivatives of betulin and erythrodiol have been synthesized from betulonic and oleanonic acids. 3-Deoxy-3a-homo-3a-aza-28-hydroxy-12(13)-oleanene showed the highest antineoplastic activity of the broad spectrum in vitro; the results of an extensive examination of the derivative in vitro enable one to recommend it for in vivo tests. The modification of the compound in the position C28 by the introduction of a methoxycinnamoyl fragment led to the loss of the antineoplastic activity. As a whole, 3-deoxy-3a-homo-3a-aza derivatives of betulin [3-(aminopropyl)-, 28-(2-carboxyethyl)carboxy-, and 28-cinamoyloxy-] exhibited a moderate antineoplastic activity toward large intestine cancer, breast cancer, and leukemia cells.
23 citations
TL;DR: The application of water as the solvent component favors the increase in the fraction of nitrogen-containing organic compounds (semicarbazones, keto-and aldoximes, nitriles) and reduction in the yield of carboxylic acids as discussed by the authors.
Abstract: Hydrochlorides of hydroxylamine and semicarbazide efficiently reduce peroxide products of olefin ozonolysis in a system CH2Cl2-AcOH leading to the formation of carboxylic acids and their derivatives. The application of water as the solvent component favors the increase in the fraction of nitrogen-containing organic compounds (semicarbazones, keto- and aldoximes, nitriles) and reduction in the yield of carboxylic acids.
9 citations
TL;DR: Griesbaum ozonolysis of mixtures of methyl 3-(methoxyimino)-5β-cholan-24-oate with ketones (cyclohexanone, methyl trifluoromethyl ketone, and phenyl triflormethemethyl ketone) enabled for the first time steroidal 1,2,4-trioxolanes which were isolated as mixtures OF stereoisomers as mentioned in this paper.
Abstract: Griesbaum ozonolysis of mixtures of methyl 3-(methoxyimino)-5β-cholan-24-oate with ketones (cyclohexanone, methyl trifluoromethyl ketone, and phenyl trifluoromethyl ketone) afforded for the first time steroidal 1,2,4-trioxolanes which were isolated as mixtures of stereoisomers.
7 citations
TL;DR: It was found that single intraperitoneal administration of any compound followed by 30-min ischemia and 120-min reperfusion resulted in statistically significant decrease of myocardial infarct area.
Abstract: Cardioprotective effect of resveratrol and resveratroloside was determined in ischemia-reperfusion experiments on rats. It was found that single intraperitoneal administration of any compound (10 mg/kg) followed by 30-min ischemia and 120-min reperfusion resulted in statistically significant decrease of myocardial infarct area (55.0±4.0% for control group; 40.7±4.4% for the group 1 received resveratrol; 41.6±4.8% for the group 2 received resveratroloside). The cardioprotective effect of resveratroloside was detected for the first time.
7 citations
TL;DR: In this article, the anti-inflammatory activity of amides of levopimaric acid (LpA) with acetylenic moiety and its esters with 4-R-triazolic substitutions was investigated using histamine-induced mice paw edema model.
Abstract: Anti-inflammatory activity of amides of levopimaric acid (LpA) with acetylenic moiety and its esters with 4-R-triazolic substitutions was investigated using histamine-induced mice paw edema model. The synthesized LpA derivatives possess anti-inflammatory activity comparable to the activity of indomethacin.
6 citations
TL;DR: In this paper, the authors report on new versions of this reaction by the examples of adamantanolactone (XII), β-campholide (XIII), caranolactones (XIV), and also allobetulonolactone(XV) and norallobetsalactones(XVI) obtained from betulin.
Abstract: Here we report on new versions of this reaction by the examples of adamantanolactone (XII), β-campholide (XIII), caranolactone (XIV), and also allobetulonolactone (XV) and norallobetulonolactone (XVI) obtained from betulin [3]. At the reduction of adamantanolactone (XII) isobutylacetal (VII) formed in 60% yield. β-Campholide (XIII) afforded a diastereomeric mixture (58 : 42 according to Н NMR data) of acetal VIII. In the stereochemical assignment of the NMR spectra of compound VIII the chemical shift values of the bridgehead carbon atoms (С, С) and those in the bottom of the boat (С, С), and also the chemical shifts and coupling constants of the anomeric proton Н are informative. Relatively downfield signals of the mentioned atoms С (~δ 1–2.5 ppm), and also more upfield shift of the anomeric proton Н at 5.06 ppm and a large value of J3,4 5.3 Hz indicate the equatorial orientation of the i-BuО group in the prevailing stereoisomer. According to Н NMR data compound IX formed as a mixture (3 : 1) of epimers with respect to asymmetric acetal center. The value J2,3 8.9 Hz of the anomeric proton in the predominant stereoisomer indicates its axial orientation and consequently the equatorial position of the isobutoxy group.
5 citations
TL;DR: In this article, p-(pent-4-enyloxy)aniline with salicylaldehyde containing versatile substituents in the positions 3 and 5 in an open system without solvent at 130°C afforded a series of (N-aryl)salicylaldimines, which with TiCl2(OPr-i)2 formed complexes of titanium(IV) dichloride L2TiCl2
Abstract: Reactions of p-(pent-4-enyloxy)aniline with salicylaldehyde containing versatile substituents in the positions 3 and 5 in an open system without solvent at 130°C afforded a series of (N-aryl)salicylaldimines, which with TiCl2(OPr-i)2 formed complexes of titanium(IV) dichloride L2TiCl2
5 citations
TL;DR: Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives as mentioned in this paper.
Abstract: Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives.
5 citations
TL;DR: In this paper, the reaction of 5-methoxy-substituted salicylic aldehydes containing in the position 3 tert-butyl, 2-phenylpropan-2-yl, or 1-phenylethyl groups with m- and p-allyloxy-, (but-3-enyloxy)-, (pent-4]-anilines without solvent in an open system at 130°C afforded a series of (N-aryl)salicylaldimines L that with TiCl2 (OPr
Abstract: Reaction of 5-methoxy-substituted salicylic aldehydes containing in the position 3 tert-butyl, 2-phenylpropan-2-yl, or 1-phenylethyl groups with m- and p-allyloxy-, (but-3-enyloxy)-, (pent-4-enyloxy)anilines without solvent in an open system at 130°C afforded a series of (N-aryl)salicylaldimines L that with TiCl2 (OPr-i)2 formed complexes of titanium(IV) dichloride L2TiCl2.
TL;DR: In this paper, Ozonolytic transformations of 10-undecenoic acid, which is available from castor oil, were studied and several α, ω-bifunctional sebacic acid derivatives were developed.
Abstract: Ozonolytic transformations of 10-undecenoic acid, which is available from castor oil, were studied. Syntheses of several α, ω-bifunctional sebacic acid derivatives were developed.
TL;DR: The main methods for the synthesis of derivatives of A-seco pentacyclic triterpenoids by means of the Baeyer-Villiger reaction, the Beckmann rearrangement, and other oxidation processes are reviewed in this paper.
Abstract: The review considers the main methods for the synthesis of derivatives of A-seco pentacyclic triterpenoids by means of the Baeyer-Villiger reaction, the Beckmann rearrangement, and other oxidation processes.
TL;DR: In this paper, peroxide products of partial ozonolysis of (S)-(-)-limonene (ee 50%) in cyclohexane-methanol at 2-4°C were treated with a solution of HCl in methanol, which led to the formation of a 4: 1 mixture of methyl [(1S)-2,4-dimethoxy-2, 4-dimethylcyclohexyl]acetate and [(1 S)-2.4]-dimethoxyl]-acetaldehyde, each being represented by a single pair
Abstract: Peroxide products of partial ozonolysis of (S)-(-)-limonene (ee 50%) in cyclohexane-methanol at 2–4°C were treated with a solution of HCl in methanol, which led to the formation of a 4: 1 mixture of methyl [(1S)-2,4-dimethoxy-2,4-dimethylcyclohexyl]acetate and [(1S)-2,4-dimethoxy-2,4-dimethylcyclohexyl]acetaldehyde, each being represented by a single pair of diastereoisomers at a ratio of 3: 1.
TL;DR: In this article, a review summarizes the research results and application aspects of the original series of trichlorocyclopentenones synthesized from hexachlorocyCLopentadiene.
Abstract: The review summarizes the research results and application aspects of the original series of trichlorocyclopentenones synthesized from hexachlorocyclopentadiene.
TL;DR: In this paper, a reduction agent for peroxide products of ozonolysis of olefins with different degrees of substitution was proposed. But the reduction agent was ineffective.
Abstract: Hydroxylamine and semicarbazide hydrochlorides are found to be effective reducing agents towards peroxide products of ozonolysis of olefins with different degrees of substitution.
TL;DR: In this paper, methods for functionalization of some plant metabolites or their derivatives, viz., the eudesmane-type methylidenelactones, diterpene and morphinane alkaloids, furanolabdanoids, lupanes triterpenoids, and coumarins, using the metal complex catalysis, are reviewed.
Abstract: Developed by the authors methods for the functionalization of some plant metabolites or their derivatives, viz., the eudesmane-type methylidenelactones, diterpene and morphinane alkaloids, furanolabdanoids, lupanes triterpenoids, and coumarins, using the metal complex catalysis, are reviewed.
TL;DR: Ozonolysis of (1R, 3R)-p-menth-4-en-3-ol in methylene chloride or methanol in the presence of pyridine afforded a mixture of equimolar amounts of epimeric 1]-(2R, 4S, 6S)- and 1-[(2S, 4s,6S)-6-hydroxy-4methyltetrahydro-2H-pyran-2-yl]-2-methylpropan-1-ones as discussed by the authors.
Abstract: Ozonolysis of (1R,3R)-p-menth-4-en-3-ol in methylene chloride or methanol in the presence of pyridine afforded a mixture of equimolar amounts of epimeric 1-[(2R,4S,6S)- and 1-[(2S,4S,6S)-6-hydroxy-4-methyltetrahydro-2H-pyran-2-yl]-2-methylpropan-1-ones. A probable reaction mechanism is discussed.