Showing papers by "Tolstikov Genrikh A published in 2010"
TL;DR: According to the results of antiviral screening against human papillomavirus type 11 the selectivity index for tested triterpenoids has a range from 10 to 35 with no cellular cytotoxicity, the most remarkable activity was found for 3beta,28-di-O-nicotinoylbetulin.
67 citations
TL;DR: In this article, the properties of dihydroquinopimaric acid methyl ester and its derivatives with dimethyldioxirane were confirmed by X-ray crystallographic analysis and they were found to be moderately active against influenza virus type A and the papilloma virus.
27 citations
TL;DR: New effective compounds such as maleopimaric acid and its methyl ether, a product of ozonolysis—diterpenic secotriacid—and maleopamaric acid amide with L-leucine were found.
Abstract: The synthesis of a new group of maleopimaric acid amides containing fragments of methyl ethers of amino acids, aliphatic amines, imidazole, and N-methylpiperazine was carried out. The ozonolysis of methylmaleopimarate occurs via the cleavage of the double bond C18(19) and the opening of an anhydrous ring with the formation of secotriacid. As a result of the screening of the anti-inflammatory and antiulcer activity of maleopimaric acid derivatives, new effective compounds such as maleopimaric acid and its methyl ether, a product of ozonolysis—diterpenic secotriacid—and maleopimaric acid amide with L-leucine were found. An important advantage of the studied compounds is the low toxicity and the presence of bidirectional activity in the absence of adverse effects on the animal.
25 citations
TL;DR: In this paper, N-methylpyperazinyl amides of betulinic, platanic, glycyrrhetic, oleanolic, ursolic, and moronic acids were synthesized and modified.
Abstract: N-methylpyperazinyl amides of betulinic, platanic, glycyrrhetic, oleanolic, ursolic, and moronic acids were synthesized and modified. Betulin and betulonic acid showed antimicrobial activity against Staphylococcus aureus at a concentration of 90 mg/ml, and betulin manifested a bacteriostatic effect against Klebsiella pneumoniae at a concentration of 60 mg/ml. Among the studied N-methylpyperazinyl amides, the highest activity against S. aureus was observed for a betulonic acid derivative.
25 citations
TL;DR: In this paper, the main laws of olefin ozonolysis and further transformation of the peroxide products in splitting reactions and at the treatment with oxidants and reducers are summarized.
Abstract: The review summarizes the main laws of olefin ozonolysis and also further transformation of the peroxide products in “splitting” reactions and at the treatment with oxidants and reducers.
24 citations
TL;DR: Using a carrageenan inflammation model, it is demonstrated that the anti-inflammatory activity of quinopimaric acid derivatives was comparable with that of diclofenac.
Abstract: Under the action of PCl5, the Beckman rearrangement of a 3: 1 mixture of Z- and E-isomeres of 18β-hydro-xydihydroquinopimaric acid resulted in 5′-caprolactam and isomeric caprolactams containing fragments of cyclic ether. Z- and E-ketoximes were separated as acetates. Using a carrageenan inflammation model, we demonstrated that the anti-inflammatory activity of quinopimaric acid derivatives was comparable with that of diclofenac.
22 citations
TL;DR: The synthesis of a new group of triterpenoid acylates has been conducted on the basis of oleanolic, glycyrrhetic, and ursolic acids and betulin to possess high activity against the influenza type A (H1N1) virus and the papilloma virus.
Abstract: The synthesis of a new group of triterpenoid acylates has been conducted on the basis of oleanolic, glycyrrhetic, and ursolic acids and betulin. 28-ortho-Methoxycynnamoylbetulin has been demonstrated to possess high activity against the influenza type A (H1N1) virus with the selectivity index SI > 100 while studying the activity of the synthesized compounds in relation to the reproduction of viral pathogens of respiratory infections. The high activity of 3,28-dinicotinoylbetulin against the papilloma virus (strain HPV-11) was detected with the selectivity index SI 35.
20 citations
TL;DR: By Heck reaction of isoalantolactone with bromides or aryl iodides, products of the double bond shift, were synthesized as discussed by the authors, and the yields of the arylation products depend on the nature of the catalytic system and on the structure of the bromide.
Abstract: By Heck reaction of isoalantolactone with aryl bromides or aryl iodides (3aR,4aS, 8aR,9aR,E)-3-arylmethylidene-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-ones and (4aS,8aR,9aS)-3-arylmethyl-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-ones, products of the double bond shift, were synthesized. The yields of the arylation products depend on the nature of the catalytic system and on the structure of the aryl halide. The structures of (3aR,4aS,8aR,9aR,E)-3-(3,4-dimethoxybenzylidene)-8amethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one and (4aS,8aR,9aS)-3-(2-methylsulfanylbenzyl)-8amethyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one were proved by XRD analysis.
16 citations
TL;DR: In this paper, four triterpenoids with alkyne moieties have been synthesized by the proposed procedure; among them, 3β,28-dihydroxy-29-norlup-20(30)-yne has demonstrated antiviral activity against papilloma virus and HCV replicon.
15 citations
TL;DR: This study has demonstrated that the polysaccharide arabinogalactan (AG), which is ametabolite of the endemics of Siberian forest floralarches, is an important component of glycosides of higher terpenoids.
Abstract: The ability of the carbohydratecontaining naturalmetabolites to bind drugs by formation of complexes(clathration) attracts attention because this allows thepharmacon dose and toxicity to be reduced, with theirpleiotropic properties improved and the basic effectretained.We demonstrated previously that this ability wascharacteristic of glycosides of higher terpenoids, suchas glycyrrhizinic acid [1, 2], stevioside, and rebaudioside [3].In this study, we have demonstrated that thepolysaccharide arabinogalactan (AG), which is ametabolite of the endemics of Siberian forest floralarches
12 citations
TL;DR: New olean-18(19)-ene triterpenoids were effectively synthesized by the interaction of allobetulin or its acetate with phosphorous oxychloride in refluxing pyridine.
Abstract: New olean-18(19)-ene triterpenoids were effectively synthesized by the interaction of allobetulin or its acetate with phosphorous oxychloride in refluxing pyridine. The structures of the synthesized 17-chloromethyloleane-18(19)-enes were confirmed by NMR spectroscopy and X-ray analysis.
TL;DR: In this paper, the Vilsmeier-Haak reaction of phlomisoic acid methyl ester gave a mixture of 15- and 16-formyllabdanoids.
Abstract: Vilsmeier-Haak reaction of phlomisoic acid methyl ester gave a mixture of 15- and 16-formyllabdanoids. In addition, methyl 2-formyldodecahydrophenanthro[1,2-b]furan-6-carboxylate was isolated, and its structure was determined by X-ray analysis. Reductive amination of 16-formyllabdanoid with benzylamine or α-amino acid methyl esters led to the formation of labdanoid furfurylamines which reacted with maleic anhydride to produce N-substituted 4-oxo-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-ene-6-carboxylic acids. Acylation of labdanoid furfurylamines with (E)-but-2-enoyl chloride afforded the corresponding unsaturated amides which were converted into 10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-en-4-ones via intramolecular Diels-Alder reaction. Treatment of the oxa adducts with boron trifluoride-diethyl ether complex gave dihydroisoindol-1-one derivatives containing a diterpene fragment.
TL;DR: In this article, a method for preparing methyl esters of 12-oxoolean-28-oic and 3,12-dioxoolean 28-Oic acids via ozonolysis of oleanolic acid methyl ester in CH2Cl2 at -60°C was proposed.
Abstract: A method for preparing methyl esters of 12-oxoolean-28-oic and 3,12-dioxoolean-28-oic acids via ozonolysis of oleanolic acid methyl ester in CH2Cl2 at –60°C was proposed. It was found that oxidation of 2-cyano3,4-seco-4(23)-oleanenoic acid was chemoselective depending on the amount of ozone used.
TL;DR: In this article, the main reaction paths were found to be oligomerization and isomerization of sabinene with crotonaldehyde, which gave rise to several polyfunctional heterocyclic compounds.
Abstract: Transformations of sabinene catalyzed by montmorillonite K10 clay were studied. The main reaction paths were found to be oligomerization and isomerization. The reaction of sabinene with crotonaldehyde gave rise to several polyfunctional heterocyclic compounds.
TL;DR: A method for preparing 15,16-epoxylabda-8(9),13,16,14-trien-18-oic (phlomisoic) acid was proposed in this article.
Abstract: A method for preparing 15,16-epoxylabda-8(9),13(16),14-trien-18-oic (phlomisoic) acid was proposed. Its structure was confirmed by an XSA. N-containing derivatives of phlomisoic acid that contained amines, hydrazides, and methyl esters of amino acids on the C-18 atom in addition to (2-oxo-2-aminoacetyl)-substituted derivatives of the C-16 methyl ester of phlomisoic acid were prepared.
TL;DR: An effective method for preparing triterpene 2,3-seco-2,3diacids by ozonolysis of 2-exomethylene-substituted derivatives of betulonic acid and 28-oxoallobetulone was proposed in this paper.
Abstract: An effective method for preparing triterpene 2,3-seco-2,3-diacids by ozonolysis of 2-exomethylene-substituted derivatives of betulonic acid and 28-oxoallobetulone was proposed.
TL;DR: A new triterpenoid of the germanicane series 3S,19R-diacetoxy-17-iodomethylenoleanane has been synthesized by treating allobetulin with acetyl chloride and sodium iodide in acetonitrile.
Abstract: A new triterpenoid of the germanicane series 3S,19R-diacetoxy-17-iodomethylenoleanane has been synthesized by treating allobetulin with acetyl chloride and sodium iodide in acetonitrile. The structure of the compound obtained has been corroborated by X-ray analysis data.
TL;DR: In this paper, lossen rearrangement of N-hydroxymaleopimaric acid amide p-toluenesulfonate in the presence of amines in methanol led to the formation of the corresponding diterpene ureido esters with high regio-and stereoselectivity.
Abstract: Lossen rearrangement of N-hydroxymaleopimaric acid amide p-toluenesulfonate in the presence of amines in methanol led to the formation of the corresponding diterpene ureido esters with high regio- and stereoselectivity. Treatment of the resulting ureides with phosphoryl chloride gave cyclic amidines via intramolecular ring closure. Substituted hydantoins were obtained by reactions of the ureido esters with glyoxal in acid medium, and their treatment with sodium ethoxide in ethanol afforded compounds of the naphtho[1,2-h]-quinazoline series.
TL;DR: In this article, a series of corresponding diimines that at treating with TiCl2(OPr-i)2 formed mono-and binuclear complexes of titanium(IV) dichloride with tetradentate ligands LTiCl2 and L2(TiCl2)2.
Abstract: Reactions of 2-hydroxy-1-naphthaldehyde with 1,4-diaminobutane, 1,6-diaminohexane, 4,4′-methylenedianiline and its alkyl- and cycloalkyl-sybstituted derivatives, with 4,4′-sulfonyldianiline, 2,2′- and 4,4′-oxydianiline, 4,4′-(1,4-phenylenebisoxy)dianiline, 4,4′-[propane-2,2-diylbis(1,4-phenylenebisoxy)]dianiline, and p-terphenyl-4,4″-diamine afforded a series of the corresponding diimines that at treating with TiCl2(OPr-i)2 formed mono- and binuclear complexes of titanium(IV) dichloride with tetradentate ligands LTiCl2 and L2(TiCl2)2.
TL;DR: In this paper, a regioselective [4+2]-cycloaddition of coumarin-3-carboxylic acids to 2-(3-trimethylsiloxybuta- 1,3-dien-1-yl)furans was efficiently catalyzed with L-proline.
Abstract: Methods of synthesis were developed for 7-(furan-2-yl)-substituted 7,8,10,10a-tetrahydrobenzo[c] chromen-6,9-diones by regioselective [4+2]-cycloaddition of coumarin-3-carboxylic acids to 2-(3-trimethylsiloxybuta- 1,3-dien-1-yl)furans. The [4+2]-cycloaddition was efficiently catalyzed with L-proline.
TL;DR: In this article, a palladium-catalyzed amination of 2-(1,3-dibromopropan-2-ylidene)-7H-furo[3,2-g]chromene-3,7(2H)-dione with various amines and amino acid derivatives led to the formation of the corresponding 2-( 1, 3-diaminopropano-2,ylidenes)-substituted oreoselones, whose yields depended on the catalytic system, base, and amine structure
Abstract: Palladium-catalyzed amination of 2-(1,3-dibromopropan-2-ylidene)-7H-furo[3,2-g]chromene-3,7(2H)-dione with various amines and amino acid derivatives led to the formation of the corresponding 2-(1,3-diaminopropan-2-ylidene)-substituted oreoselones. The yields depended on the catalytic system, base, and amine structure. Di- and polyazamacrocyclic furocoumarin derivatives were obtained by reactions of 2-(1,3-dibromopropan-2-ylidene)-7H-furo[3,2-g]chromene-3,7(2H)-dione with linear di- and polyamines (hexamethylenediamine, spermine, spermidine, and 3,6-dithiaoctane-1,8-diamine), catalyzed by palladium complexes.
TL;DR: In this paper, reformatsky reaction of 16-formylmethyllambertianate with α-bromoesters of carboxylic acids stereoisomeric β-hydroxyesters of labdanoids were synthesized.
Abstract: Reactions of 16-cyanomethyllambertianate with organozinc reagents obtained from ethyl esters of α-bromoacetic, α-bromopropionic, and α-bromobutyric acids gave the corresponding enaminoesters, β-ketoesters, and β-hydroxyesters of labdanoids whose yield depended on the reaction conditions and the structure of the α-bromoester. By Reformatsky reaction of 16-formylmethyllambertianate with α-bromoesters of carboxylic acids stereoisomeric β-hydroxyesters of labdanoids were synthesized.
TL;DR: The urgent task is to search for new antitumor agents that provide high treatment selectivity and efficacy and the problem of residual tumor clone remains unsolved.
Abstract: Schemes for the treatment of different types of malignant tumors are based on the use of surgical methods combined with highdosage polychemother� apy. A serious flaw of the latter is the high toxicity of contemporary antitumor agents against vital organs and systems of organism. Associated side effects decrease the efficacy and in some cases limit the use of antitumor agents. The problem of residual tumor clone remains unsolved. Tumor cells that survive che� motherapy show drug resistance against a wide range of pharmaceuticals and often cause the recurrence of disease in an even more severe form. Therefore, the urgent task is to search for new antitumor agents that provide high treatment selectivity and efficacy. The use of substances obtained by synthetic trans� formations of plant metabolites, especially those that are known reliably to show biological activity and available at present or in future as a source of raw materials is an important tendency of medicinal chemistry intended for the development of new effi� cient antitumor agents. These types of compounds involve pentacyclic triterpenes whose wide spectrum of pharmacological activity attracts and expands the interest of researchers in these compounds (1-5).
TL;DR: In this paper, a trifluoroacetic acid and a potassium nitrate nitrating mixture were used to synthesize the 5′-bromo-derivative of lappaconitine.
Abstract: Nitro-derivatives of lappaconitine were synthesized for the first time by nitration of the alkaloid and its 5′-bromo-derivative using a trifluoroacetic acid and potassium nitrate nitrating mixture. Reduction of the nitro-derivatives by Sn(II) chloride in HCl produced the corresponding amino-derivatives of N-deacetyllappaconitine.
TL;DR: 3-Deoxy-3β-(3-aminopropoxyamino) derivatives of oleanolic and ursolic acids were synthesized in this article, which was active in vitro with selectivity index SI 30 against the strain HPV-11.
Abstract: 3-Deoxy-3β-(3-aminopropoxyamino) derivatives of oleanolic and ursolic acids were synthesized. 3-Deoxy3-(2-cyanoethoxyimino)urs-12-en-28-oic acid was active in vitro with selectivity index SI 30 against papilloma virus (strain HPV-11).
TL;DR: In this article, the successful application of dimethyldioxirane for selective oxidation of an oxygen-containing tertiary C atom to form a hemiacetal, the preparation of which is inaccessible by other methods, was demonstrated using dihydroquinopimaric acid derivatives as examples.
Abstract: Successful application of dimethyldioxirane for selective oxidation of an oxygen-containing tertiary C atom to form a hemiacetal, the preparation of which is inaccessible by other methods, was demonstrated using dihydroquinopimaric acid derivatives as examples.
TL;DR: In this paper, a new method for the preparation of optically active omeprazole, consisting in asymmetric oxidation of the corresponding sulfide with the use of vanadyl complexes with chiral Schiff bases as the catalysts has been elaborated.
Abstract: A new method for the preparation of optically active omeprazole, consisting in asymmetric oxidation of the corresponding sulfide with the use of vanadyl complexes with chiral Schiff bases as the catalysts has been elaborated. The best results of the oxidation were achieved by the use of the combination VO(acac)2—2-[{(1S,2S,3R,5S)-3-hydroxymethyl-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-ylimino}methyl]phenol—N-ethyl-N,N-diisopropylamine.
TL;DR: In this article, a more convenient alternative procedure for the synthesis of Schiff bases (V) starting from p-aminophenol is presented, which can be used to synthesize Schiff bases starting from Schiff bases.
Abstract: A more convenient alternative procedure for the synthesis of Schiff bases (V) starting from p-aminophenol is presented.