Елена Клен - Academia.edu (original) (raw)
Papers by Елена Клен
HETEROCYCLES, 1990
Treatment of methyl styrylsulfonylacetate with arenediazonium chlorides gave methyl styrylsulfony... more Treatment of methyl styrylsulfonylacetate with arenediazonium chlorides gave methyl styrylsulfonylglyoxylate arenehydrazones, which were cyclized on treatment with bases to 4-aryl-5-phenyl-5,6-dihydro-1,3,4-thiadiazine 1,1-dioxides, a hitherto unknown class of heterocycles
The reactions of the 2-chlorine substituted thietanylbenzimidazols with hydrazine-hydrate have be... more The reactions of the 2-chlorine substituted thietanylbenzimidazols with hydrazine-hydrate have been investigated. The procedures for synthesis of the 2-ilidenhydrazing of tietanylbenzimidazol and also the procedure for synthesis of the ilidenhydrazides of 2-(benzimidazolyl-2-thio) acetic acids containing the tietan cycle have been developed. The early-unknown salts of the 2-(benzimidazolyl-2-thio) acetic acids containing the tientan cycle have been created. The new tietanylbenzimidazol derivatives displaying the immunodepressive, antioxidant, antiaggression and antimicrobic activities have been synthesized. The developed synthesis procedures and discovered structure - activity regularities are used on the departments of pharmaceutic chemistry and microbiology of the Bashkir State Medical University and at the Institute of Organic Chemistry (Ufa Scientific Centre of Russian Academy of Sciences)Available from VNTIC / VNTIC - Scientific & Technical Information Centre of RussiaSIGLERURu...
Russian Journal of Organic Chemistry, 2014
Kazan medical journal
The article presents the results of systematic studies on the search for new biologically active ... more The article presents the results of systematic studies on the search for new biologically active molecules with antidepressant activity in the series of thietane-containing heterocyclic compounds and 3-substituted thietane dioxides. The used strategy for the search for antidepressant substances, based on in vivo pharmacological screening in combination with in silico methods of mathematical modeling and toxico-pharmacokinetic evaluation, is described. Studies of the biological activity of thietane-containing reaction products of azoles with thiiranes have been carried out in the series of thietanylimidazoles, titanixanthines, thietanyltriazoles, thietanyltriazolones, and 3-substituted thietane-1,1-dioxides (more than 300 compounds have been studied). The main results of the preclinical evaluation of promising drug candidates with antidepressant activity, 3-methoxythiethane-1,1-dioxide and 3-ethoxythiethane-1,1-dioxide, are presented. Both 3-substituted thietane-1,1-dioxides are char...
Pharmaceutical Chemistry Journal
In continuation of the search for immunotropic compounds among 1-(thietan-3-yl)benzimidazole deri... more In continuation of the search for immunotropic compounds among 1-(thietan-3-yl)benzimidazole derivatives [1], we have synthesized a series of new salts and hydrazides of (benzimidazolyl-2-thio)acetic acids containing thietane cycles. Reactions of 2-[1-(thietan-3-yl)(Ia) and 2-[1-(1,1-dioxothietan-3-yl)(Ib) benzimidazolyl-2-thio]acetic acids with bases (amino alcohols or sodium hydroxide) led to the corresponding salts IIa – IIh. Using ethyl esters IIIa and IIIb, obtained by reacting acids Ia and Ib with ethanol in the presence of sulfuric acid, we synthesized (benzimidazolyl-2-thio)acetic acid hydrazides IVa and IVb, respectively. For biological tests, hydrazides IVa and IVb were converted into dihydrochlorides Va and Vb, respectively.
Pharmaceutical Chemistry Journal
![Research paper thumbnail of ChemInform Abstract: New Synthesis of 6,7-Dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones](https://attachments.academia-assets.com/104604212/thumbnails/1.jpg)
](Russian Journal of Organic Chemistry, 2009
Several methods of synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones have been... more Several methods of synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones have been reported, e.g., from 8-brom-7-(2-haloethyl)-3,7-dihydro1H-purine-2,6-diones and sodium sulfide [1], by reaction of 8-halo-7-(thiiran-2-ylmethyl)-3,7-dihydro-1Hpurin-2,6-diones with nucleophilic reagents [2], etc. We now propose a new one-step procedure for the preparation of 6,7-dihydro[1,3]thiazolo[2,3-f]purin2,4(1H,3H)-dione derivatives via reaction of 8-halo3,7-dihydro-1H-purine-2,6-diones with thiiranes. The reactions were carried out in DMF with 8-halo-3,7-dihydro-1H-purine-2,6-diones Ia–Ic as free bases (in the presence of a base) or potassium salts and an equimolar amount of thiirane IIa–IIc. 6,7-Dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones IIIa–IIIc were thus obtained in 59–68% yield.
![Research paper thumbnail of New synthesis of 5,6-dihydrothiazolo[3,2-b][1,2,4]triazoles](https://attachments.academia-assets.com/104604211/thumbnails/1.jpg)
](Russian Journal of Organic Chemistry, 2009
triazole system may be constructed in several ways: (1) by reaction of 1,2,4-triazole-3(5)-thiols... more triazole system may be constructed in several ways: (1) by reaction of 1,2,4-triazole-3(5)-thiols with 1,2-dibromoethane [1, 2], (2) by cyclization of 3-allylsulfanyl-1,2,4-triazoles by the action of iodine [3], and (3) by reaction of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4triazole with nucleophiles [4]. In the first two methods, isomeric 5,6-dihydrothiazolo[2,3-c][1,2,4]triazoles are formed as by-products [1-3].
Russian Journal of Organic Chemistry, 2009
A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It ... more A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.
Russian Journal of Organic Chemistry, 2011
ABSTRACT By the reaction of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4-triazole with aliphatic and ... more ABSTRACT By the reaction of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4-triazole with aliphatic and aromatic amines 5-aminomethyl-substituted 2-bromo-5,6-dihydrothiazolo[3,2-b]-1,2,4-triazoles were obtained.
Russian Journal of Organic Chemistry, 2009
Russian Journal of Organic Chemistry, 2010
ABSTRACT Reactions of 3-mono- and 3,5-disubstituted 1,2,4-triazoles with a “model” thiirane, 8-br... more ABSTRACT Reactions of 3-mono- and 3,5-disubstituted 1,2,4-triazoles with a “model” thiirane, 8-bromo-1,3-dimethyl-7-(thiiran-2-ylmethyl)-3,7-dihydro-1H-purine-2,6-diones proceed at the positions N1 and N2 of the triazole ring and yield 7-(5-R-3-R′-1,2,4-triazol-1-yl)methyl- and/or 7-(5-R′-3-R-1,2,4-triazol-1-yl)methyl-1,3-dimethyl-6,7-dihydro[1,3]thiazolo[2,3-f]-purine-2,4-(1H,3H)-diones. 3-Methylsulfonyl-1,2,4-triazole reacted regiospecifically at the position N1 forming 1,3-dimethyl-7-[(3-methyl-sulfonyl-1,2,4-triazole-1-yl)-methyl]-6,7-dihydro[1,3]thiazolo-[2,3-f]purine-2,4(1H,3H)-dione.
Russian Journal of Organic Chemistry, 2009
Russian Journal of Organic Chemistry, 2005
Russian Journal of Organic Chemistry, 2008
A new reagent, 3,5-dibromo-1-(1,1-dioxothietanyl-3)-1,2,4-triazole, was introduced for the synthe... more A new reagent, 3,5-dibromo-1-(1,1-dioxothietanyl-3)-1,2,4-triazole, was introduced for the synthesis of 3-substituted thietane 1,1-dioxides that were treated with sodium alcoholates and phenolates to prepare 3-alkoxyand 3-aryloxythietane 1,1-dioxides.
Russian Journal of Organic Chemistry, 2013
Pharmaceutical Chemistry Journal, 2008
Reactions of 3,5-dibromo-1,2,4-triazoles containing thietane or thietane-1,1-dioxide with thiogly... more Reactions of 3,5-dibromo-1,2,4-triazoles containing thietane or thietane-1,1-dioxide with thioglycolic acid yielded 2-[1-(thietanyl-3)-or 2-[1-(1,1-dioxothietanyl-3)-3-bromo-1,2,4-triazolyl-5-thio]acetic acids. Their salts have also been synthesized via reactions with amines and alkalis. Evaluation of the rheological properties showed that some of the synthesized compounds exhibited antiaggregant activity with respect to erythrocytes that was comparable with the effect of pentoxifylline.
HETEROCYCLES, 1990
Treatment of methyl styrylsulfonylacetate with arenediazonium chlorides gave methyl styrylsulfony... more Treatment of methyl styrylsulfonylacetate with arenediazonium chlorides gave methyl styrylsulfonylglyoxylate arenehydrazones, which were cyclized on treatment with bases to 4-aryl-5-phenyl-5,6-dihydro-1,3,4-thiadiazine 1,1-dioxides, a hitherto unknown class of heterocycles
The reactions of the 2-chlorine substituted thietanylbenzimidazols with hydrazine-hydrate have be... more The reactions of the 2-chlorine substituted thietanylbenzimidazols with hydrazine-hydrate have been investigated. The procedures for synthesis of the 2-ilidenhydrazing of tietanylbenzimidazol and also the procedure for synthesis of the ilidenhydrazides of 2-(benzimidazolyl-2-thio) acetic acids containing the tietan cycle have been developed. The early-unknown salts of the 2-(benzimidazolyl-2-thio) acetic acids containing the tientan cycle have been created. The new tietanylbenzimidazol derivatives displaying the immunodepressive, antioxidant, antiaggression and antimicrobic activities have been synthesized. The developed synthesis procedures and discovered structure - activity regularities are used on the departments of pharmaceutic chemistry and microbiology of the Bashkir State Medical University and at the Institute of Organic Chemistry (Ufa Scientific Centre of Russian Academy of Sciences)Available from VNTIC / VNTIC - Scientific & Technical Information Centre of RussiaSIGLERURu...
Russian Journal of Organic Chemistry, 2014
Kazan medical journal
The article presents the results of systematic studies on the search for new biologically active ... more The article presents the results of systematic studies on the search for new biologically active molecules with antidepressant activity in the series of thietane-containing heterocyclic compounds and 3-substituted thietane dioxides. The used strategy for the search for antidepressant substances, based on in vivo pharmacological screening in combination with in silico methods of mathematical modeling and toxico-pharmacokinetic evaluation, is described. Studies of the biological activity of thietane-containing reaction products of azoles with thiiranes have been carried out in the series of thietanylimidazoles, titanixanthines, thietanyltriazoles, thietanyltriazolones, and 3-substituted thietane-1,1-dioxides (more than 300 compounds have been studied). The main results of the preclinical evaluation of promising drug candidates with antidepressant activity, 3-methoxythiethane-1,1-dioxide and 3-ethoxythiethane-1,1-dioxide, are presented. Both 3-substituted thietane-1,1-dioxides are char...
Pharmaceutical Chemistry Journal
In continuation of the search for immunotropic compounds among 1-(thietan-3-yl)benzimidazole deri... more In continuation of the search for immunotropic compounds among 1-(thietan-3-yl)benzimidazole derivatives [1], we have synthesized a series of new salts and hydrazides of (benzimidazolyl-2-thio)acetic acids containing thietane cycles. Reactions of 2-[1-(thietan-3-yl)(Ia) and 2-[1-(1,1-dioxothietan-3-yl)(Ib) benzimidazolyl-2-thio]acetic acids with bases (amino alcohols or sodium hydroxide) led to the corresponding salts IIa – IIh. Using ethyl esters IIIa and IIIb, obtained by reacting acids Ia and Ib with ethanol in the presence of sulfuric acid, we synthesized (benzimidazolyl-2-thio)acetic acid hydrazides IVa and IVb, respectively. For biological tests, hydrazides IVa and IVb were converted into dihydrochlorides Va and Vb, respectively.
Pharmaceutical Chemistry Journal
Russian Journal of Organic Chemistry, 2009
Several methods of synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones have been... more Several methods of synthesis of 6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones have been reported, e.g., from 8-brom-7-(2-haloethyl)-3,7-dihydro1H-purine-2,6-diones and sodium sulfide [1], by reaction of 8-halo-7-(thiiran-2-ylmethyl)-3,7-dihydro-1Hpurin-2,6-diones with nucleophilic reagents [2], etc. We now propose a new one-step procedure for the preparation of 6,7-dihydro[1,3]thiazolo[2,3-f]purin2,4(1H,3H)-dione derivatives via reaction of 8-halo3,7-dihydro-1H-purine-2,6-diones with thiiranes. The reactions were carried out in DMF with 8-halo-3,7-dihydro-1H-purine-2,6-diones Ia–Ic as free bases (in the presence of a base) or potassium salts and an equimolar amount of thiirane IIa–IIc. 6,7-Dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-diones IIIa–IIIc were thus obtained in 59–68% yield.
Russian Journal of Organic Chemistry, 2009
triazole system may be constructed in several ways: (1) by reaction of 1,2,4-triazole-3(5)-thiols... more triazole system may be constructed in several ways: (1) by reaction of 1,2,4-triazole-3(5)-thiols with 1,2-dibromoethane [1, 2], (2) by cyclization of 3-allylsulfanyl-1,2,4-triazoles by the action of iodine [3], and (3) by reaction of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4triazole with nucleophiles [4]. In the first two methods, isomeric 5,6-dihydrothiazolo[2,3-c][1,2,4]triazoles are formed as by-products [1-3].
Russian Journal of Organic Chemistry, 2009
A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It ... more A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.
Russian Journal of Organic Chemistry, 2011
ABSTRACT By the reaction of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4-triazole with aliphatic and ... more ABSTRACT By the reaction of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4-triazole with aliphatic and aromatic amines 5-aminomethyl-substituted 2-bromo-5,6-dihydrothiazolo[3,2-b]-1,2,4-triazoles were obtained.
Russian Journal of Organic Chemistry, 2009
Russian Journal of Organic Chemistry, 2010
ABSTRACT Reactions of 3-mono- and 3,5-disubstituted 1,2,4-triazoles with a “model” thiirane, 8-br... more ABSTRACT Reactions of 3-mono- and 3,5-disubstituted 1,2,4-triazoles with a “model” thiirane, 8-bromo-1,3-dimethyl-7-(thiiran-2-ylmethyl)-3,7-dihydro-1H-purine-2,6-diones proceed at the positions N1 and N2 of the triazole ring and yield 7-(5-R-3-R′-1,2,4-triazol-1-yl)methyl- and/or 7-(5-R′-3-R-1,2,4-triazol-1-yl)methyl-1,3-dimethyl-6,7-dihydro[1,3]thiazolo[2,3-f]-purine-2,4-(1H,3H)-diones. 3-Methylsulfonyl-1,2,4-triazole reacted regiospecifically at the position N1 forming 1,3-dimethyl-7-[(3-methyl-sulfonyl-1,2,4-triazole-1-yl)-methyl]-6,7-dihydro[1,3]thiazolo-[2,3-f]purine-2,4(1H,3H)-dione.
Russian Journal of Organic Chemistry, 2009
Russian Journal of Organic Chemistry, 2005
Russian Journal of Organic Chemistry, 2008
A new reagent, 3,5-dibromo-1-(1,1-dioxothietanyl-3)-1,2,4-triazole, was introduced for the synthe... more A new reagent, 3,5-dibromo-1-(1,1-dioxothietanyl-3)-1,2,4-triazole, was introduced for the synthesis of 3-substituted thietane 1,1-dioxides that were treated with sodium alcoholates and phenolates to prepare 3-alkoxyand 3-aryloxythietane 1,1-dioxides.
Russian Journal of Organic Chemistry, 2013
Pharmaceutical Chemistry Journal, 2008
Reactions of 3,5-dibromo-1,2,4-triazoles containing thietane or thietane-1,1-dioxide with thiogly... more Reactions of 3,5-dibromo-1,2,4-triazoles containing thietane or thietane-1,1-dioxide with thioglycolic acid yielded 2-[1-(thietanyl-3)-or 2-[1-(1,1-dioxothietanyl-3)-3-bromo-1,2,4-triazolyl-5-thio]acetic acids. Their salts have also been synthesized via reactions with amines and alkalis. Evaluation of the rheological properties showed that some of the synthesized compounds exhibited antiaggregant activity with respect to erythrocytes that was comparable with the effect of pentoxifylline.