O. V. Salomatina, S. A. Borisov, M. V. Khvostov, N. I. Komarova, O. A. Luzina, N. F. Salakhutdinov
{"title":"Synthesis and hypoglycemic properties of new derivatives of 3,12-dioxo-5β-cholan-24-oic acid","authors":"O. V. Salomatina, S. A. Borisov, M. V. Khvostov, N. I. Komarova, O. A. Luzina, N. F. Salakhutdinov","doi":"10.1007/s11172-024-4479-0","DOIUrl":"10.1007/s11172-024-4479-0","url":null,"abstract":"<div><p>A library of 1,2,4- and 1,3,4-oxadiazole derivatives of 3,12-dioxo-5β-cholan-24-oic acid containing various substituents at the oxadiazole rings was synthesized from the available animal metabolite of deoxycholic acid <i>via</i> several synthetic approaches. The acquired results of screening of the hypoglycemic activity on the model of alloxan-induced diabetes mellitus in mice revealed for the synthesized compounds that the product containing the 24-nor-3,12-dioxo-5β-cholan and <i>o</i>-pyridine moieties are linked <i>via</i> the 1,3,4-oxadiazole linker on the 8th day reduce the glucose level almost to that in the intact animals. The delayed effect of this compound is presumably related to the influence on the work of genes involved in carbohydrate and lipid metabolisms.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3684 - 3698"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446440","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Levoglucosan as a probe for the study of DMSO—water mixtures using polarimetry","authors":"A. V. Orlova, L. O. Kononov","doi":"10.1007/s11172-024-4491-4","DOIUrl":"10.1007/s11172-024-4491-4","url":null,"abstract":"","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3803 - 3805"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446464","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. A. Obrezkova, A. A. Selifonova, V. K. Revenko, A. M. Muzafarov
{"title":"Erratum to: Searching for the synthetic methods towards siloxane molecular brushes","authors":"M. A. Obrezkova, A. A. Selifonova, V. K. Revenko, A. M. Muzafarov","doi":"10.1007/s11172-024-4492-3","DOIUrl":"10.1007/s11172-024-4492-3","url":null,"abstract":"","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3806 - 3806"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446467","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. V. Pestova, E. S. Izmest’ev, D. V. Petukhov, S. A. Rubtsova
{"title":"Synthesis of 2-oxazolines proceeding from dehydroabietic and 12,14-dinitrodehydroabietic acids","authors":"S. V. Pestova, E. S. Izmest’ev, D. V. Petukhov, S. A. Rubtsova","doi":"10.1007/s11172-024-4481-6","DOIUrl":"10.1007/s11172-024-4481-6","url":null,"abstract":"<div><p>The first three-step synthesis of 2-oxazolines was accomplished using dehydroabietic and 12,14-dinitrodehydroabietic acids. It was shown that the intermediate secondary amides containing fragments of ethanolamine, valinol, tryptophanol, phenylalaninol, and methyl <span>l</span>-serinate can be directly converted into 2-oxazolines by the reaction with toluene-sulfonyl chloride (TsCl) in pyridine or with SOCl<sub>2</sub> in chloroform with subsequent treatment with saturated aqueous NaHCO<sub>3</sub>. The reaction of dehydroabietic acid amide containing a monoethanolamine fragment with TsCl in pyridine was found to give the corresponding chloride in 60% yield instead of 2-oxazoline.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3711 - 3721"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446506","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. A. Popova, I. Yu. Chukicheva, Yu. R. Aleksandrova, M. E. Neganova
{"title":"New coumestans: synthesis, cytotoxic and antioxidant activity","authors":"S. A. Popova, I. Yu. Chukicheva, Yu. R. Aleksandrova, M. E. Neganova","doi":"10.1007/s11172-024-4485-2","DOIUrl":"10.1007/s11172-024-4485-2","url":null,"abstract":"<div><p>New 4-hydroxycoumarins and coumestans with <i>tert</i>-butyl and isobornyl substituents were synthesized. The cytotoxic profile and the antioxidant status of the synthesized compounds were assessed using <i>in vitro</i> models. The promise of the coumestans studied as potential antitumor agents is demonstrated. A possible mechanism of the action of the title compounds is associated with the antioxidant activity expressed in the ability to inhibit the process of lipid peroxidation and with the direct antiradical activity in the ORAC and DPPH assays.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3756 - 3767"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446628","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. V. Mal’shakova, Ya. I. Pylina, L. L. Frolova, A. V. Kutchin, D. V. Belykh
{"title":"Synthesis of hydrophilic chlorophyll derivatives containing terpene and galactose fragments and evaluation of the terpene fragment effect on the photocytotoxicity of target compounds","authors":"M. V. Mal’shakova, Ya. I. Pylina, L. L. Frolova, A. V. Kutchin, D. V. Belykh","doi":"10.1007/s11172-024-4487-0","DOIUrl":"10.1007/s11172-024-4487-0","url":null,"abstract":"<div><p>A series of hydrophilic derivatives of chlorophyll <i>a</i> containing a digalactose fragment and fragments of mono-, di-, and triterpenoids attached to the porphyrin macrocycle through the amide bond were synthesized. The dark and photocytotoxicity of new terpene-containing chlorin-galactose conjugates were assessed in comparison with the chlorin-galactose derivative without the terpene substituent. It was found that the incorporation of the diterpenoid isosteviol increased the photoinduced cytotoxicity against the HeLa cells at a concentration of the target compound of 1 µmol L<sup>−1</sup>. A significant decrease in the survival of the HeLa, A549, and HT-29 cells occurred under the photoinduced exposure to all the studied compounds at a concentration of 10 µmol L<sup>−1</sup>.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3775 - 3784"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446459","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, N. E. Nifantiev
{"title":"Polyphenolic components of extracts from the knot wood of plum “Renklod sinii” (Renclode blue)","authors":"D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, N. E. Nifantiev","doi":"10.1007/s11172-024-4486-1","DOIUrl":"10.1007/s11172-024-4486-1","url":null,"abstract":"<div><p>Catechin, proanthocyanidin B-2, epiafzelechin-(4β→8)-epicatechin, dihydroquercetin, and eriodictyol were isolated <i>via</i> the extraction from the knot wood of plum <i>Renclode blue</i> (<i>Prunus domestica “Renklod sinii”</i>) and subsequent HPLC. Structures of these compounds were confirmed using 2D NMR spectroscopy and mass spectrometry.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3768 - 3774"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446465","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
P. L. Kuznetsova, V. E. Shambalova, A. S. Aldoshin, K. A. Lyssenko, V. G. Nenajdenko
{"title":"Preparation of fluorinated 5,5′-dialkylsubstituted dipyrromethanes","authors":"P. L. Kuznetsova, V. E. Shambalova, A. S. Aldoshin, K. A. Lyssenko, V. G. Nenajdenko","doi":"10.1007/s11172-024-4471-8","DOIUrl":"10.1007/s11172-024-4471-8","url":null,"abstract":"<div><p>A synthetic approach to novel fluorinated 5,5′-dialkyl-substituted dipyrromethanes based on acid-catalyzed condensation of the corresponding pyrroles and ketones was developed. High efficiency of this transformation for a wide range of pyrroles and ketones was demonstrated using trifluoromethanesulfonic acid as a catalyst. A series of novel fluorinated dipyrromethanes was obtained in high yields.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3601 - 3611"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446388","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. E. Ivanova, M. V. Goryaeva, Ya. V. Burgart, P. A. Slepukhin, V. I. Saloutin
{"title":"Synthesis and competitive functionalization of ethyl 4-aryl-2-oxo- and ethyl 4-aryl-2-thioxo-6-(trifluoromethyl)tetrahydropyrimidine-5-carboxylates","authors":"A. E. Ivanova, M. V. Goryaeva, Ya. V. Burgart, P. A. Slepukhin, V. I. Saloutin","doi":"10.1007/s11172-024-4473-6","DOIUrl":"10.1007/s11172-024-4473-6","url":null,"abstract":"<div><p>Efficient conditions were found for the dehydration of ethyl 6-aryl-4-hydroxy-2-oxo- and ethyl 6-aryl-4-hydroxy-2-thioxo-4-(trifluoromethyl)hexahydropyrimidine-5-carboxylates that formed in the Biginelli reaction from trifluoroacetoacetic ester, aldehyde, and (thio)urea. In the presence of thionyl chloride and pyridine, the dehydration affords tetrahydropyrimidines. Under these conditions, 4-CF<sub>3</sub>-2-thioxohexahydropyrimidine bearing an <i>ortho</i>-hydroxy group in the aryl substituent undergo cyclization to form ethyl 4-thioxotetrahydromethanobenzo[<i>g</i>][1,3,5]oxadiazocine-11-carboxylate. In the methylation and alkoxymethylation reactions, ethyl 4-aryl-2-oxo(thioxo)-6-(trifluoromethyl)tetrahydropyrimidine-5-carboxylates show an ambident nucleophilic character, reacting at the N(1), N(3), O, or S centers. Methyl-<i>N</i>(1)-tetrahydropyrimidines were obtained as the major methylation products; while the alkoxymethylation with paraformaldehyde and various alcohols afforded <i>N</i>(3)-substituted derivatives.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3624 - 3637"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446504","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. S. Borisova, D. S. Kuliukhina, A. S. Malysheva, A. V. Murashkina, A. D. Averin, V. V. Vergun, V. I. Isaeva, E. N. Savelyev, I. A. Novakov, I. P. Beletskaya
{"title":"Copper-based metal-organic frameworks as catalysts for the amination of aryl iodides","authors":"A. S. Borisova, D. S. Kuliukhina, A. S. Malysheva, A. V. Murashkina, A. D. Averin, V. V. Vergun, V. I. Isaeva, E. N. Savelyev, I. A. Novakov, I. P. Beletskaya","doi":"10.1007/s11172-024-4467-4","DOIUrl":"10.1007/s11172-024-4467-4","url":null,"abstract":"<div><p>Copper-based metal-organic frameworks (Cu-MOFs) were successfully used for the amination of aryl iodides for the first time. The conditions were selected using four different Cu-MOFs in a model reaction of <i>n</i>-octylamine with iodobenzene. Efficient reaction requires the use of <i>O,O</i>′-bidentate ligands (2-acetylcyclohexanone, 2-isobutyrylcyclo-hexanone, <i>rac</i>-1,1′-bi(2-naphthol), or <i>rac</i>-BINOL), and, in the best cases, the yields of <i>N</i>-octylaniline can exceed 80%. The nature of MOF does not produce a strong effect on the reaction outcome. The amination of iodobenzene derivatives containing electron-donating and electron-withdrawing substituents in the <i>para</i>- and <i>meta</i>-positions was investigated. The study also demonstrated the possibility of successful <i>N</i>-arylation of adamantane-containing amines with iodobenzene and its derivatives in the presence of MOFs and <i>rac</i>-BINOL or 2-isobutyrylcyclohexanone ligands. The yields of the products were found to depend on the steric hindrances at the nitrogen atom, with the best yields (87–88%) being obtained in the <i>N,N</i>′-diarylation of adamantanediamines. Using the reaction of <i>n</i>-octylamine with iodobenzene, the possibility of catalyst reuse for up to 10 cycles was demonstrated.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3567 - 3577"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446441","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}