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Synthesis of methylated and trifluoromethylated hydroxy thiols based on myrtenal
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4470-9
N. O. Ilchenko, D. V. Sudarikov, R. V. Rumyantcev, S. A. Rubtsova, A. V. Kutchin
{"title":"Synthesis of methylated and trifluoromethylated hydroxy thiols based on myrtenal","authors":"N. O. Ilchenko,&nbsp;D. V. Sudarikov,&nbsp;R. V. Rumyantcev,&nbsp;S. A. Rubtsova,&nbsp;A. V. Kutchin","doi":"10.1007/s11172-024-4470-9","DOIUrl":"10.1007/s11172-024-4470-9","url":null,"abstract":"<div><p>A new method was developed for the stereoselective synthesis of methylated and trifluoromethylated thiols based on (1<i>R</i>)-(–)-myrtenal. The CF<sub>3</sub>-substituted ketone and CH<sub>3</sub>-substituted thioacetate, which are required for the synthesis of the corresponding thiols, were prepared for the first time in 83% and 73% yields, respectively. The yields of CH<sub>3</sub>- and CF<sub>3</sub>-substituted thiols are 70% (<i>de</i> &gt;99%) and 53% (<i>de</i> &gt;99%) after two steps, respectively.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3593 - 3600"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446444","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}
引用次数: 0
Benzyltrimethylammonium tribromide in bromination of some semisynthetic and natural phenols
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4490-5
E. V. Buravlev
{"title":"Benzyltrimethylammonium tribromide in bromination of some semisynthetic and natural phenols","authors":"E. V. Buravlev","doi":"10.1007/s11172-024-4490-5","DOIUrl":"10.1007/s11172-024-4490-5","url":null,"abstract":"<div><p>It was shown that benzyltrimethylammonium tribromide is a convenient reagent for the synthesis of bromo derivatives of 2-isobornylphenols and natural phenolic compounds, <i>viz.</i>, thymol and carvacrol. The use of this reagent allows synthesizing mono- and dihalogenated products bearing the substituents at the <i>ortho</i>- and/or <i>para</i>-positions.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3799 - 3802"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446466","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}
引用次数: 0
Synthesis of the substituted derivatives of sodium 5-aryl-5-oxo-3-[(thiophen-2-yl)amino]penta-1,3-dien-2-olates and evaluation of their antinociceptive activity in vivo
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4477-2
I. A. Gorbunova, K. Yu. Parkhoma, D. A. Kozlov, I. P. Nikonov, E. S. Denislamova, R. R. Makhmudov, D. A. Shipilovskikh
{"title":"Synthesis of the substituted derivatives of sodium 5-aryl-5-oxo-3-[(thiophen-2-yl)amino]penta-1,3-dien-2-olates and evaluation of their antinociceptive activity in vivo","authors":"I. A. Gorbunova,&nbsp;K. Yu. Parkhoma,&nbsp;D. A. Kozlov,&nbsp;I. P. Nikonov,&nbsp;E. S. Denislamova,&nbsp;R. R. Makhmudov,&nbsp;D. A. Shipilovskikh","doi":"10.1007/s11172-024-4477-2","DOIUrl":"10.1007/s11172-024-4477-2","url":null,"abstract":"<div><p>New substituted derivatives of 5-aryl-5-oxo-3-[(thiophen-2yl)amino]penta-1,3-dien-2-olates were synthesized by the reaction of the substituted 3-[(thiophen-2-yl)imino]furan-2(3<i>H</i>)-ones with cyanoacetic acid derivatives in the presence of sodium carbonate. The <i>in vivo</i> experiments revealed that the synthesized sodium salts possess pronounced antinociceptive activity that exceeded the activity of the reference drug (metamizole sodium). Sodium 1-amino-2-cyano-4-{[3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[<i>b</i>]thiophen-2-yl]amino}-6-(4-methoxyphenyl)-1,6-dioxohexa-2,4-dien-3-olate demonstrated the highest activity exceeding that of metamizole sodium by ⩾1.5 times. Acute toxicity of all studied compounds (median lethal dose values (LD<sub>50</sub>)) was greater than 1500 mg kg<sup>−1</sup> being six times higher than the LD<sub>50</sub> value for metamizole sodium.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3669 - 3676"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446438","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}
引用次数: 0
Synthesis of new aryl derivatives of isobornylphenols by the Suzuki reaction
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4469-2
T. A. Kolegova, Ya. A. Gur’eva, I. Yu. Chukicheva, O. A. Zalevskaya, A. V. Kutchin
{"title":"Synthesis of new aryl derivatives of isobornylphenols by the Suzuki reaction","authors":"T. A. Kolegova,&nbsp;Ya. A. Gur’eva,&nbsp;I. Yu. Chukicheva,&nbsp;O. A. Zalevskaya,&nbsp;A. V. Kutchin","doi":"10.1007/s11172-024-4469-2","DOIUrl":"10.1007/s11172-024-4469-2","url":null,"abstract":"<div><p>New aryl derivatives of terpenophenols were obtained by cross-coupling of the corresponding bromo-substituted isobornylphenols with arylboronic acids under the Suzuki reaction conditions. A number of palladium complexes with terpene <i>N</i>-donor ligands were tested as catalysts for the reaction. The most optimal reagents and reaction conditions were established.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3586 - 3592"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446443","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}
引用次数: 0
Molecular design of multitarget neuroprotective agents 6. Synthesis of conjugates of tetrahydro-γ-carbolines and adamantan-1-amines combined via a trimethylene linker
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4478-1
A. Yu. Aksinenko, T. V. Goreva, T. A. Epishina, A. N. Ivanov, S. O. Bachurin
{"title":"Molecular design of multitarget neuroprotective agents 6. Synthesis of conjugates of tetrahydro-γ-carbolines and adamantan-1-amines combined via a trimethylene linker","authors":"A. Yu. Aksinenko,&nbsp;T. V. Goreva,&nbsp;T. A. Epishina,&nbsp;A. N. Ivanov,&nbsp;S. O. Bachurin","doi":"10.1007/s11172-024-4478-1","DOIUrl":"10.1007/s11172-024-4478-1","url":null,"abstract":"<div><p>A method for the synthesis of new conjugates of tetrahydro-γ-carbolines and adamantan-1-amines linked <i>via</i> a trimethylene spacer was developed.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3677 - 3683"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446439","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}
引用次数: 0
Synthesis and antimicrobial activity of alkyl[2-(5-chloro-2-hydroxyphenyl)hex-1-en-1-yl]diphenylphosphonium salts
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4480-7
D. A. Tatarinov, E. A. Mikulenkova, N. V. Terekhova, A. V. Nemtarev, A. P. Lyubina, A. D. Voloshina, A. S. Sapunova, A. B. Dobrynin, I. A. Litvinov, V. F. Mironov
{"title":"Synthesis and antimicrobial activity of alkyl[2-(5-chloro-2-hydroxyphenyl)hex-1-en-1-yl]diphenylphosphonium salts","authors":"D. A. Tatarinov,&nbsp;E. A. Mikulenkova,&nbsp;N. V. Terekhova,&nbsp;A. V. Nemtarev,&nbsp;A. P. Lyubina,&nbsp;A. D. Voloshina,&nbsp;A. S. Sapunova,&nbsp;A. B. Dobrynin,&nbsp;I. A. Litvinov,&nbsp;V. F. Mironov","doi":"10.1007/s11172-024-4480-7","DOIUrl":"10.1007/s11172-024-4480-7","url":null,"abstract":"<div><p>A series of alkyl[2-(5-chloro-2-hydroxyphenyl)hex-1-en-1-yl]diphenylphosphonium salts were synthesized based on the predicted lipophilicity (log<i>P</i>). The synthesized salts exhibited high antimicrobial activity against gram-positive bacterial and fungal strains and high activity against the antibiotic-resistant <i>Staphylococcus aureus</i> (MRSA) strains. The most active compounds showed low cytotoxicity against human erythrocytes and liver cells and exhibited high selectivity indices.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3699 - 3710"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446460","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}
引用次数: 0
Synthesis of a new glycosyl-acceptor derivative of normuramic acid lactam and its use for the preparation of a spacer-armed disaccharide structurally similar to the repeating fragment of the bacterial spore cell wall peptidoglycan
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4482-5
S. S. Pertel, E. S. Kakayan, A. I. Zinin, L. O. Kononov
{"title":"Synthesis of a new glycosyl-acceptor derivative of normuramic acid lactam and its use for the preparation of a spacer-armed disaccharide structurally similar to the repeating fragment of the bacterial spore cell wall peptidoglycan","authors":"S. S. Pertel,&nbsp;E. S. Kakayan,&nbsp;A. I. Zinin,&nbsp;L. O. Kononov","doi":"10.1007/s11172-024-4482-5","DOIUrl":"10.1007/s11172-024-4482-5","url":null,"abstract":"<div><p>A new, highly reactive spacer-armed glycosyl-acceptor derivative of normuramic acid latam was synthesised using an optimized synthetic scheme. The scheme allowed the complete suppression of the side intramolecular <i>N</i>-alkylation reaction occurring during the preparation of this substance using a method based on intramolecular 3-<i>O</i>-alkylation. It was shown that intramolecular <i>N</i>-alkylation in the 3-chloropropylglycoside derivative of normuramic acid lactam led to the formation of an unusual tetracyclic derivative. The reaction of the synthesized reactive glycosyl-acceptor 4-hydroxy derivative with the lowre active 2-methyl-glucopyrano-[2,1-<i>d</i>]-2-oxazoline glycosyl-donor resulted in a spacer-armed disaccharide derivative of normuramic acid lactam structurally similar to the repeating fragment of the bacterial spore cell wall peptidoglycan.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3722 - 3731"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446505","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}
引用次数: 0
Halogenation of cyclic olefins containing spiroconjugated imidazolone moiety
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4474-5
D. E. Shybanov, M. E. Kukushkin, V. A. Tafeenko, Yu. K. Grishin, N. V. Zyk, E. K. Beloglazkina
{"title":"Halogenation of cyclic olefins containing spiroconjugated imidazolone moiety","authors":"D. E. Shybanov,&nbsp;M. E. Kukushkin,&nbsp;V. A. Tafeenko,&nbsp;Yu. K. Grishin,&nbsp;N. V. Zyk,&nbsp;E. K. Beloglazkina","doi":"10.1007/s11172-024-4474-5","DOIUrl":"10.1007/s11172-024-4474-5","url":null,"abstract":"<div><p>The electrophilic halogenation of spirocyclic olefins containing an imidazolone fragment were studied using techniques of dropwise addition of halogen and diffusion mixing with halogen vapor. The bromination reactions providing the formation of <i>trans</i>-1,2-dihalogenation products (when reactions with bridging olefin are carried out in chloroform) or skeletal rearrangements (reactions in acetonitrile or methanol) are most chemo- and stereoselective. Chlorination is nonselective with the formation of mixtures of products, and success of iodination is determined by the choice of the substrate and reaction conditions.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3638 - 3646"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446435","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}
引用次数: 0
Lewis acids in the synthesis of naphthoquinonylbenzo[g]chromenediones, derivatives of mesocentroquinone, a metabolite of the sea urchins Mesocentrotus nudus and Strongylocentrotus intermedius
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4489-y
K. L. Borisova, D. N. Pelageev, V. Ph. Anufriev
{"title":"Lewis acids in the synthesis of naphthoquinonylbenzo[g]chromenediones, derivatives of mesocentroquinone, a metabolite of the sea urchins Mesocentrotus nudus and Strongylocentrotus intermedius","authors":"K. L. Borisova,&nbsp;D. N. Pelageev,&nbsp;V. Ph. Anufriev","doi":"10.1007/s11172-024-4489-y","DOIUrl":"10.1007/s11172-024-4489-y","url":null,"abstract":"<div><p>An approach was developed for the synthesis of naphthoquinonylbenzo[<i>g</i>]chromenedions, derivatives of mesocentroquinone, a metabolite of the sea urchins <i>Mesocentrotus nudus</i> and <i>Strongylocentrotus intermedius</i>. The key stage in the developed approach is the previously undescribed heterodiene condensation of 2-oxo-3-alkylidene- and 3-alkenyl-2-hydroxy-1,4-naphthoquinones formed during dehydrobromination of the corresponding 3-(1-bromoalkyl)-2-hydroxy derivatives in the presence of Lewis acid (SnCl<sub>4</sub>).</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3793 - 3798"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446462","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}
引用次数: 0
First example of the synthesis of 2H-labeled derivatives of the phytoecdysteroid 20-hydroxyecdysone
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2025-02-20 DOI: 10.1007/s11172-024-4488-z
R. G. Savchenko, O. S. Mozgovoy, E. A. Paramonov, L. M. Khalilov, A. I. Samigullina, L. V. Parfenova
{"title":"First example of the synthesis of 2H-labeled derivatives of the phytoecdysteroid 20-hydroxyecdysone","authors":"R. G. Savchenko,&nbsp;O. S. Mozgovoy,&nbsp;E. A. Paramonov,&nbsp;L. M. Khalilov,&nbsp;A. I. Samigullina,&nbsp;L. V. Parfenova","doi":"10.1007/s11172-024-4488-z","DOIUrl":"10.1007/s11172-024-4488-z","url":null,"abstract":"<div><p>Alternative approaches were developed to introduce deuterium atoms into the steroid backbone and the side chain of a short-chain derivative of the phytoecdysteroid 20-hydroxyecdysone, poststerone acetonide, using LiAlD<sub>4</sub> and D<sub>2</sub>O as deuterating agents.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3785 - 3792"},"PeriodicalIF":1.7,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143446463","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}
引用次数: 0
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