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Synthesis and Anticancer Activity of Ergosterol Peroxide 3-Carbamate Pyrazole Side-Chain Derivatives
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120260
S. Q. Deng, T. C. Xu, Z. G. Zhang, C. H. Xie, X. H. Du, H. L. Li, M. Bu
{"title":"Synthesis and Anticancer Activity of Ergosterol Peroxide 3-Carbamate Pyrazole Side-Chain Derivatives","authors":"S. Q. Deng,&nbsp;T. C. Xu,&nbsp;Z. G. Zhang,&nbsp;C. H. Xie,&nbsp;X. H. Du,&nbsp;H. L. Li,&nbsp;M. Bu","doi":"10.1134/S1070363224120260","DOIUrl":"10.1134/S1070363224120260","url":null,"abstract":"<p>Fifteen ergosterol peroxide-3-carbamate pyrazole derivatives were successfully synthesized and evaluated their cytotoxicity <i>in vitro</i> against human lung cancer A549 cell line, human hepatocellular carcinoma HepG2 cell line, human breast cancer MCF-7 cell line and human hepatic LO2 cell lines. Among them, ergosterol peroxide-3-piperazine-1-ethyl-5-pyrazole showed a strong cytotoxicity with an IC<sub>50</sub> of 3.01 μM against HepG2 cells, which was 6-fold higher than that of ergosterol peroxide. Further study of the mechanisms suggests that ergosterol peroxide-3-piperazine-1-ethyl-5-pyrazole had a total apoptosis rate of 61.04% at a concentration of 6 μM and promotes reactive oxygen species (ROS) production in a dose-dependent manner in HepG2 cells. These findings suggest that the apoptosis and the generation of ROS may be two key indicators of oxidative stress induced by ergosterol peroxide-3-piperazine-1-ethyl-5-pyrazole. Based on these results, we further explored the molecular docking between ergosterol peroxide-3-piperazine-1-ethyl-5-pyrazole and heat shock protein 90 (HSP90), discovering a strong binding affinity between them. This suggests that ergosterol peroxide-3-piperazine-1-ethyl-5-pyrazole may exert its antitumor effects through oxidative stress.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3348 - 3362"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109602","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
Ionic Ni Metal Bis-Dithiolene Complexes: Synthesis, Electronic Properties and Photo-Thermal Stability
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120314
Y. Niu, X. Duan, A. Han
{"title":"Ionic Ni Metal Bis-Dithiolene Complexes: Synthesis, Electronic Properties and Photo-Thermal Stability","authors":"Y. Niu,&nbsp;X. Duan,&nbsp;A. Han","doi":"10.1134/S1070363224120314","DOIUrl":"10.1134/S1070363224120314","url":null,"abstract":"<p>Several anionic nickel(bis-dithiolene) complexes were conveniently synthesized by utilizing the neutral metal dithiolene complexes as a starting material at the presence of triethylamine, and these structures were confirmed by the high-resolution mass (HRMS), UV-Vis-NIR, XPS and IR spectroscopy, their physical properties were investigated. The results indicate that the new approach is suitable to prepare the ionic nickel(bis-dithiolene) complexes at a great quantity.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3393 - 3400"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109747","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, Modification, and In Vitro Antimicrobial Activity of 3,4-Dihydro-4,6-diaryl-2-pyrimidinethiones
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120077
A. S. Skrylkova, D. M. Egorov, A. S. Krylov, E. N. Chernova, I. L. Kuzikova, Z. A. Zhakovskaya
{"title":"Synthesis, Modification, and In Vitro Antimicrobial Activity of 3,4-Dihydro-4,6-diaryl-2-pyrimidinethiones","authors":"A. S. Skrylkova,&nbsp;D. M. Egorov,&nbsp;A. S. Krylov,&nbsp;E. N. Chernova,&nbsp;I. L. Kuzikova,&nbsp;Z. A. Zhakovskaya","doi":"10.1134/S1070363224120077","DOIUrl":"10.1134/S1070363224120077","url":null,"abstract":"<p>A series of 3,4-dihydro-4,6-diaryl-2-pyrimidinethiones was obtained using a three-component reaction and their modifiaction with dimethyl chloroethynylphosphonate was performed. It was shown that the phosphonylation reaction occurs under mild conditions and chemo- and regioselectively leads to bicyclic products, namely dimethyl 5,7-diaryl-5<i>H</i>-thiazolo[3,2-<i>a</i>]pyrimidine-3-phosphonates. Antimicrobial activity of the synthesized compounds against <i>Staphylococcus aureus</i> and <i>Pseudomonas aeruginosa</i> bacteria and yeast-like fungi <i>Candida utilis</i> was studied.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3181 - 3189"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070363224120077.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109431","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Bulky 4-Amino-1,3-diarylimidazolium Salts as NHC-Ligand Precursors and Derived M/NHC Complexes (M = Cu, Pd)
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S107036322412017X
M. A. Shevchenko, A. Yu. Malakhov, V. M. Chernyshev
{"title":"Synthesis of Bulky 4-Amino-1,3-diarylimidazolium Salts as NHC-Ligand Precursors and Derived M/NHC Complexes (M = Cu, Pd)","authors":"M. A. Shevchenko,&nbsp;A. Yu. Malakhov,&nbsp;V. M. Chernyshev","doi":"10.1134/S107036322412017X","DOIUrl":"10.1134/S107036322412017X","url":null,"abstract":"<p>An approach was developed for the synthesis of novel 1,3-bis(4-R-2,6-dibenzhydrylphenyl)-4aminoimidazolium chlorides, precursors of amino-functionalized sterically bulky NHC ligands, starting from N-aryl formamides via reaction with POCl<sub>3</sub> with subsequent amination of the <i>in situ</i> formed imidoyl chloride with arylamine and condensation of the thus formed formamidine with chloroacetonitrile. The applicability of the aminoimidazolium salts obtained for further functionalization of the NH<sub>2</sub> group and selective metalation of the imidazole C<sup>2</sup>–H bond to give Cu/NHC and Pd/NHC complexes was demonstrated.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3263 - 3276"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109595","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
6-Nitroazolo[1,5-a]pyrimidines and 6-Nitroazolo[5,1-c][1,2,4]triazines in the Nucleophilic Sulfation Reaction
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120119
Е. B. Gorbunov, P. А. Slepukhin, R. I. Ishmetova, N. А. Gerasimova, N. P. Evstigneeva, G. L. Rusinov
{"title":"6-Nitroazolo[1,5-a]pyrimidines and 6-Nitroazolo[5,1-c][1,2,4]triazines in the Nucleophilic Sulfation Reaction","authors":"Е. B. Gorbunov,&nbsp;P. А. Slepukhin,&nbsp;R. I. Ishmetova,&nbsp;N. А. Gerasimova,&nbsp;N. P. Evstigneeva,&nbsp;G. L. Rusinov","doi":"10.1134/S1070363224120119","DOIUrl":"10.1134/S1070363224120119","url":null,"abstract":"<p>A method has been developed for the introduction of a sulfo group into molecules of 6-nitro derivatives of azoloanneled [1,5-<i>a</i>]pyrimidines and [5,1-<i>c</i>][1,2,4]triazines via a nucleophilic addition reaction (A<sub>N</sub>). The antimicrobial activity of some synthesized compounds was evaluated with respect to the control strain of <i>Neisseria gonorrhoeae</i> ATCC 49226/NCTC 12700 and museum strains of dermatophyte fungi and yeast-like fungi.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3217 - 3222"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109495","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
The Capacity of the R[OE(C6F5)2]2 (E = B, Al; R = C2H4, p-C6H4, m-C6H4) Complexes with Pyrazine and 3,3′-Bipyridine Towards Activation of Hydrogen Molecules
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S107036322412020X
A. S. Lisovenko, I. V. Kazakov
{"title":"The Capacity of the R[OE(C6F5)2]2 (E = B, Al; R = C2H4, p-C6H4, m-C6H4) Complexes with Pyrazine and 3,3′-Bipyridine Towards Activation of Hydrogen Molecules","authors":"A. S. Lisovenko,&nbsp;I. V. Kazakov","doi":"10.1134/S107036322412020X","DOIUrl":"10.1134/S107036322412020X","url":null,"abstract":"<p>Thermodynamic parameters of the process of dissociation of the donor-acceptor complexes of bidentate Lewis acids R[OE(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>]<sub>2</sub> (E = B, Al; R = C<sub>2</sub>H<sub>4</sub>, <i>p</i>-C<sub>6</sub>H<sub>4</sub>, <i>m</i>-C<sub>6</sub>H<sub>4</sub>) with pyrazine (pyz) and 3,3′-bipyridine (bipy) have been determined by means of quantum-chemical simulation (M06-2X/def2-TZVP). A combination of the bidentate Lewis acid and the bidentate Lewis base may result in the formation of one or two donor-acceptor bonds. The formation of the hos-guest type complexes can be observed in the case of the formation of two donor-acceptor bonds. The non-optimal size of the donor and the acceptor molecules has led to the strain in the formed cyclic compound, which can be reflected in the possibility of the heterolytic rupture of hydrogen molecule (into the Н<sup>+</sup> and Н<sup>–</sup> ions), analogous to the Frustrated Lewis Pairs (FLP). The performed quantum-chemical simulations of the energy and thermodynamic parameters of the processes of activation of molecular hydrogen with the R[OE(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>]<sub>2</sub>·LB (E = B, Al; LB = pyz, bipy; R = C<sub>2</sub>H<sub>4</sub>, <i>p</i>-C<sub>6</sub>H<sub>4</sub>, <i>m</i>-C<sub>6</sub>H<sub>4</sub>) complexes in the gas phase have evidenced the prospects of further optimization of the size and acid-base properties of the bidentate donor and acceptor.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3296 - 3302"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109600","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
Vapor-Phase Oxidation of Benzyl Alcohol into Benzaldehyde Using Biphasic Ce–Mn Catalyst in Presence of Air
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120338
P. V. Reddy, G. Saidulu, G. R. Kumar, P. Bhadraiah, D. Mallesh, S. Swapna
{"title":"Vapor-Phase Oxidation of Benzyl Alcohol into Benzaldehyde Using Biphasic Ce–Mn Catalyst in Presence of Air","authors":"P. V. Reddy,&nbsp;G. Saidulu,&nbsp;G. R. Kumar,&nbsp;P. Bhadraiah,&nbsp;D. Mallesh,&nbsp;S. Swapna","doi":"10.1134/S1070363224120338","DOIUrl":"10.1134/S1070363224120338","url":null,"abstract":"<p>Here, we present the efficient synthesis of benzaldehyde (BnZ) by reacting benzyl alcohol with air and employing CeO<sub>2</sub>–MnO<sub>2</sub> (Ce–Mn) mixed oxide. The addition of MnO<sub>2</sub> (Mn) to CeO<sub>2</sub>(Ce) increased the reducibility, support–support interaction, and oxygen vacancy. The development of oxygen vacancies in the ceria lattice following Mn addition can be used to explain that altering the Mn:Ce ratio refines the oxide’s reducibility. The physicochemical characteristics of the synthesized materials were examined using FT-IR, Raman spectroscopy, powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS), and BET surface area analysis. Furthermore, it exhibits superior catalytic activity in the presence of air during the selective oxidation of benzyl alcohol to benzaldehyde in vapor phase reactions, and it keeps its high stability for five successive cycles.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3413 - 3423"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109649","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 5,6-Dialkyl-4-aryl-2-aminopyridine-3-carbonitriles and In Vitro Study of Their Antimicrobial Activity
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120065
D. S. Bespalov, D. M. Egorov, A. S. Krylov, E. N. Chernova, I. L. Kuzikova, Z. A. Zhakovskaya
{"title":"Synthesis of 5,6-Dialkyl-4-aryl-2-aminopyridine-3-carbonitriles and In Vitro Study of Their Antimicrobial Activity","authors":"D. S. Bespalov,&nbsp;D. M. Egorov,&nbsp;A. S. Krylov,&nbsp;E. N. Chernova,&nbsp;I. L. Kuzikova,&nbsp;Z. A. Zhakovskaya","doi":"10.1134/S1070363224120065","DOIUrl":"10.1134/S1070363224120065","url":null,"abstract":"<p>A three-component reaction for the synthesis of highly functionalized pyridine derivatives was studied. The cyclization reaction patterns were investigated, and it was shown that in the case of using methyl ethyl ketone and methyl isobutyl ketone, the methylene group participates in the condensation reaction. The biological activity of the obtained compounds against the <i>Staphylococcus aureus</i> and <i>Pseudomonas aeruginosa</i> bacteria, as well as <i>Candida utilis</i> yeast-like fungi was studied, and compounds with high antibacterial activity were revealed.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3173 - 3180"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109678","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
Bis-Semiquinonate Copper Complexes with 4,4′-Bipyridine. Coordination Sphere Dynamics
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120296
A. V. Cherkasova, G. V. Romanenko, A. V. Cherkasov, V. A. Kuropatov
{"title":"Bis-Semiquinonate Copper Complexes with 4,4′-Bipyridine. Coordination Sphere Dynamics","authors":"A. V. Cherkasova,&nbsp;G. V. Romanenko,&nbsp;A. V. Cherkasov,&nbsp;V. A. Kuropatov","doi":"10.1134/S1070363224120296","DOIUrl":"10.1134/S1070363224120296","url":null,"abstract":"<p>We studied the reactions of sterically hindered bis-semiquinonates of copper(II) with 4,4′-bipyridine. Coordination polymer consisting of metallamacrocyclic binuclear copper(II) cage-like moieties bridged with 4,4′-bipyridine linkers was isolated in the reaction of copper(II) bis-semiquinonate metallamacrocycle with 4,4′-bipyridine. It is important that the initial and final metallamacrocycles in this reaction are different by the disposition of semiquinone units in the coordination surroundings of copper (II) ions. The transformation of one metallamacrocycle into another could only be achieved by a two-fold sequential cleavage of the metal-semiquinone bond.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3378 - 3385"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109746","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 Cytostatic Activity of Substituted Derivatives of Sodium 1-Amino-2-cyano-1,6-dioxo-4-{[3-(ethoxycarbonyl)thiophen-2-yl]amino}hexa-2,4-dien-3-olates
IF 0.9 4区 化学
Russian Journal of General Chemistry Pub Date : 2025-01-27 DOI: 10.1134/S1070363224120028
I. A. Gorbunova, K. A. Mitusova, K. Yu. Parkhoma, Yu. O. Sharavyova, R. R. Makhmudov, O. Yu. Ustinova, E. S. Denislamova, D. A. Shipilovskikh
{"title":"Synthesis and Cytostatic Activity of Substituted Derivatives of Sodium 1-Amino-2-cyano-1,6-dioxo-4-{[3-(ethoxycarbonyl)thiophen-2-yl]amino}hexa-2,4-dien-3-olates","authors":"I. A. Gorbunova,&nbsp;K. A. Mitusova,&nbsp;K. Yu. Parkhoma,&nbsp;Yu. O. Sharavyova,&nbsp;R. R. Makhmudov,&nbsp;O. Yu. Ustinova,&nbsp;E. S. Denislamova,&nbsp;D. A. Shipilovskikh","doi":"10.1134/S1070363224120028","DOIUrl":"10.1134/S1070363224120028","url":null,"abstract":"<p>A series of new substituted derivatives of sodium 1-amino-1,6-dioxo-2-cyano-4-{[3-(ethoxycarbonyl)thiophen-2-yl]amino}hexa-2,4-dien-3-olates was synthesized by the furan ring opening reaction of substituted 3-thienylimino-3<i>H</i>-furan-2-ones under the action of amide of cyanoacetic acid in the presence of sodium carbonate as a base. The cytotoxic effect on 4T1 breast cancer cells was studied and the acute toxicity of the obtained compounds was assessed. It was found that the obtained compounds have pronounced anticancer activity and are practically non-toxic drugs (hazard class IV).</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"94 12","pages":"3140 - 3148"},"PeriodicalIF":0.9,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143109411","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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