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Synthesis and Reactivity of 2-(Thiophen-2-yl)naphtho[2,1-d][1,3]thiazole
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S107042802412011X
A. A. Aleksandrov, V. V. Kutyrev
{"title":"Synthesis and Reactivity of 2-(Thiophen-2-yl)naphtho[2,1-d][1,3]thiazole","authors":"A. A. Aleksandrov,&nbsp;V. V. Kutyrev","doi":"10.1134/S107042802412011X","DOIUrl":"10.1134/S107042802412011X","url":null,"abstract":"<p>The condensation of naphthalen-2-amine with thiophene-2-carbonyl chloride in propan-2-ol gave <i>N</i>-(naphthalen-2-yl)thiophene-2-carboxamide whose treatment with excess P<sub>2</sub>S<sub>5</sub> in anhydrous toluene afforded the corresponding thioamide. Oxidation of the latter with potassium ferricyanide in alkaline medium led to the formation of 2-(thiophen-2-yl)naphtho[2,1-<i>d</i>][1,3]thiazole. The cyclization involving C<sup>1</sup> of the naphthalene ring was substantiated by quantum chemical calculations. The title compound was subjected to electrophilic substitution reactions, including nitration, bromination, formylation, and acylation, in which the electrophile entered exclusively position <i>5</i> of the thiophene ring.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2388 - 2392"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362002","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
Reaction of Substituted Chalcone with Guanidine in the Presence of Hydrogen Peroxide
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S107042802412025X
I. G. Mamedov, V. N. Khrustalev
{"title":"Reaction of Substituted Chalcone with Guanidine in the Presence of Hydrogen Peroxide","authors":"I. G. Mamedov,&nbsp;V. N. Khrustalev","doi":"10.1134/S107042802412025X","DOIUrl":"10.1134/S107042802412025X","url":null,"abstract":"<p>A new compound, 2-amino-5-(4-bromophenyl)-5-{5-bromo-2-[(prop-2-en-1-yl)oxy]benzyl}-3,5-dihydro-4<i>H</i>-imidazol-4-one, has been synthesized by the reaction of (2<i>E</i>)-1-(4-bromophenyl)-3-{5-bromo-2-[(prop-2-en-1-yl)oxy]benzyl}prop-2-en-1-one with guanidine in the presence of hydrogen peroxide. The product structure was determined by NMR spectroscopy and X-ray analysis. A probable reaction mechanism has been proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2504 - 2507"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361992","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
Design and Synthesis of Novel Pyrazole-Based 1,2,3-Triazole Hybrids with Potent Cytotoxic Activity as Selective EGFR Kinase Inhibitors
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120170
K. Swapna, K. Deepthi, Ch. Sivudu, N. Kotilingaiah, B. Srinu, J. Sandhya
{"title":"Design and Synthesis of Novel Pyrazole-Based 1,2,3-Triazole Hybrids with Potent Cytotoxic Activity as Selective EGFR Kinase Inhibitors","authors":"K. Swapna,&nbsp;K. Deepthi,&nbsp;Ch. Sivudu,&nbsp;N. Kotilingaiah,&nbsp;B. Srinu,&nbsp;J. Sandhya","doi":"10.1134/S1070428024120170","DOIUrl":"10.1134/S1070428024120170","url":null,"abstract":"<p>A series of novel pyrazole-based 1,2,3-triazole hybrids <b>7a</b>–<b>7h</b> were synthesized and tested for in vitro cytotoxicity against MCF-7, IMR-32, HeLa, and HER293 cell lines. The compounds 1-(4-methylphenyl)-3-phenyl-1<i>H</i>-pyrazole-4-carbaldehyde <i>O</i>-[(1-phenyl-1<i>H</i>-1,2,3-triazol-5-yl)methyl]oxime (<b>7a</b>), 1-(4-bromo­phenyl)-3-phenyl-1<i>H</i>-pyrazole-4-carbaldehyde <i>O</i>-[(1-phenyl-1<i>H</i>-1,2,3-triazol-5-yl)methyl]oxime (<b>7e</b>), and 1-(4-nitrophenyl)-3-phenyl-1<i>H</i>-pyrazole-4-carbaldehyde <i>O</i>-[(1-phenyl-1<i>H</i>-1,2,3-triazol-5-yl)methyl]oxime (<b>7g</b>) displayed potential cytotoxic activity against the tested cell lines. The in silico molecular docking study of pyrazole-based 1,2,3-triazole hybrids <b>7a</b>–<b>7h</b> on the EGFR receptor revealed that compounds <b>7a</b>, <b>7e</b>, and<b> 7g</b> strongly bind to the protein, and the calculated binding energies were in excellent agreement with the corresponding IC<sub>50</sub> values.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2430 - 2438"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361996","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
Novel Straightforward One-Pot Synthesis and Characterization of 1-(2-Aminophenyl)-2,2,2-trifluoroethan-1-one Analogues
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120145
D. Kantheti, P. Kaur, J. V. Shanmukha Kumar
{"title":"Novel Straightforward One-Pot Synthesis and Characterization of 1-(2-Aminophenyl)-2,2,2-trifluoroethan-1-one Analogues","authors":"D. Kantheti,&nbsp;P. Kaur,&nbsp;J. V. Shanmukha Kumar","doi":"10.1134/S1070428024120145","DOIUrl":"10.1134/S1070428024120145","url":null,"abstract":"<p>An easy one-pot synthesis of 1-(2-aminophenyl)-2,2,2-trifluoroethan-1-one derivatives in an Inconel autoclave with 52–91% yields is reported. This protocol provides a very straightforward, quick, easy-to-work-up, and economical approach. <sup>1</sup>H, <sup>13</sup>C, <sup>19</sup>F NMR, 2D NMR, and LCMS were used to confirm the structure of the synthesized compounds. The compound C<sub>8</sub>H<sub>5</sub>ClF<sub>3</sub>NO (<b>3b</b>) exhibits a <i>syn</i> conformation for the F–C–C=O fragment with a torsion angle of 1.1(3)°. Additionally, there is an intramolecular N–H···O hydrogen bond that closes a six-membered ring. The molecules in crystal are connected into chains in the [010] direction by hydrogen bonds involving N–H···F and N–H···O interactions.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2411 - 2416"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361999","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 Oxidative Transformations of 5,7-Bis(4-methoxyphenyl)-1,2,3,4,4a,5-hexahydro-13H-benzimidazo[2,1-j]quinoline
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120078
L. N. Harchenko, K. V. Maslov, O. Yu. Slabko
{"title":"Synthesis and Oxidative Transformations of 5,7-Bis(4-methoxyphenyl)-1,2,3,4,4a,5-hexahydro-13H-benzimidazo[2,1-j]quinoline","authors":"L. N. Harchenko,&nbsp;K. V. Maslov,&nbsp;O. Yu. Slabko","doi":"10.1134/S1070428024120078","DOIUrl":"10.1134/S1070428024120078","url":null,"abstract":"<p>The reaction of 4,4′-dimethoxychalcone with cyclohexanone gave 1,5-diketone which was con­densed with <i>o</i>-phenylenediamine to produce 5,7-bis(4-methoxyphenyl)-1,2,3,4,4a,5-hexahydro-13<i>H</i>-benzimid­azo[2,1-<i>j</i>]quinoline. The oxidation and oxidative coupling of the latter with some primary amines and benzoylacetonitrile afforded fused heterocyclic <i>p</i>-quinoid compounds.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2356 - 2361"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362013","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
Visible Light Photoredox-Catalyzed Aerobic Oxidative Sulfonylation of Alkynes with Sodium Sulfinates: An Easy Access to β-Keto Sulfones
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120169
B. Yadav, S. K. Srivastava
{"title":"Visible Light Photoredox-Catalyzed Aerobic Oxidative Sulfonylation of Alkynes with Sodium Sulfinates: An Easy Access to β-Keto Sulfones","authors":"B. Yadav,&nbsp;S. K. Srivastava","doi":"10.1134/S1070428024120169","DOIUrl":"10.1134/S1070428024120169","url":null,"abstract":"<p>An efficient and green synthesis of β-keto sulfones by the reaction of alkynes and sodium sulfinates through a radical pathway using an organophotocatalyst is reported. The reaction was catalyzed by Eosin Y at room temperature involving air oxygen as clean and cheapest oxidant. The proposed protocol utilizes readily available sodium sulfinates as sulfonylating reagents and light as a cost-effective and environmentally benign energy source to offer a general approach for the synthesis of β-keto sulfones.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2422 - 2429"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362050","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, Characterization, and Antimicrobial Activity of 1,2,3-Triazoles Containing a Theophylline Moiety 含茶碱分子的 1,2,3-三唑的合成、表征和抗菌活性
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120182
M. V. Patel, D. J. Kaneriya
{"title":"Synthesis, Characterization, and Antimicrobial Activity of 1,2,3-Triazoles Containing a Theophylline Moiety","authors":"M. V. Patel,&nbsp;D. J. Kaneriya","doi":"10.1134/S1070428024120182","DOIUrl":"10.1134/S1070428024120182","url":null,"abstract":"<p>A new series of substituted 1,2,3-triazoles have been synthesized from theophylline and substituted 2-azido-<i>N</i>-phenylacetamides through copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction. The proposed method features minimal number of steps, high yields, straightforward conditions, and no need for further purification. The structures of the synthesized substituted 1,2,3–triazole derivatives were confirmed using spectral and analytical techniques. Their antimicrobial activity was tested in vitro, revealing that the nature of the substituents on the triazole ring significantly influences antimicrobial efficacy, as demonstrated by a preliminary structure–activity relationship analysis.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2439 - 2445"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362051","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
Benzimidazole Derivatives as Potential CDK2 Inhibitors: Synthesis, Molecular Docking, and Antiproliferative Investigations
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120212
Ranza Elrayess, Ranwa Elrayess, Khaled Hussien, Nagat Ghareb
{"title":"Benzimidazole Derivatives as Potential CDK2 Inhibitors: Synthesis, Molecular Docking, and Antiproliferative Investigations","authors":"Ranza Elrayess,&nbsp;Ranwa Elrayess,&nbsp;Khaled Hussien,&nbsp;Nagat Ghareb","doi":"10.1134/S1070428024120212","DOIUrl":"10.1134/S1070428024120212","url":null,"abstract":"<p>From numerous threats, malignancies are outstanding as one of the most hazardous diseases facing human life in the current time. Thus, novel medicines that selectively target tumor cells will inevitably add to the therapeutic arsenal already possessed for curing these malignancies. In light of this, the current study strives to create a novel class of small compounds with the advantageous benzimidazole scaffold that may be used as CDK2 inhibitors versus cancer. The synthesized candidates <b>2a</b>–<b>2c</b> and <b>4</b> markedly impeded the development of the four cell lines under investigation with IC<sub>50</sub> values of 4.36 ± 0.27 to 11.54 ± 0.29 μM against MCF-7, 9.48 ± 0.28 to 25.94 ± 0.33 μM against HCT-15, 41.76 ± 0.76 to 70.61 ± 1.45 against K-562, and 15.04 ± 0.70 to 32.38 ± 1.13 against HepG2. Moreover, compounds <b>2a</b>–<b>2c</b> and <b>4</b> showed robust CDK2 inhibitory effect (IC<sub>50</sub> = 0.76 ± 0.28, 1.26 ± 0.049, 0.84 ± 0.075, and 1.37 ± 0.062 μM, respectively). In order to assess the selectivity towards cancer cells, their cytotoxicity against normal kidney epithelial cells Vero was evaluated. The examined compounds were found to be more selective toward cancer cells when compared to the reference standard (SI = 2.13), and compound <b>2a</b> demonstrated higher selectivity for the breast cancer MCF-7 cell line with the highest selectivity index (SI = 14.98), followed by compound <b>2c</b> (SI = 8.42). Ultimately, a molecular docking study was performed to examine the potential binding pattern and interactions of benzimidazole derivatives with CDK2 kinase, suggesting it as an enzymatic target. In the final result, benzimidazole derivatives <b>2a</b>–<b>2c</b> and <b>4</b>, especially compound <b>2a</b>, showed significant anticancer efficacy in addition to their ability to inhibit CDK2.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2462 - 2474"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143362046","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 4,13-Dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diyl Bis[3(4)-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoates]
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120066
O. A. Kolyamshin, Yu. N. Mitrasov, V. A. Danilov
{"title":"Synthesis of 4,13-Dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diyl Bis[3(4)-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoates]","authors":"O. A. Kolyamshin,&nbsp;Yu. N. Mitrasov,&nbsp;V. A. Danilov","doi":"10.1134/S1070428024120066","DOIUrl":"10.1134/S1070428024120066","url":null,"abstract":"<p>New bis-carbamates, 4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diyl bis[3(4)-aminoben­zoates], were synthesized by the reaction of bis(2-chloroethyl) hexane-1,6-diyldicarbamate with potassium 3- and 4-aminobenzoates. These compounds reacted with maleic anhydride at a ratio of 1:2 to give the corre­sponding bis-maleamic acids which were cyclized in acidic medium to afford 4,13-dioxo-3,14-dioxa-5,12diaza­hexa­decane-1,16-diyl bis[3(4)-(2,5-dioxo-2,5-dihydro-1<i>H</i>-pyrrol-1-yl)benzoates]. Physical and spectral properties of the obtained bis-maleimides were studied.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2351 - 2355"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1134/S1070428024120066.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361959","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
Highly Efficient Synthesis of 1,3,5-Oxadiazinan-4-one and 5-Methyl-1,3,5-triazinan-2-one Derivatives of Benzimidazolyl Pyrimidine and Their Activity Analysis through Docking Studies
IF 0.8 4区 化学
Russian Journal of Organic Chemistry Pub Date : 2025-02-06 DOI: 10.1134/S1070428024120194
S. Patolla, S. Kethireddy, B. Pittala, L. Eppakayala, S. R. Bireddy
{"title":"Highly Efficient Synthesis of 1,3,5-Oxadiazinan-4-one and 5-Methyl-1,3,5-triazinan-2-one Derivatives of Benzimidazolyl Pyrimidine and Their Activity Analysis through Docking Studies","authors":"S. Patolla,&nbsp;S. Kethireddy,&nbsp;B. Pittala,&nbsp;L. Eppakayala,&nbsp;S. R. Bireddy","doi":"10.1134/S1070428024120194","DOIUrl":"10.1134/S1070428024120194","url":null,"abstract":"<p>4-(1<i>H</i>-Benzimidazol-2-yl)-6-phenylpyrimidin-2-yl-substituted 1,3,5-oxadiazinan-4-one and 5-methyl-1,3,5-triazinan-2-one derivatives were synthesized from <i>N</i>-[4-(1<i>H</i>-benzimidazol-2-yl)-6-phenyl­pyrimidin-2-yl]-<i>N</i>′-aryl ureas, and their structure was confirmed by NMR and mass spectroscopic techniques. Some of the synthesized derivatives were analyzed for their binding affinity for EGFR through molecular docking studies.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 12","pages":"2446 - 2453"},"PeriodicalIF":0.8,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143361995","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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