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The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine 1,4-dioxides. 5- 芳基-2,3-二氢吡嗪-1,4-二氧化物的光化学行为研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-19 DOI: 10.1039/d4ob01570c
Nadezhda A Bakuleva, Boris V Lichitskii, Andrey N Komogortsev, Evgeny V Tretyakov
{"title":"The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine 1,4-dioxides.","authors":"Nadezhda A Bakuleva, Boris V Lichitskii, Andrey N Komogortsev, Evgeny V Tretyakov","doi":"10.1039/d4ob01570c","DOIUrl":"https://doi.org/10.1039/d4ob01570c","url":null,"abstract":"<p><p>For the first time, the photochemical behavior of aryl-substituted 2,3-dihydropyrazine 1,4-dioxides was investigated. A common feature of all observed photoprocesses is the conversion of nitrone moieties into an oxaziridine ring to give substituted bi- or polycyclic systems. It was shown that the direction of the reaction depends on the irradiation wavelength and the employed solvent. For instance, the use of 365 nm UV light leads to the cyclization of both nitrone moieties. In contrast, visible-light irradiation (450 nm) allows one to regiospecifically utilize an aldonitrone unit to form 7-oxa-1,4-diazabicyclo[4.1.0]hept-4-ene 4-oxide derivatives. Generally, the oxaziridine ring possesses high reactivity and can be transformed <i>in situ</i> by various reagents. The molecular and crystal structures of the representatives of both bicyclic systems were solved for the first time with X-ray diffraction analysis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666661","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Mechanochemically facilitated silver-catalyzed direct H/D exchange on heteroarenes. 机械化学促进银催化杂环戊烯的直接 H/D 交换。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-19 DOI: 10.1039/d4ob01581a
Yun Jia, Zhi-Jiang Jiang, Jiawei Han, Kenan Wang, Si-Han Xu, Jian-Fei Bai, Jia Chen, Yifeng Han, Zhanghua Gao
{"title":"Mechanochemically facilitated silver-catalyzed direct H/D exchange on heteroarenes.","authors":"Yun Jia, Zhi-Jiang Jiang, Jiawei Han, Kenan Wang, Si-Han Xu, Jian-Fei Bai, Jia Chen, Yifeng Han, Zhanghua Gao","doi":"10.1039/d4ob01581a","DOIUrl":"https://doi.org/10.1039/d4ob01581a","url":null,"abstract":"<p><p>Despite recent advances in H/D exchange, the effective deuteration of polyarenes remains challenging, due to their insolubility and hydrophobicity. This study presents a concept proofing of a mechanochemically facilitated direct H/D exchange. The silver-catalyzed deuteration of heteroarenes was promoted smoothly within 99 minutes of grinding, with heavy water as the deuterium source.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666659","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Pd-catalyzed ortho-/meta-C-H-annulation of biphenyl amines with enynes through non-rollover cyclometallation. 通过非翻转环金属化，Pd 催化联苯胺与炔烃的正交/正交-C-H-annulation。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-18 DOI: 10.1039/d4ob01689k
Undamatla Suri Babu, Muniganti Naveen Kumar, Shivunapuram Mahesh, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
{"title":"Pd-catalyzed <i>ortho</i>-/<i>meta</i>-C-H-annulation of biphenyl amines with enynes through non-rollover cyclometallation.","authors":"Undamatla Suri Babu, Muniganti Naveen Kumar, Shivunapuram Mahesh, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy","doi":"10.1039/d4ob01689k","DOIUrl":"https://doi.org/10.1039/d4ob01689k","url":null,"abstract":"<p><p>Annulations through dual C-H activation represent a powerful tool to selectively assemble multi-cyclic scaffolds. We present herein a palladium-catalyzed <i>ortho</i>-/<i>meta</i>-C-H-annulation of biphenyl amines with 1,6-enynes. This regioselective non-rollover cyclometallation was achieved through meticulous tuning of electronic factors of both the partners. This method is applicable to a wide range of protected <i>o</i>-arylanilines and enynes, and results in the regioselective preparation of benzo[<i>f</i>]isoindolyl derivatives in high yields with good diastereoselectivity (with respect to two types of stereogenic elements). Certain essential control experiments and kinetic isotope effect (KIE) studies were undertaken to elucidate the reaction mechanism, while subsequent transformations and a scale-up reaction were performed to substantiate the sturdiness of the transformation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646147","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
TFAA mediated one-pot synthesis of chiral N-protected amino acid-derived 1,2,4-oxadiazoles and their antibacterial studies. TFAA 介导的手性 N 保护氨基酸衍生 1,2,4-恶二唑的单锅合成及其抗菌研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-18 DOI: 10.1039/d4ob01509f
Srinivasan Pon Saravanakumar, Nagarajan Nagasundaram, Jayaraman DhineshKumar, Periyaswamy Rajalakshmi, Appaswami Lalitha
{"title":"TFAA mediated one-pot synthesis of chiral <i>N</i>-protected amino acid-derived 1,2,4-oxadiazoles and their antibacterial studies.","authors":"Srinivasan Pon Saravanakumar, Nagarajan Nagasundaram, Jayaraman DhineshKumar, Periyaswamy Rajalakshmi, Appaswami Lalitha","doi":"10.1039/d4ob01509f","DOIUrl":"https://doi.org/10.1039/d4ob01509f","url":null,"abstract":"<p><p>A scalable and environment-friendly one-pot two-component synthesis of chiral <i>N</i>-protected amino acid substituted 1,2,4-oxadiazoles from hydroxyl amidine and (<i>S</i>)-2-(2,2,2-trifluoroacetamido)propanoic 2,2,2-trifluoroacetic anhydride is described. This operationally simple methodology affords an efficient and convenient solution to synthesize chiral <i>N</i>-protected amino acids under catalyst-free conditions. All the synthesized compounds were screened for their <i>in vitro</i> antibacterial activity towards six human pathogenic bacterial species, among which, 4al exhibited a significant efficacy against <i>Escherichia coli</i> with the MIC value of 0.19 μg mL<sup>-1</sup>.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646149","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
NMR and molecular simulation studies on the structure elucidation of the amphotericin B ion channel using 13C and 19F labelling. 利用 13C 和 19F 标记阐明两性霉素 B 离子通道结构的核磁共振和分子模拟研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-18 DOI: 10.1039/d4ob01468e
Yuichi Umegawa, Hiroshi Tsuchikawa, Wataru Shinoda, Michio Murata
{"title":"NMR and molecular simulation studies on the structure elucidation of the amphotericin B ion channel using <sup>13</sup>C and <sup>19</sup>F labelling.","authors":"Yuichi Umegawa, Hiroshi Tsuchikawa, Wataru Shinoda, Michio Murata","doi":"10.1039/d4ob01468e","DOIUrl":"https://doi.org/10.1039/d4ob01468e","url":null,"abstract":"<p><p>Amphotericin B (AmB) has been clinically used for serious fungal infections for over 60 years. The drug is characterized by its specific recognition of ergosterol (Erg) in the fungal cell membrane. AmB and Erg form an ion-channel assembly, which is thought to play a major role in the antibiotic activity of AmB. The precise structure of the ion channel in fungal membranes still remains unelucidated. Recently, the structure of an AmB assembly formed in artificial lipid bilayers was determined using solid-state NMR and molecular dynamics simulations. The structure elucidation was made possible by using <sup>13</sup>C- and <sup>19</sup>F-labelled AmBs, which were efficiently synthesized using strategies and methods established in previous studies. This review focuses on the structure of the AmB ion channel, which accounts for the antibiotic activity. Additionally, the chemical syntheses of isotope-labelled AmB and Erg used for the structural studies are also reviewed. Solid-state NMR spectra of the labelled AmBs were recorded to measure the distances between labelled sites in the AmB-Erg assembly in lipid bilayers, revealing that the ion channel consisting of seven molecules of AmB spans the bilayer with a single molecule length. Extensive molecular dynamics simulations showed that the conductance of this AmB channel is comparable with those by single-channel recording. The simulations also demonstrated that Erg stabilizes the ion-channel assemblies more efficiently than human cholesterol. The atomic-level structure of the AmB channel in the artificial bilayer will help us to understand the mechanisms of the pharmacological actions and adverse effects of AmB.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646145","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photooxidative C-C double bond cleavage of β-enaminocarbonyl compounds: toward selective N-formylation of amines. β-烯氨基羰基化合物的光氧化 C-C 双键裂解：实现胺的选择性 N-甲酰化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-15 DOI: 10.1039/d4ob01688b
Hayeon You, Suk Hyun Lim, Dae Won Cho
{"title":"Photooxidative C-C double bond cleavage of β-enaminocarbonyl compounds: toward selective <i>N</i>-formylation of amines.","authors":"Hayeon You, Suk Hyun Lim, Dae Won Cho","doi":"10.1039/d4ob01688b","DOIUrl":"10.1039/d4ob01688b","url":null,"abstract":"<p><p>A photooxidative C-C double bond cleavage of electron-deficient β-enaminocarbonyl compounds possessing a silyl group at the α-position to the nitrogen atom using methylene blue (MB) as the photosensitizer was explored. Photochemically generated <sup>1</sup>O<sub>2</sub> was added across the CC bond with the aid of a tethered silyl group to cleave it and form <i>N</i>-formylamines. This reaction protocol exhibited compatibility with numerous β-enaminocarbonyl substrates, including those with various <i>N</i>-alkyl, <i>N</i>-benzyl and <i>N</i>-aryl substituents.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142611421","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Alkyl groups in organic molecules are NOT inductively electron-releasing. 有机分子中的烷基不会感应释放电子。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-15 DOI: 10.1039/d4ob01572j
Mark C Elliott, Colan E Hughes, Peter J Knowles, Benjamin D Ward
{"title":"Alkyl groups in organic molecules are NOT inductively electron-releasing.","authors":"Mark C Elliott, Colan E Hughes, Peter J Knowles, Benjamin D Ward","doi":"10.1039/d4ob01572j","DOIUrl":"10.1039/d4ob01572j","url":null,"abstract":"<p><p>It is commonly stated that alkyl groups exert an inductive electron-releasing effect when compared to hydrogen. This information has been given in numerous organic chemistry textbooks over the last 75 years. The evidence for this position is weak, and does not withstand scrutiny, and there is some evidence for the contrary position. We provide a significant body of computational data that clearly show that alkyl groups exert an inductive electron-withdrawing (-I) effect when compared to hydrogen. This revised position is not in conflict with experimental data, since alkyl group inductive effects are small and are likely to be masked by hyperconjugation/polarizability effects (particularly in charged species), and also by solvent effects.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612974","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Recent advances in the transformation of maleimides via annulation. 通过环化转化马来酰亚胺的最新进展。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-15 DOI: 10.1039/d4ob01632g
Mohammad Aslam, Muhammad Saeed Akhtar, Hee Nam Lim, Jeong Hyun Seo, Yong Rok Lee
{"title":"Recent advances in the transformation of maleimides <i>via</i> annulation.","authors":"Mohammad Aslam, Muhammad Saeed Akhtar, Hee Nam Lim, Jeong Hyun Seo, Yong Rok Lee","doi":"10.1039/d4ob01632g","DOIUrl":"https://doi.org/10.1039/d4ob01632g","url":null,"abstract":"<p><p>Over the past five years, maleimide scaffolds have gained considerable attention in organic synthesis for their role in forming cyclized molecules through annulation and C-H activation. As versatile and reactive coupling agents, maleimides have enabled the efficient synthesis of various cyclized products, including annulation, benzannulation, cycloaddition, and spirocyclization, with applications in medicinal chemistry, drug discovery, and materials science. Despite the extensive study of maleimide chemistry, certain reactions-such as cycloaddition-based annulation, photoannulation, and electrochemical transformations-remain underexplored despite their promising potential in the pharmaceutical and chemical industries. Recent advancements, such as photocatalysis and electrochemical methods, have expanded the utility of maleimides, providing more sustainable and selective approaches for synthesizing complex molecules. This review compiles research published between 2019 and 2024, highlighting the substrate scope, reaction diversity, and industrial relevance of maleimide-based annulation strategies. Additionally, we discuss emerging trends and future directions in maleimide chemistry, exploring opportunities for novel reaction pathways and broader applications in synthetic biology and materials science.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Expeditious synthesis of CF3-phenanthridones through a base-mediated cross-conjugated vinylogous benzannulation (VBA). 通过碱介导的交叉共轭乙烯基苯并吡喃反应 (VBA) 快速合成 CF3-菲啶酮。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-15 DOI: 10.1039/d4ob01480d
Madhu Desagoni, Chavakula Nagababu, Nagender Punna
{"title":"Expeditious synthesis of CF<sub>3</sub>-phenanthridones through a base-mediated cross-conjugated vinylogous benzannulation (VBA).","authors":"Madhu Desagoni, Chavakula Nagababu, Nagender Punna","doi":"10.1039/d4ob01480d","DOIUrl":"https://doi.org/10.1039/d4ob01480d","url":null,"abstract":"<p><p>Herein, we report a mild, efficient, and rapid approach for the preparation of CF<sub>3</sub>-phenanthridones through a cross-conjugated vinylogous [4 + 2] benzannulation of easily accessible 4-methyl-3-trifluoroacetylquinolones and nitro-olefins. The present transformation is superior to previous approaches for obtaining CF<sub>3</sub>-phenanthridones, in that it proceeds exclusively with the assistance of a simple base, eliminating the need for transition metal catalysts or oxidants. The strong electron-withdrawing nature of the CF<sub>3</sub>-group present in the quinolone moiety promotes the formation of a reactive cross-conjugated vinylogous enolate.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637944","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Efficient synthesis of promising antidiabetic triazinoindole analogues via a solvent-free method: investigating the reaction of 1,3-diketones and 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione. 通过无溶剂方法高效合成有前景的抗糖尿病三嗪吲哚类似物：研究 1,3- 二酮和 2,5- 二氢-3H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫酮的反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-14 DOI: 10.1039/d4ob01487a
Ranjana Aggarwal, Prince Kumar, Mona Hooda, Rahul Singh, Parvin Kumar
{"title":"Efficient synthesis of promising antidiabetic triazinoindole analogues <i>via</i> a solvent-free method: investigating the reaction of 1,3-diketones and 2,5-dihydro-3<i>H</i>-[1,2,4]triazino[5,6-<i>b</i>]indole-3-thione.","authors":"Ranjana Aggarwal, Prince Kumar, Mona Hooda, Rahul Singh, Parvin Kumar","doi":"10.1039/d4ob01487a","DOIUrl":"https://doi.org/10.1039/d4ob01487a","url":null,"abstract":"<p><p>Diabetes poses a significant global health challenge, driving the search for effective management strategies. In the past years, α-amylase inhibitors have emerged as promising candidates for regulating blood sugar levels. In this concern, we have synthesized a series of novel 3-methyl-2-aroylthiazolo[3',2':2,3][1,2,4]triazino[5,6-<i>b</i>]indole derivatives <i>via</i> the regioselective reaction of 2,5-dihydro-3<i>H</i>-[1,2,4]triazino[5,6-<i>b</i>]indole-3-thione and 1,3-diketones in the presence of NBS under solvent-free conditions. Subsequently, the inhibitory potential of the newly synthesized 3-methyl-2-aroylthiazolo[3',2':2,3][1,2,4]triazino[5,6-<i>b</i>]indole derivatives was assessed against the α-amylase enzyme to probe their antidiabetic properties. <i>In vitro</i> studies revealed moderate to excellent α-amylase inhibitory activity, with IC<sub>50</sub> values ranging from 16.14 ± 0.41 to 27.69 ± 0.58 μg ml<sup>-1</sup>. Furthermore, SAR analysis showed that compounds containing halogen groups exhibited superior inhibition potential, surpassing the standard drug Acarbose (IC<sub>50</sub> = 18.64 ± 0.42 μg ml<sup>-1</sup>), particularly derivatives substituted with 4-fluoro and 2,4-dichloro groups, with IC<sub>50</sub> values of 16.14 ± 0.41 μg ml<sup>-1</sup> and 17.21 ± 0.15 μg ml<sup>-1</sup>, respectively. Additionally, molecular docking unveiled the binding modes of ligands with the active site of <i>A. oryzae</i> α-amylase. Encouragingly, the theoretical analyses closely mirrored the experimental findings, further underlining the promise of these synthetic molecules as potent α-amylase inhibitors.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142613089","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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