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Effects of acid-mediated deamination of cytidine and 5-methylcytidine on solid-phase synthesis of oligonucleotides 酸介导胞苷和5-甲基胞苷脱胺对固相合成寡核苷酸的影响
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-21 DOI: 10.1016/j.tet.2025.134840
Yusuke Isono , Chihiro Karasugi , Takuya Akisawa , Takashi Osawa , Qin Ren , Michiaki Tatsuno , Fumi Ito , Takao Inoue , Junji Kawakami , Satoshi Obika , Masaki Shinoda
{"title":"Effects of acid-mediated deamination of cytidine and 5-methylcytidine on solid-phase synthesis of oligonucleotides","authors":"Yusuke Isono ,&nbsp;Chihiro Karasugi ,&nbsp;Takuya Akisawa ,&nbsp;Takashi Osawa ,&nbsp;Qin Ren ,&nbsp;Michiaki Tatsuno ,&nbsp;Fumi Ito ,&nbsp;Takao Inoue ,&nbsp;Junji Kawakami ,&nbsp;Satoshi Obika ,&nbsp;Masaki Shinoda","doi":"10.1016/j.tet.2025.134840","DOIUrl":"10.1016/j.tet.2025.134840","url":null,"abstract":"<div><div>Oligonucleotide therapeutics have attracted considerable attention in recent years as a new drug discovery modality. They are generally produced via solid-phase oligonucleotide synthesis based on phosphoramidite chemistry. Oligonucleotide therapeutics form Watson–Crick base pairs with the target RNA and strictly recognize their sequence for gene regulation; therefore, structural changes in nucleobases could be crucial and should be avoided during oligonucleotide synthesis. In this study, we investigated the deamination of cytidine and 5-methylcytidine during the acid-mediated removal of dimethoxytrityl (DMTr) group of solid-phase oligonucleotide synthesis. Our results suggest that the deamination reaction proceeds regardless of the structure of the sugar moiety of the phosphoramidite monomer, particularly in reaction systems containing more than 1 % of water. The data from this study is believed highly beneficial and helpful for avoiding acid-mediated deamination of cytidine and 5-methylcytidine during oligonucleotide synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134840"},"PeriodicalIF":2.2,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144721121","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
Mechanosynthesis of N-heterocyclic compounds via ball milling 球磨法机械合成n -杂环化合物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-21 DOI: 10.1016/j.tet.2025.134842
Lei Wang , Ye Zhang , Hui Xu , Ze Zhang
{"title":"Mechanosynthesis of N-heterocyclic compounds via ball milling","authors":"Lei Wang ,&nbsp;Ye Zhang ,&nbsp;Hui Xu ,&nbsp;Ze Zhang","doi":"10.1016/j.tet.2025.134842","DOIUrl":"10.1016/j.tet.2025.134842","url":null,"abstract":"<div><div>Mechanochemistry, an emerging synthetic strategy that utilizes mechanical forces to drive chemical transformations, has attracted significant attention due to its advantages of solvent minimization, high efficiency, and environmental sustainability. Unlike conventional solution-based methods, mechanochemical transformations are driven by friction, shear, and impact generated by mechanical energy, offering unique opportunities for accessing novel reactions and materials. Diverse techniques, including grinding, extrusion, and ball milling, have been extensively employed in organic synthesis, materials science, and pharmaceuticals, and a number of relevant review articles have been published covering a large variety of achievements over the past two decades. This review specifically focuses on the application of ball milling in the construction of nitrogen-containing heterocyclic small molecules, many of which are pivotal structural motifs in pharmaceuticals, bioactive molecules, functional materials, and fine chemicals. By highlighting representative examples and future prospects, this review aims to inspire further innovations in sustainable synthetic methodologies and broaden the scope of mechanochemistry in heterocyclic chemistry.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134842"},"PeriodicalIF":2.1,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144696811","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
The many faces of (R∗)-4-[(S∗)-1-methanesulfonyloxypropyl]-3-methoxy-1,3-oxazinane （R∗）-4-[(S∗)-1-甲磺酰基氧丙基]-3-甲氧基-1,3-恶嗪烷的许多面
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-19 DOI: 10.1016/j.tet.2025.134847
Robert A. Pascal Jr. , Sarah A. Neuenswander , Justin T. Douglas , Mohammad R. Mian , Shyam Sathyamoorthi
{"title":"The many faces of (R∗)-4-[(S∗)-1-methanesulfonyloxypropyl]-3-methoxy-1,3-oxazinane","authors":"Robert A. Pascal Jr. ,&nbsp;Sarah A. Neuenswander ,&nbsp;Justin T. Douglas ,&nbsp;Mohammad R. Mian ,&nbsp;Shyam Sathyamoorthi","doi":"10.1016/j.tet.2025.134847","DOIUrl":"10.1016/j.tet.2025.134847","url":null,"abstract":"<div><div>The <sup>1</sup>H NMR spectrum of (<em>R∗</em>)-4-[(<em>S∗</em>)-1-methanesulfonyloxypropyl]-3-methoxy-1,3-oxazinane (<strong>3</strong>) is incomprehensible at room temperature due to line broadening from the dynamic exchange of many conformations. VT-NMR studies show two equal populations at low temperatures. As the temperature increases, they coalesce into a single population with a free energy of activation for this process of 14.0–14.6 kcal/mol. DFT studies indicate that each of the low-temperature populations is a collection of rapidly interconverting species, and the critical barrier to interconversion is an inversion at nitrogen in compound <strong>3</strong> with calculated barriers of 14.3–16.0 kcal/mol, depending on the computational method employed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134847"},"PeriodicalIF":2.1,"publicationDate":"2025-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144679375","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
Progress in the synthesis and applications of FDA-approved anticancer drugs: Current trends and future perspectives fda批准的抗癌药物的合成和应用进展：当前趋势和未来展望
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-19 DOI: 10.1016/j.tet.2025.134833
Javed Khan , Anjali Rani , Sushant Sharma , Garima Pandey , Bhaskara Nand
{"title":"Progress in the synthesis and applications of FDA-approved anticancer drugs: Current trends and future perspectives","authors":"Javed Khan ,&nbsp;Anjali Rani ,&nbsp;Sushant Sharma ,&nbsp;Garima Pandey ,&nbsp;Bhaskara Nand","doi":"10.1016/j.tet.2025.134833","DOIUrl":"10.1016/j.tet.2025.134833","url":null,"abstract":"<div><div>Cancer is the primary obstacle to increasing life expectancy worldwide in the 21st century. It is a big global public health condition that poses a substantial challenge. Considerable advancements have been made in anticancer drug development over recent decades, producing numerous new agents derived from both natural and synthetic sources. Both chemotherapy and small-molecule targeted treatment are considered to be two of the most fundamental techniques of treating cancer, both of which include chemical agents. This review aims to overview the structures, approval status, application and synthesis of FDA-approved anticancer drugs from 1997 to 2024. To encourage the production of new, efficient and applicable synthetic procedures, we seek to provide a thorough explanation of the synthetic approaches used to create these therapeutic compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134833"},"PeriodicalIF":2.1,"publicationDate":"2025-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144679373","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
Magnesium-catalyzed hydrophosphination of alkenes and alkynes 镁催化烯烃和炔烃的氢磷化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-19 DOI: 10.1016/j.tet.2025.134849
Yongxin Feng, Xiaofei Rong, Xuguang Zhang, Yukang He, Mengtao Ma
{"title":"Magnesium-catalyzed hydrophosphination of alkenes and alkynes","authors":"Yongxin Feng,&nbsp;Xiaofei Rong,&nbsp;Xuguang Zhang,&nbsp;Yukang He,&nbsp;Mengtao Ma","doi":"10.1016/j.tet.2025.134849","DOIUrl":"10.1016/j.tet.2025.134849","url":null,"abstract":"<div><div>The hydrophosphination of alkenes and alkynes catalyzed by simple commercially available magnesium reagent was reported. A range of alkenes were converted to the corresponding <em>anti</em>-Markovnikov alkylphosphine products in high yields and high regioselectivity under the presence of 10 mol% Grignard reagent MeMgI at room temperature. Meanwhile, the hydrophosphination of various alkynes was catalyzed by 10 mol% <sup>n</sup>Bu<sub>2</sub>Mg to afford the corresponding <em>anti</em>-Markovnikov <em>Z</em>-alkenylphosphines with high yields and excellent regioselectivity. Scale-up reaction show great potential in practical applications.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134849"},"PeriodicalIF":2.1,"publicationDate":"2025-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144672089","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
HFIP-triggered C3-hydroalkylation of imidazo[1,2-a]pyridines with maleimides hfip触发咪唑[1,2-a]吡啶与马来酰亚胺的c3 -氢烷基化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-18 DOI: 10.1016/j.tet.2025.134844
Juanjuan Gao , Xinlei Fu , Xue Zhu , Shuqin Yu , LongHui Wu , Xinyuan Liao , Kai Yang , Yifan Cao
{"title":"HFIP-triggered C3-hydroalkylation of imidazo[1,2-a]pyridines with maleimides","authors":"Juanjuan Gao ,&nbsp;Xinlei Fu ,&nbsp;Xue Zhu ,&nbsp;Shuqin Yu ,&nbsp;LongHui Wu ,&nbsp;Xinyuan Liao ,&nbsp;Kai Yang ,&nbsp;Yifan Cao","doi":"10.1016/j.tet.2025.134844","DOIUrl":"10.1016/j.tet.2025.134844","url":null,"abstract":"<div><div>Herein, a facile HFIP-triggered C(sp<sup>2</sup>)-H hydroalkylation of imidazo[1,2-<em>a</em>]pyridines with maleimides via Michael addition process has been described. A series of C3-succinylated imidazo[1,2-<em>a</em>]pyridines were prepared in moderate to good yields in the absence of transition metals. The protocol was characterized by simple operation, a broad substrate scope, and scale-up synthesis. Furthermore, the synthesized target compounds also have the potential for further derivatization to obtain more biologically active compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134844"},"PeriodicalIF":2.1,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144672091","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
Syntheses of natural and non-natural β-amino acids using racemic and enantioselective sulfamate-tethered aza-Michael cyclization reactions 利用外消旋和对映选择性磺胺酸拴链aza-Michael环化反应合成天然和非天然β-氨基酸
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-18 DOI: 10.1016/j.tet.2025.134845
Mintu Munda, Harshit Joshi, Shyam Sathyamoorthi
{"title":"Syntheses of natural and non-natural β-amino acids using racemic and enantioselective sulfamate-tethered aza-Michael cyclization reactions","authors":"Mintu Munda,&nbsp;Harshit Joshi,&nbsp;Shyam Sathyamoorthi","doi":"10.1016/j.tet.2025.134845","DOIUrl":"10.1016/j.tet.2025.134845","url":null,"abstract":"<div><div>We detail the preparation of a library of ten β-amino acids (7 racemic and 3 scalemic), highlighting our laboratory's racemic and enantioselective sulfamate-tethered <em>aza</em>-Michael cyclization reactions. All ten syntheses proceed from oxathiazinane heterocycles furnished by reactions invented in our laboratory. This work raises the prominence of sulfamate-tethered <em>aza</em>-Michael technology and advocates for the more general use of sulfamates in olefin functionalization processes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134845"},"PeriodicalIF":2.1,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144696812","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
Fe-catalyzed sp3-sp3 coupling enabled by hydrofunctionalizations of alkenes 烯烃加氢官能化使铁催化的sp3-sp3偶联成为可能
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-18 DOI: 10.1016/j.tet.2025.134835
Lan Tian , Muneer-ul-Shafi Bhat , Xiao-Yi Chen , Yu-Long Li , Wei Shu
{"title":"Fe-catalyzed sp3-sp3 coupling enabled by hydrofunctionalizations of alkenes","authors":"Lan Tian ,&nbsp;Muneer-ul-Shafi Bhat ,&nbsp;Xiao-Yi Chen ,&nbsp;Yu-Long Li ,&nbsp;Wei Shu","doi":"10.1016/j.tet.2025.134835","DOIUrl":"10.1016/j.tet.2025.134835","url":null,"abstract":"<div><div>Transition-metal-catalyzed hydrofunctionalizations of alkenes are emerging as an enabling technique for carbon-carbon and carbon-heteroatom bond formation, providing a powerful alternative to build saturated carbon centers. To this end, Fe-catalyzed hydrofunctionalizations of alkenes offer a great opportunity for <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> cross-coupling event. Metal-hydrogen atom transfer (MHAT) from iron hydride to alkenes enables alkenes as reliable alkyl radical precursors, followed by coupling with different <em>sp</em><sup>3</sup> coupling partners to forge a myriad of <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> bonds. This reaction circumvents the use of stoichiometric <em>sp</em><sup>3</sup> nucleophiles for <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> cross-coupling, featuring the <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> coupling from alkenes. This review summarizes the development and mechanistic understanding of Fe-catalyzed <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> coupling by hydrofunctionalization of alkenes. Further consideration on this area for new reaction development and orientations are discussed. We hope this review will provide insight into this iron-catalyzed reaction mode to forge <em>sp</em><sup>3</sup>-<em>sp</em><sup>3</sup> bonds from alkenes in the presence of nucleophiles and inspire new thoughts and efforts to this area.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134835"},"PeriodicalIF":2.1,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144686126","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
Potassium ferricyanide-mediated regioselective cross-dehydrogenative coupling of catechols with 2-oxindoles and benzofuranones 铁氰化钾介导的儿茶酚与2-吲哚和苯并呋喃酮的区域选择性交叉脱氢偶联
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-17 DOI: 10.1016/j.tet.2025.134831
Tomoyuki Iwakiri , Mai Akakabe , Akifumi Inoue , Yoshihiro Sohtome , Mikiko Sodeoka
{"title":"Potassium ferricyanide-mediated regioselective cross-dehydrogenative coupling of catechols with 2-oxindoles and benzofuranones","authors":"Tomoyuki Iwakiri ,&nbsp;Mai Akakabe ,&nbsp;Akifumi Inoue ,&nbsp;Yoshihiro Sohtome ,&nbsp;Mikiko Sodeoka","doi":"10.1016/j.tet.2025.134831","DOIUrl":"10.1016/j.tet.2025.134831","url":null,"abstract":"<div><div>Cross dehydrogenative coupling (CDC) reactions of catechols offer a direct route to multi-substituted catechols. While <em>in situ</em> oxidation to <em>ortho</em>-quinones has advanced CDC reactions of catechols, controlling regioselectivity remains challenging. Herein, we present details of our investigations into the C(6)-selective CDC reaction of 4-substituted catechols with the persistent radical precursors, 2-oxindoles and benzofuranones. Our optimization studies, based on mechanistic control experiments, led to the development of a cooperative oxidation system using dissolved O<sub>2</sub> and a sub-stoichiometric amount of K<sub>3</sub>[Fe(CN)<sub>6</sub>], which expands the substrate scope of the C(6)-selective CDC reaction of 4-substituted catechols.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134831"},"PeriodicalIF":2.1,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144696813","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
Tailoring sulfoxidation: Multifaceted role of manganese porphyrins 裁剪亚砜化：锰卟啉的多方面作用
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-17 DOI: 10.1016/j.tet.2025.134837
Thasnim P Mohammed , Mohammed Shinan , Muniyandi Sankaralingam
{"title":"Tailoring sulfoxidation: Multifaceted role of manganese porphyrins","authors":"Thasnim P Mohammed ,&nbsp;Mohammed Shinan ,&nbsp;Muniyandi Sankaralingam","doi":"10.1016/j.tet.2025.134837","DOIUrl":"10.1016/j.tet.2025.134837","url":null,"abstract":"<div><div>In the current era of industrialization, catalytic oxidation processes play a pivotal role in synthesizing both fine and bulk chemicals. Various strategies have been employed using different metal complexes as catalysts to enhance efficiency and selectivity. In this context, extensive studies have been conducted on the oxidation of sulfur to sulfoxides and sulfones, utilizing diverse catalytic systems that are not only highly selective but also environmentally benign, in contrast to traditional methods that rely on harsh reaction conditions. The oxidized sulfur products remain a topic of great interest due to their widespread applications in medicinal chemistry, drug metabolism, and pharmaceutical industries. Among the different catalytic systems explored, manganese porphyrins have demonstrated remarkable efficiency in the presence of suitable oxidants. Numerous studies have been conducted under both homogeneous and heterogeneous conditions, utilizing manganese porphyrins with various substitutions and reaction parameters. Most of these studies incorporated additives such as imidazoles, pyridine, and piperidine, among which imidazole proved particularly effective, often yielding complete conversion with exceptional selectivity. Furthermore, the catalytic reactivity is significantly influenced by factors such as solvent choice, temperature, pH, and reaction time. Herein, we present a multifaceted role of manganese porphyrins in tailoring the sulfoxidation reactions, by analysing the impact of different reaction conditions and ligand modifications. Furthermore, we aim to provide deeper insights into optimizing these catalytic systems while also unravelling their mechanistic aspects. Moreover, this review underscores the significance of structural tuning in manganese porphyrins to enhance catalytic efficiency.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134837"},"PeriodicalIF":2.2,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144721031","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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