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Journal of Heterocyclic Chemistry最新文献

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Recyclization of 3-substituted-6,8-dimethylchromones with some heterocyclic enamines: Spectroscopic, quantum calculations (HOMO–LUMO, MEP, NLO), biological evaluation, and ADME investigation 3-取代的-6,8-二甲基色酮与一些杂环烯胺的再环化：光谱、量子计算（HOMO-LUMO、MEP、NLO）、生物评估和 ADME 研究
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-24 DOI: 10.1002/jhet.4827
Al-Shimaa Badran, Magdy A. Ibrahim
{"title":"Recyclization of 3-substituted-6,8-dimethylchromones with some heterocyclic enamines: Spectroscopic, quantum calculations (HOMO–LUMO, MEP, NLO), biological evaluation, and ADME investigation","authors":"Al-Shimaa Badran,&nbsp;Magdy A. Ibrahim","doi":"10.1002/jhet.4827","DOIUrl":"10.1002/jhet.4827","url":null,"abstract":"<p>The chemical reactivity of some 6,8-dimethylchromones was studied toward certain heterocyclic enamines. Treatment of carboxaldehyde <b>1a</b> with the certain enamines proceeded via condensation with concomitant γ-pyrone ring opening. Reaction of carbonitrile <b>1b</b> with enamine derivatives proceeded through opening of γ-pyrone moiety associated with cycloaddition into the nitrile function. A novel angular chromenopyrazolopyridine and chromenopyridopyrimidines were efficiently synthesized from reacting carboxamide <b>1c</b> with the current enamines. Moreover, frontier molecular orbitals analysis, electronegativity, global hardness, global softness, ionization energy, and HOMO-LUMO energy gap were calculated by using DFT/B3LYP/6-311++G(d,p) level. Using the GIAO approach, the <sup>1</sup>H and <sup>13</sup>C NMR spectra were calculated and showed good agreement with the experimental values. Additionally, the nonlinear optical (NLO) properties of the prepared compounds were found higher than urea. MEP was utilized to ascertain reactive sites within the molecules. The produced compounds exhibited varying degrees of inhibitory effect when tested for their antimicrobial and anticancer properties. The evaluation of ADME (absorption, distribution, metabolism, and excretion) parameters indicated good drug-like properties of all the investigated compounds.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1224-1247"},"PeriodicalIF":2.0,"publicationDate":"2024-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141101494","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
A synthetic strategy for the preparation of alkoxy-functionalized bis-1,2,4-triazinyl-2,6-pyridines 制备烷氧基官能化双-1,2,4-三嗪基-2,6-吡啶的合成策略
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-23 DOI: 10.1002/jhet.4828
Mariah L. Tedder, Jesse D. Carrick
{"title":"A synthetic strategy for the preparation of alkoxy-functionalized bis-1,2,4-triazinyl-2,6-pyridines","authors":"Mariah L. Tedder,&nbsp;Jesse D. Carrick","doi":"10.1002/jhet.4828","DOIUrl":"10.1002/jhet.4828","url":null,"abstract":"<p>Heteroaryl-1,2,4-triazine complexants are commonly utilized in separation science for the selective chelation of minor An from Ln in simulated high-level waste. To facilitate access to relevant chemical entities for hypothesis-driven inquiry toward improved separations performance, a synthetic method to construct various alkoxy-complexant derivatives was required. In this work, a convergent synthetic strategy for the production of 3,3′- and 4,4′-tetraalkoxy-bis-1,2,4-triazinyl-2,6-pyridines from readily available starting materials via a dealkylation/alkylation/condensation approach is described. Synthetic method development, substrate scope, preliminary solubility, and hydrolytic stability data in various process-relevant diluents are reported herein.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1211-1223"},"PeriodicalIF":2.0,"publicationDate":"2024-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141103105","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
Simple and green synthesis of 3-acyl-pyrazolo[1,5-a]pyridines: [3+2] through cycloaddition of N-aminopyridines on enaminones 3-acyl-pyrazolo[1,5-a]pyridines 的简单绿色合成：通过 N-氨基吡啶与烯胺酮的环加成反应实现 [3+2］
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-22 DOI: 10.1002/jhet.4851
Sébastien Redon, Patrice Vanelle
{"title":"Simple and green synthesis of 3-acyl-pyrazolo[1,5-a]pyridines: [3+2] through cycloaddition of N-aminopyridines on enaminones","authors":"Sébastien Redon,&nbsp;Patrice Vanelle","doi":"10.1002/jhet.4851","DOIUrl":"10.1002/jhet.4851","url":null,"abstract":"<p><b>A practicable method is described for the synthesis of 3-acyl-pyrazolo[1,5-<i>a</i>]pyridines from <i>N</i>-aminopyridines and easily available enaminones <i>via</i> a [3+2] cycloaddition. The reactions proceed well with a broad scope, without using additive (base or oxidant).</b></p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1200-1205"},"PeriodicalIF":2.0,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.4851","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141107980","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
2-Vinylaniline in the synthesis of heterocycles: Recent advances 2 乙烯基苯胺在杂环合成中的应用：最新进展
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-21 DOI: 10.1002/jhet.4838
Fatemeh Doraghi, Hamed Navid, Somaye Karimian, Bagher Larijani, Mohammad Mahdavi
{"title":"2-Vinylaniline in the synthesis of heterocycles: Recent advances","authors":"Fatemeh Doraghi,&nbsp;Hamed Navid,&nbsp;Somaye Karimian,&nbsp;Bagher Larijani,&nbsp;Mohammad Mahdavi","doi":"10.1002/jhet.4838","DOIUrl":"10.1002/jhet.4838","url":null,"abstract":"<p>2-Vinylanilines are readily accessible substrates, which are undoubtedly one of the best candidates for the construction of diversely nitrogen-containing heterocyclic compounds. Owing to the amine and alkenyl groups in their structures, these frameworks offer a facile, direct, and selective synthetic method. This review describes various cyclization reactions involving 2-vinylanilines catalyzed by transition metals, or under metal-free conditions.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1180-1199"},"PeriodicalIF":2.0,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141118245","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
A review on pyrimidine-based derivatives: Synthesis and their biological application 嘧啶类衍生物综述：合成及其生物学应用
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-21 DOI: 10.1002/jhet.4837
Md. Wahidul Islam, Md. Monarul Islam, Rabeya Akter, Tayebur Rahman Limon, Erick S. Vasquez, Md. Aftab Ali Shaikh, Ahsan Habib
{"title":"A review on pyrimidine-based derivatives: Synthesis and their biological application","authors":"Md. Wahidul Islam,&nbsp;Md. Monarul Islam,&nbsp;Rabeya Akter,&nbsp;Tayebur Rahman Limon,&nbsp;Erick S. Vasquez,&nbsp;Md. Aftab Ali Shaikh,&nbsp;Ahsan Habib","doi":"10.1002/jhet.4837","DOIUrl":"10.1002/jhet.4837","url":null,"abstract":"<p>Pyrimidine-based derivatives have attracted a lot of interest in heterocyclic chemistry due to its versatile structure and diverse biological activities. This study provides a comprehensive overview of synthetic strategy of different pyrimidine ring and highlights their biological importance. In this article, we start off by going through the fundamental procedures for the synthesis of pyrimidine scaffolds, including both conventional and contemporary synthetic techniques. These works cover a range of therapeutic domains, such as effects that are anticancer, antibacterial, antiviral, anti-inflammatory, antioxidant, antimalarial, and so on. Moreover, we have summarized with a discussion of future prospects and challenges in the field of pyrimidine heterocyclic chemistry. This thorough review is a significant resource for researchers in medicinal chemistry and related fields since it offers insightful information about the synthetic methods and biological applications of pyrimidine-based derivatives.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1159-1179"},"PeriodicalIF":2.0,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141117587","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
Convenient synthesis and antibacterial evaluation of new bipyrazolyl and pyrazolopyridazine derivatives utilizing 4-acetyl-5-methyl-N-phenyl-1-(p-tolyl)-1H-pyrazole-3-carboxamide as a versatile precursor 以 4-乙酰基-5-甲基-N-苯基-1-(对甲苯基)-1H-吡唑-3-甲酰胺为多功能前体，方便合成新的双吡唑和吡唑并哒嗪衍生物并进行抗菌评估
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-18 DOI: 10.1002/jhet.4833
Monica G. Kamel, Mirna T. Helmy, Fatma M. Saleh, Hamdi M. Hassaneen, Omar A. Shehata, Yara N. Laboud
{"title":"Convenient synthesis and antibacterial evaluation of new bipyrazolyl and pyrazolopyridazine derivatives utilizing 4-acetyl-5-methyl-N-phenyl-1-(p-tolyl)-1H-pyrazole-3-carboxamide as a versatile precursor","authors":"Monica G. Kamel,&nbsp;Mirna T. Helmy,&nbsp;Fatma M. Saleh,&nbsp;Hamdi M. Hassaneen,&nbsp;Omar A. Shehata,&nbsp;Yara N. Laboud","doi":"10.1002/jhet.4833","DOIUrl":"10.1002/jhet.4833","url":null,"abstract":"<p>4-(3-(Dimethylamino)acryloyl)-5-methyl-<i>N</i>-phenyl-1-(<i>p</i>-tolyl)-1<i>H</i>-pyrazole-3-carboxamide was prepared <i>via</i> refluxing of 4-acetyl-5-methyl-<i>N</i>-phenyl-1-(<i>p</i>-tolyl)-1<i>H</i>-pyrazole-3-carboxamide with dimethylformamide dimethyl acetal. The target bipyrazoles were obtained from regioselective reaction of the latter enaminone with different hydrazonoyl halides at reflux in chloroform in the presence of trimethylamine. The regioselectivity was confirmed chemically upon refluxing with hydrazine hydrate in ethanol. The structures of the newly synthesized compounds were established on the basis of their elemental analyses and spectral data. The specified compounds were tested for antibacterial activity against gram-negative bacteria (<i>Escherichia coli</i>) and (<i>Pseudomonas aeruginosa</i>) and a gram-positive bacteria (<i>Bacillus subtilis</i>) and (<i>Staphylococcus aureus</i>) using disk diffusion method. Antibacterial studies revealed that compounds <b>8a</b>, <b>10b</b>, <b>10c, 11d,</b> and <b>14b</b> showed weak to moderate activity against the tested bacteria compared to ampicillin.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1150-1158"},"PeriodicalIF":2.0,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141060903","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
Simple and efficient synthesis of pyrrolo[3,2-f]quinoxaline derivatives via three-component reaction 通过三组分反应简单高效地合成吡咯并[3,2-f]喹喔啉衍生物
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-18 DOI: 10.1002/jhet.4822
Dan-Dan Wan, Yu-heng Qian, Jia-Yan Liu, Dong-Sheng Chen
{"title":"Simple and efficient synthesis of pyrrolo[3,2-f]quinoxaline derivatives via three-component reaction","authors":"Dan-Dan Wan,&nbsp;Yu-heng Qian,&nbsp;Jia-Yan Liu,&nbsp;Dong-Sheng Chen","doi":"10.1002/jhet.4822","DOIUrl":"10.1002/jhet.4822","url":null,"abstract":"<p>A series of pyrrolo[3,2-<i>f</i>]quinoxaline derivatives have been obtained by a three-component domino reaction of quinoxalin-6-amine, arylglyoxal monohydrates, and cyclic 1,3-dicarbonyl compounds in ethanol medium at 80°C catalyzed by acetic acid. The notable features of this synthesis are excellent regioselectivity, operational simplicity, relatively mild reaction conditions, and good yields.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1141-1149"},"PeriodicalIF":2.0,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141060902","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
Design, synthesis, biological evolution and in silico studies of a novel 1,2,3,4-tetrazole fused with 1,3,4-thiadiazole-2-amine derivatives 新型 1,2,3,4-四氮唑与 1,3,4-噻二唑-2-胺衍生物的设计、合成、生物进化和硅学研究
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-17 DOI: 10.1002/jhet.4831
Muthirevula Rajeswari, Begari Nagaraju, Shaik Yasmintaj, Pamerla Muralidhar, Chunduri Venkata Rao, Prashantha Karunakar, Suresh Maddila
{"title":"Design, synthesis, biological evolution and in silico studies of a novel 1,2,3,4-tetrazole fused with 1,3,4-thiadiazole-2-amine derivatives","authors":"Muthirevula Rajeswari,&nbsp;Begari Nagaraju,&nbsp;Shaik Yasmintaj,&nbsp;Pamerla Muralidhar,&nbsp;Chunduri Venkata Rao,&nbsp;Prashantha Karunakar,&nbsp;Suresh Maddila","doi":"10.1002/jhet.4831","DOIUrl":"10.1002/jhet.4831","url":null,"abstract":"<p>A new series of tetrazole fused with 1,3,4-thiadiazole-2-amine (<b>4a–j</b>) moiety have been synthesized. A thorough characterization of each compound was carried out using mass spectrum data, FT-IR, <sup>1</sup>H, and <sup>13</sup>C NMR studies. The antibacterial effectiveness of these prepared substances was assessed in vitro against Gram-(−) strains of <i>P. aeruginosa</i> and <i>E. coli</i>, as well as Gram-(+) strains of <i>B. subtilis</i> and <i>S. aureus</i>. Molecules <b>4f</b> and <b>4h</b> showed exceptional effectiveness against both types of strains when compared to the reference antibiotic Streptomycin. Moreover the evolution of the molecular docking (<i>in silico</i>) studies also helpful for all the synthesized compounds and reference amoxicillin. The investigation included a look at protein stability, APO-protein dynamics, and interactions. Using Molecular Dynamics (MD) simulations with Desmond Maestro version 11.3 for this inquiry, a potential lead molecule was found.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1116-1124"},"PeriodicalIF":2.0,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141060869","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
New oxadiazol-5-ones derivatives and their performance as angiotensin-converting enzyme (ACE) inhibitors 新型噁二唑-5-酮衍生物及其作为血管紧张素转换酶（ACE）抑制剂的性能
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-17 DOI: 10.1002/jhet.4835
Larissa Fernanda Lima Ferreira, Ilária Martina Silva Lins, Sidney Gustavo Diniz Feitosa, Jivaldo Gonçalves Ferreira, Larissa Gonçalves Maciel, Alice Valença Araújo, Janaína Versiani dos Anjos
{"title":"New oxadiazol-5-ones derivatives and their performance as angiotensin-converting enzyme (ACE) inhibitors","authors":"Larissa Fernanda Lima Ferreira,&nbsp;Ilária Martina Silva Lins,&nbsp;Sidney Gustavo Diniz Feitosa,&nbsp;Jivaldo Gonçalves Ferreira,&nbsp;Larissa Gonçalves Maciel,&nbsp;Alice Valença Araújo,&nbsp;Janaína Versiani dos Anjos","doi":"10.1002/jhet.4835","DOIUrl":"10.1002/jhet.4835","url":null,"abstract":"<p>Angiotensin-converting enzyme inhibitors are widely used in treating arterial hypertension, acting on the renin-angiotensin-aldosterone system and controlling blood pressure. We present a novel, greener, and faster methodology to assess the 1,2,4-oxadiazol-5-one ring and perform molecular modifications to obtain angiotensin-converting enzyme (ACE) inhibitors using this heterocyclic core. Molecular docking simulations indicate that the tested compounds exhibited an affinity for the ACE binding site, with scores comparable to the commercial inhibitor lisinopril. However, in vitro assays revealed that the compounds were ineffective in inhibiting ACE activity. The lack of inhibition may be related to the compounds' more apolar nature. These results emphasize the importance of integrating computational and experimental approaches in developing new drugs, providing valuable insights for planning future studies to optimize the activity of synthesized compounds.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1125-1140"},"PeriodicalIF":2.0,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141060912","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
Synthesis of various 1-alkylbenzimidazole derivatives directly from 2-alkylaminonitroarenes via a two-step, one-pot procedure 通过两步一步法直接从 2-烷基氨基硝基苯烯合成各种 1-烷基苯并咪唑衍生物
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-14 DOI: 10.1002/jhet.4830
Magdalena Walewska-Królikiewicz, Bogdan Wilk, Andrzej Kwast, Zbigniew Wróbel
{"title":"Synthesis of various 1-alkylbenzimidazole derivatives directly from 2-alkylaminonitroarenes via a two-step, one-pot procedure","authors":"Magdalena Walewska-Królikiewicz,&nbsp;Bogdan Wilk,&nbsp;Andrzej Kwast,&nbsp;Zbigniew Wróbel","doi":"10.1002/jhet.4830","DOIUrl":"10.1002/jhet.4830","url":null,"abstract":"<p><i>N</i>-Alkyl-2-nitroanilines deoxygenated with tributylphosphine form intermediate 2-(alkylamino)aryliminophosphoranes, which were subjected, without isolation, to various cyclocondensation reactions with CS<sub>2</sub>, CO<sub>2</sub>, alkyl isocyanates, acyl chlorides, anhydrides, or esters. A simple, convenient, one-pot procedure provided derivatives of unsymmetrically substituted 1-alkylbenzimidazoles functionalized at C2 in good to excellent yields. The method does not require the use of metals, sensitive catalysts, or pressure.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1101-1115"},"PeriodicalIF":2.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932096","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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