R. Balo, A. Jiménez, David Reza, R. Estévez, J. Estévez
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain; email1 (R.B.); email2 (A.J.); email3 (D.R.); email4 (R.J.E.) * Correspondence: juancarlos.estevez@usc.es; Tel.: +34-881-815-730 † Presented at the 25th International Electronic Conference on Synthetic Organic Chemistry, 15–30 November 2021; Available online: https://ecsoc-25.sciforum.net/.
{"title":"Peptides Incorporating 3,4-Dihydroxyprolines: Synthesis and Structural Study","authors":"R. Balo, A. Jiménez, David Reza, R. Estévez, J. Estévez","doi":"10.3390/ecsoc-25-11683","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11683","url":null,"abstract":"Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain; email1 (R.B.); email2 (A.J.); email3 (D.R.); email4 (R.J.E.) * Correspondence: juancarlos.estevez@usc.es; Tel.: +34-881-815-730 † Presented at the 25th International Electronic Conference on Synthetic Organic Chemistry, 15–30 November 2021; Available online: https://ecsoc-25.sciforum.net/.","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90275857","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Organic–Inorganic Hybrid Sol–Gel Material Loaded with an Heterocyclic Aldehyde with Potential Application for Cu(II) Detection","authors":"R. P. Sousa, S. Costa, R. B. Figueira, M. Raposo","doi":"10.3390/ecsoc-25-11682","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11682","url":null,"abstract":"","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87618213","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: 2-Hydroxy- N -phenylnaphthalene-1-carboxamide, three fluoro monosubstituted and five fluoro disubstituted 2-hydroxynaphthalene-1-carboxanilides were prepared by microwave-assisted synthesis and characterized. All the compounds were evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach ( Spinacia oleracea L.) chloroplasts. The PET inhibitory activity of the discussed compounds proved to be in a wide range, from inactive N -(2,6-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC 50 = 904 µ M to N -(2,5-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC 50 of 44.2 µ M, which was the most potent isomer of the series of evaluated compounds. Based on previous studies, it can be assumed that the mechanism of PET inhibition of these compounds is the inhibition of photosystem II in the thylakoid membrane.
采用微波辅助合成方法制备了2-羟基- N -苯基萘-1-羧酰胺、3个氟单取代和5个氟二取代的2-羟基萘-1-羧苯胺并对其进行了表征。所有化合物对菠菜叶绿体光合电子传递(PET)的抑制能力进行了评价。所讨论的化合物的PET抑制活性范围很广，从无活性的N -(2,6-二氟苯基)-2-羟基萘-1-羧酰胺(IC 50 = 904µM)到N -(2,5-二氟苯基)-2-羟基萘-1-羧酰胺(IC 50为44.2µM)，是该系列化合物中最有效的异构体。根据以往的研究，可以认为PET抑制这些化合物的机制是抑制类囊体膜中的光系统II。
{"title":"Photosynthesis-Inhibiting Activity of Fluorinated 2-Hydroxynaphthalene-1-carboxanilides","authors":"T. Goněc, M. Oravec, J. Jampílek","doi":"10.3390/ecsoc-25-11652","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11652","url":null,"abstract":": 2-Hydroxy- N -phenylnaphthalene-1-carboxamide, three fluoro monosubstituted and five fluoro disubstituted 2-hydroxynaphthalene-1-carboxanilides were prepared by microwave-assisted synthesis and characterized. All the compounds were evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach ( Spinacia oleracea L.) chloroplasts. The PET inhibitory activity of the discussed compounds proved to be in a wide range, from inactive N -(2,6-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC 50 = 904 µ M to N -(2,5-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC 50 of 44.2 µ M, which was the most potent isomer of the series of evaluated compounds. Based on previous studies, it can be assumed that the mechanism of PET inhibition of these compounds is the inhibition of photosystem II in the thylakoid membrane.","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86283205","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: The Taguchi method was used to evaluate effect of process parameters in microencapsulation process of beeswax with resorcinol modified phenol-formaldehyde shell. Orthogonal array of 5 3 was constructed to study effect of process parameters core to shell ratio, surfactant concentration and agitation speed on control parameter core content. The amount of core content is directly proportional to heat storing capacity of microcapsules. Surfactant concentration, core to shell ratio, and agitation speed were optimized at 3%, 1:1, and 800 rpm, respectively. The microcapsules synthesized with optimized process parameters values possessed spherical morphology and heat transition enthalpy 148.93 J/g within temperature range 35 – 62 °C.
{"title":"Synthesis of Microcapsules with Beeswax Core and Phenol-Formaldehyde Shell by Taguchi Method","authors":"Tejashree Amberkar, P. Mahanwar","doi":"10.3390/ecsoc-25-11671","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11671","url":null,"abstract":": The Taguchi method was used to evaluate effect of process parameters in microencapsulation process of beeswax with resorcinol modified phenol-formaldehyde shell. Orthogonal array of 5 3 was constructed to study effect of process parameters core to shell ratio, surfactant concentration and agitation speed on control parameter core content. The amount of core content is directly proportional to heat storing capacity of microcapsules. Surfactant concentration, core to shell ratio, and agitation speed were optimized at 3%, 1:1, and 800 rpm, respectively. The microcapsules synthesized with optimized process parameters values possessed spherical morphology and heat transition enthalpy 148.93 J/g within temperature range 35 – 62 °C.","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75136652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
F. J. Miquel-Leal, Natalia González-Zapata, O. J. Jimenez-Jarava, Yaneth Brand, L. Betancur-Galvis, M. Marín, Miguel A. González-Cardenete
: Virus-induced diseases are very common in our society, and we continuously need new treatments for these challenging infections. We discovered by serendipity some years ago that the molecule 18-(Phthalimide-2-yl)ferruginol, an analogue of the natural diterpenoid (+)-ferruginol, a pharmacologically active molecule, was able to inhibit the spread of dengue virus type-2 (DENV-2) and human herpes virus 1 and 2 (HHV-1 and HHV-2). During the development and further study of the above-mentioned analogue, we required the scaling-up of the semisynthesis of the target molecule. The synthesis was already reported by Waldvogel and co-workers in 2007, starting from the commercially available ca. 60% (+)-dehydroabietylamine. In this communication, we describe the several issues that we faced and propose an optimized experimental procedure in order to obtain this broad-spectrum antiviral, which we found is even active against several strains of Zika virus. which had 1 H and 13 C NMR and specific optical rotation ([ α ] 23D —31.4 (c 0.7, DCM) data in agreement with reported [7]. Anal. calcd. for C 28 H 33 NO 3 : C, 77.9; H, 7.7; N, 3.2. Found: C, 77.6; H, 7.8;
{"title":"Development and Optimization of the Multi-Gram Synthesis of the Antiviral 18-(Phthalimide-2-yl)ferruginol","authors":"F. J. Miquel-Leal, Natalia González-Zapata, O. J. Jimenez-Jarava, Yaneth Brand, L. Betancur-Galvis, M. Marín, Miguel A. González-Cardenete","doi":"10.3390/ecsoc-25-11667","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11667","url":null,"abstract":": Virus-induced diseases are very common in our society, and we continuously need new treatments for these challenging infections. We discovered by serendipity some years ago that the molecule 18-(Phthalimide-2-yl)ferruginol, an analogue of the natural diterpenoid (+)-ferruginol, a pharmacologically active molecule, was able to inhibit the spread of dengue virus type-2 (DENV-2) and human herpes virus 1 and 2 (HHV-1 and HHV-2). During the development and further study of the above-mentioned analogue, we required the scaling-up of the semisynthesis of the target molecule. The synthesis was already reported by Waldvogel and co-workers in 2007, starting from the commercially available ca. 60% (+)-dehydroabietylamine. In this communication, we describe the several issues that we faced and propose an optimized experimental procedure in order to obtain this broad-spectrum antiviral, which we found is even active against several strains of Zika virus. which had 1 H and 13 C NMR and specific optical rotation ([ α ] 23D —31.4 (c 0.7, DCM) data in agreement with reported [7]. Anal. calcd. for C 28 H 33 NO 3 : C, 77.9; H, 7.7; N, 3.2. Found: C, 77.6; H, 7.8;","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85664189","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
L. Jadhav, R. Patil, Nikhil Borane, S. Mishra, G. Yadav, D. Patil, V. Patil
: A novel synthetic method has been developed by utilizing the chemical reactivity of functionalized graphene and CNT with a covalent combination of chemically diverse GO/FCNT and toluene diisocyanate. Thereby yield a synergistic polymer nanocomposite. Comprehensive composite material has simultaneous covalent as well as π - π interactions confirms sp2-hybridized frameworks of graphene oxide and MWCNTs by Raman absorption spectra at 1345 and 1590 cm −1 of D and G band respectively. Toluene diisocyanate and GO/FCNT inspired polymeric formulation obtained by the classical curing reaction initiated by ultrasound sonication. This method allowed 50 wt.% doping of GO/FCNT without segregation ensures good adhesion to the law steel surface. Large surface area and morphological character of GO and FCNT by SEM and TEM ensure stable and dispersed integrated molecules. It has advantages over the high-temperature hazardous curing reaction overcomes the problem of graphene exfoliation and does not allow CNT slipping within the bundle to falls apart at higher concentration.
{"title":"A Novel Synthetic Approach of Functionalised GO and CNT to Nanocomposite Containing Active Nanostructured Fillers for Classical Isocyanate Curing","authors":"L. Jadhav, R. Patil, Nikhil Borane, S. Mishra, G. Yadav, D. Patil, V. Patil","doi":"10.3390/ecsoc-25-11679","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11679","url":null,"abstract":": A novel synthetic method has been developed by utilizing the chemical reactivity of functionalized graphene and CNT with a covalent combination of chemically diverse GO/FCNT and toluene diisocyanate. Thereby yield a synergistic polymer nanocomposite. Comprehensive composite material has simultaneous covalent as well as π - π interactions confirms sp2-hybridized frameworks of graphene oxide and MWCNTs by Raman absorption spectra at 1345 and 1590 cm −1 of D and G band respectively. Toluene diisocyanate and GO/FCNT inspired polymeric formulation obtained by the classical curing reaction initiated by ultrasound sonication. This method allowed 50 wt.% doping of GO/FCNT without segregation ensures good adhesion to the law steel surface. Large surface area and morphological character of GO and FCNT by SEM and TEM ensure stable and dispersed integrated molecules. It has advantages over the high-temperature hazardous curing reaction overcomes the problem of graphene exfoliation and does not allow CNT slipping within the bundle to falls apart at higher concentration.","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79793155","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jorge M. S. Faria, P. Barbosa, C. Moiteiro, M. Mota, M. Inácio
{"title":"Profiling the Nematicidal Activity of Linear and Cyclic Compounds on the Pinewood Nematode","authors":"Jorge M. S. Faria, P. Barbosa, C. Moiteiro, M. Mota, M. Inácio","doi":"10.3390/ecsoc-25-11641","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11641","url":null,"abstract":"","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74650748","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Functionally substituted bicyclo[4.2.1]nona-2,4,7-trienes were synthesized for the first time on the basis of the reaction of [6 π + 2 π ] cycloaddition of hexyn-1 and 4-pentynenitrile to 1-benzoylcycloheptatriene under the action of the three-component catalytic system Co(acac) 2 (dppe)/ Zn/ZnI 2 .
{"title":"Synthesis of New Functionally Substituted Bicyclo[4.2.1]nona-2,4,7-trienes by Co(I)-Catalyzed [6π + 2π] Cycloaddition of 1-Benzoylcycloheptatriene","authors":"G. N. Kadikova, L. Dzhemileva, U. Dzhemilev","doi":"10.3390/ecsoc-25-11631","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11631","url":null,"abstract":": Functionally substituted bicyclo[4.2.1]nona-2,4,7-trienes were synthesized for the first time on the basis of the reaction of [6 π + 2 π ] cycloaddition of hexyn-1 and 4-pentynenitrile to 1-benzoylcycloheptatriene under the action of the three-component catalytic system Co(acac) 2 (dppe)/ Zn/ZnI 2 .","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78263556","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Currently, mitochondria are considered as an attractive universal target in the development of new anticancer drugs. These organelles are essential in energy production, regulation of cell death pathways, generation of reactive oxygen species, as well as maintenance of calcium ho-meostasis. Various approaches are being developed to deliver biologically active compounds into the mitochondria of tumour cells, including conjugation of cytotoxic substances with mitochondria-targeted lipophilic cations. Among the currently known low molecular weight lipophilic cationic molecules, (E)-4(1H-indol-3-ylvinyl)-N-methylpyridinium iodide ( F16 ) is of great interest. This mi-tochondria-toxic cationic compound with luminescent properties is selectively accumulated in mitochondria and can selectively trigger apoptosis and necrosis of tumour cells, making it an attractive targeted agent for theranostic use. Meanwhile, betulinic acid, an available natural pentacyclic triterpenoid, has been considered as a promising scaffold for development of new anticancer agents in recent years. The antitumour effect of this natural product arises from affecting the mitochondria of tumour cells through formation of reactive oxygen species. The present article details an efficient synthesis of a novel multifunctional hybrid agent in which a cytotoxic triterpenoid, betulinic acid, is carbon-carbon bonded to the cationic F16 fragment at the C-2 position of ring A through a phenylethynyl spacer. The starting substrates in the synthesis were C-2 propynyl derivative of betulinic acid and N-aryl-substituted 4-(1H-indol-3-ylvinyl)-pyridine. The derivative of betulinic acid with a terminal acetylenic group was prepared by the reaction of C-alkylation with propargyl bromide of potassium enoxytriethylborate generated from betulonic acid. To obtain the N-aryl-substituted an-alogue of F16 , CuI-catalyzed Ullmann-Goldberg reaction was applied. The synthesis of the target conjugate was successfully completed by the cross-coupling of the terpene and heterocyclic compo-nents according to Sonogashira in the presence of CuI/Pd(PPh 3 ) 2 catalyst.
目前，线粒体被认为是开发新的抗癌药物的一个有吸引力的通用靶点。这些细胞器在能量产生、细胞死亡途径的调节、活性氧的产生以及钙稳态的维持中都是必不可少的。目前正在开发各种方法来将生物活性化合物输送到肿瘤细胞的线粒体中，包括将细胞毒性物质与靶向线粒体的亲脂性阳离子结合。在目前已知的低分子量亲脂性阳离子分子中，(E)-4(1h -吲哚-3-基乙烯基)- n -甲基碘化吡啶(F16)引起了极大的兴趣。这种具有发光特性的中线粒体毒性阳离子化合物选择性地积聚在线粒体中，可以选择性地引发肿瘤细胞的凋亡和坏死，使其成为一种有吸引力的靶向治疗药物。同时，白桦酸作为一种天然的五环三萜化合物，近年来被认为是一种很有前途的新型抗癌药物支架。这种天然产物的抗肿瘤作用是通过形成活性氧来影响肿瘤细胞的线粒体。本文详细介绍了一种新型多功能杂化剂的高效合成，其中细胞毒性三萜白桦酸通过苯乙基间隔物与a环C-2位置的阳离子F16片段碳碳结合。合成的起始底物为桦木酸的C-2丙基衍生物和n -芳基取代的4-(1h -吲哚-3-基乙烯基)吡啶。以桦木酸为原料，以乙氧三乙基硼酸钾为原料，与丙炔溴化反应制备了末端为乙基的桦木酸衍生物。采用cui催化Ullmann-Goldberg反应得到F16的n-芳基取代偶联物。在CuI/Pd(PPh 3) 2催化剂的作用下，萜类化合物与杂环化合物按照Sonogashira的要求进行交叉偶联，成功合成了目标缀合物。
{"title":"Effective Synthesis of a Novel Betulinic Acid Conjugate with Mitochondria-Targeting Cation F16","authors":"D. Nedopekina, E. Davletshin, A. Spivak","doi":"10.3390/ecsoc-25-11638","DOIUrl":"https://doi.org/10.3390/ecsoc-25-11638","url":null,"abstract":": Currently, mitochondria are considered as an attractive universal target in the development of new anticancer drugs. These organelles are essential in energy production, regulation of cell death pathways, generation of reactive oxygen species, as well as maintenance of calcium ho-meostasis. Various approaches are being developed to deliver biologically active compounds into the mitochondria of tumour cells, including conjugation of cytotoxic substances with mitochondria-targeted lipophilic cations. Among the currently known low molecular weight lipophilic cationic molecules, (E)-4(1H-indol-3-ylvinyl)-N-methylpyridinium iodide ( F16 ) is of great interest. This mi-tochondria-toxic cationic compound with luminescent properties is selectively accumulated in mitochondria and can selectively trigger apoptosis and necrosis of tumour cells, making it an attractive targeted agent for theranostic use. Meanwhile, betulinic acid, an available natural pentacyclic triterpenoid, has been considered as a promising scaffold for development of new anticancer agents in recent years. The antitumour effect of this natural product arises from affecting the mitochondria of tumour cells through formation of reactive oxygen species. The present article details an efficient synthesis of a novel multifunctional hybrid agent in which a cytotoxic triterpenoid, betulinic acid, is carbon-carbon bonded to the cationic F16 fragment at the C-2 position of ring A through a phenylethynyl spacer. The starting substrates in the synthesis were C-2 propynyl derivative of betulinic acid and N-aryl-substituted 4-(1H-indol-3-ylvinyl)-pyridine. The derivative of betulinic acid with a terminal acetylenic group was prepared by the reaction of C-alkylation with propargyl bromide of potassium enoxytriethylborate generated from betulonic acid. To obtain the N-aryl-substituted an-alogue of F16 , CuI-catalyzed Ullmann-Goldberg reaction was applied. The synthesis of the target conjugate was successfully completed by the cross-coupling of the terpene and heterocyclic compo-nents according to Sonogashira in the presence of CuI/Pd(PPh 3 ) 2 catalyst.","PeriodicalId":11441,"journal":{"name":"ECSOC-25","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73652129","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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