Journal of Organic and Pharmaceutical Chemistry最新文献

{"title":"N-Silylimine of Trifluoropyruvate in the Asymmetric Synthesis of Trifluoroalanine Derivatives","authors":"A. S. Cherednichenko, Y. Rassukana","doi":"10.24959/ophcj.23.284819","DOIUrl":"https://doi.org/10.24959/ophcj.23.284819","url":null,"abstract":"Aim. To develop a preparative method for the synthesis of N-trimethylsilylimine of trifluoropyruvate, and study its interaction with acetone under organocatalytic conditions.Results and discussion. A simple preparative approach to the first representative of N-silylimines of trifluoropyruvate was developed based on the interaction of triphenylphosphinimide and trifluoropyruvic acid methyl ester by the aza-Wittig reaction. It was found that the addition of acetone to N-silylimine occurred in the presence of L- or D-proline and led to the formation of enantiomerically enriched α-amino-γ-oxocarboxylates. The hydrolysis of the ester function resulted in (R)-α-trifluoromethyl aminocarboxylic acid, and the cyclocondensation with isocyanates or 2,5-dimethoxytetrahydrofuran yielded nitrogen-containing heterocycles containing pyrimidine or pyrrolizine nuclei.Experimental part. The synthetic procedures for the N-silylimine of trifluoropyruvate and its reaction with acetone are provided, along with the transformations of obtained α-amino-γ-oxocarboxylates (hydrolysis, cyclocondensations with isocyanates and 2,5-dimethoxytetrahydrofuran). The structures of the compounds synthesized were proven by 1H, 13C, 19F NMR spectroscopy methods, as well as by the elemental analysis.Conclusions. A convenient method for the synthesis of N-silylimine of trifluoropyruvate has been developed. Using the example of the Mannich reaction with acetone, it has been demonstrated that N-silylimine of trifluoropyruvate is a convenient substrate for the synthesis of optically active 3,3,3-trifluoroalanine derivatives.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"17 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87662936","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":"Assessment of the Commercially Available Chemical Space for Using in the 19F NMR FAXS Method: a Enamine Ltd. Case","authors":"Oleksandr V. Oksiuta, Yaroslav I. Filatov","doi":"10.24959/ophcj.23.281281","DOIUrl":"https://doi.org/10.24959/ophcj.23.281281","url":null,"abstract":"Aim. To analyze commercially available fluorine containing compounds for the possibility of their use in the 19F NMR FAXS method.Materials and methods. The selection of fluorine-containing fragments for the study was performed using 3.9 million instock screening compounds and 248,000 in-stock building-blocks from Enamine Ltd library. The selection and classification of the compounds was carried out using the DataWarrior and KNIME software. The Fluorinated Fragments library of Enamine Ltd. containing 6377 compounds, was also analyzed. To analyze the abovementioned sets of substances, the multistep workflows specially designed were used.Results and discussion. As a result of applying the workflow developed to the compound sets (both screening compounds and building blocks), 13 800 compounds were selected and further classified according to the presence of one out of 12 fluorine-containing groups. The Fluorinated Fragments library was also subjected to a similar workflow. For the latter, 8 out of 12 fluorine-containing groups were identified. Additionally, experimental 19F NMR chemical shift values for Fluorinated Fragments library compounds spectra were analyzed. It has been found that some structural classes have areas of chemical shifts intersection. On the other hand, the ranges from –40 to –60 ppm and beyond –160 ppm are free from any group of compounds from the library analyzed.Conclusions. The analysis has shown that commercially available fluorine-containing fragments do not satisfy the needs of the 19F NMR FAXS method, and further expansion of the chemical space of fluorine-containing compounds by increasing their diversity is required.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79777622","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":"The Synthesis and Acid-base Properties of α-(Fluoromethyl)- and α-(Difluoromethyl)-substituted Cyclobutane Building Blocks","authors":"Oleksandr Demchuk, O. Grygorenko","doi":"10.24959/ophcj.23.274017","DOIUrl":"https://doi.org/10.24959/ophcj.23.274017","url":null,"abstract":"Aim. To synthesize cyclobutane-derived amines and carboxylic acids bearing CH2F or CHF2 groups in the α position; to determine the regularities of the effect of fluoroalkyl substituents on the acid-base properties of the title compounds.Results and discussion. Synthetic approaches to 1-(fluoromethyl)- and 1-(difluoromethyl)cyclobutanamines, 1-(fluoromethyl)- and 1-(difluoromethyl)cyclobutanecarboxylic acids have been developed. It has been found that the pKa (pKa(H)) values measured for the title compounds, as well as for their non-substituted and CF3-substituted analogues, are consistent with the electron-withdrawing effect of the corresponding fluoroalkyl substituents.Experimental part. The synthesis of the title compounds commenced from the known ethyl 1-(hydroxymethyl)cyclobutanecarboxylate or the product of its Swern oxidation (the corresponding aldehyde) and included fluorination, alkaline ester hydrolysis (for carboxylic acids), and modified Curtius rearrangement (for amines). The pKa value was determined from the pre-equivalence point part of the titration curve using the standard acid-base titration.Conclusions. A newly developed synthetic approach to 1-(fluoromethyl)- and 1-(difluoromethyl)cyclobutanamines, 1-(fluoromethyl)- and 1-(difluoromethyl)cyclobutanecarboxylic acids allows to obtain the title compounds in multigram quantities (up to 97 g). With a single exception, the acid-base properties of these products, as well as their parent non-substituted and CF3-substituted analogues, change in a monotonous manner in accordance with inductive electronic effect of the fluorine atom(s).","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"86 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83219087","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":"The Quantitative Determination of Oxacillin Using Kinetiс-Spectrophotometric and Redox Titration Methods","authors":"S. Karpova, M. M. Ivashura, A. O. Koval, Iu. S. Kolisnyk","doi":"10.24959/ophcj.23.273654","DOIUrl":"https://doi.org/10.24959/ophcj.23.273654","url":null,"abstract":"The search for new analytical reactions and finding out the optimal conditions for their course, which can be used as the basis for quantitative analytical determinations of penicillins, is a very urgent task.Aim. To develop methods for the quantitative determination of Oxacillin.Materials and methods. The study object was Oxacillin sodium salt powder in vials for preparing a solution for injections(0.5 g). Peroxomonosulfate acid as triple potassium salt 2КНSO5∙КНSO4∙K2SO4 (Oxone®) of “extra pure” grade was used as an oxidant. The methods of kinetic spectriphotometry and redox titration were used.Results and discussion. A simple procedure for the quantitative determination of the Oxacillin pure substance by the kinetic spectrophotometry and redox titration methods using potassium hydrogen peroxomonosulfate (KHSO5) has been developed. The results of the drug analysis obtained by newly developed and current methods are in good agreement with each other; δ (correctness) = (0.45 – 0.86) %.Conclusions. Using the methods of kinetic spectrophotometric and redox titration, two independent procedures for thequantitative determination of oxacillin in the substance and the drug product have been developed using potassium hydrogen peroxomonosulfate as an analytical reagent (KHSO5). A relative standard deviation RSD = (1.24 – 2.17) %.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"101 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77615532","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":"The Synthesis of 1-Alkyl-3-polyfluoroalkyl- 1,3-dihydrobenzimidazole-2-selenones as Potential Plant Growth Regulators","authors":"K. I. Petko, V.Sh. Petrenko","doi":"10.24959/ophcj.23.278660","DOIUrl":"https://doi.org/10.24959/ophcj.23.278660","url":null,"abstract":"Aim. To synthesize new 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones and study their biological activity as potential plant growth regulators.Results and discussion. 1-Alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones were obtained from the corresponding 1-alkyl-3-polyfluoroalkylbenzimidazolium iodides by the action of elemental selenium in the presence of a base. The preliminary biological tests for the growth-regulating activity of the compounds obtained were conducted.Experimental part. The structure of the compounds synthesized was proven by 1H and 19F NMR spectroscopy methods, as well as by the elemental analysis. The biological studies were done on model plants of winter wheat of the “bezosta” variety.Conclusions. A convenient method for obtaining 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-benzimidazole-2-selenones has been developed. Biological studies have shown that the compounds synthesized have a diverse effect on the plant growth.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"39 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81705382","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":"Standardization Parameters of Alfredia nivea KAR.&KIR Herb","authors":"Almat G. Rustemkulov, T. Gontova, B. Makhatova, Aisana E. Rustemkulova, U. Datkhayev, O. Koshovyi","doi":"10.24959/ophcj.23.276004","DOIUrl":"https://doi.org/10.24959/ophcj.23.276004","url":null,"abstract":"The Kazakhstan flora is rich in promising poorly-studied plants, which are traditionally used in folk medicine, but their introduction into medical practice requires additional in-depth research using modern scientific methods. Alfredia nivea KAR&KIR of the Asteraceae family, which is used in folk medicine as a neurotropic agent, is an interesting object for introduction into official medical and pharmaceutical practice.Aim. To create new medicines based on Alfredia nivea herb, it is necessary to develop methods for quality control of this raw material, therefore, the aim of the research was to determine the parameters for standardization of the Alfredia nivea KAR & KIR. herb.Materials and methods. The study objects were samples of the A. nivea herb collected in Kungei Alatau, 4.3 km southeast of the Karabulak village, Eastern Karabulak canyon, Almaty Region, Kazakhstan. The macroscopic and microscopic studies of the A. nivea herb were performed according to the methodology of the European pharmacopeia (EuPh) 2.8.23 “Microscopic examination of the medicinal plant raw material”. The macroscopic studies were performed using a magnifying glass and a MBS-9 binocular microscope, the microscopic studies were done using MS Microscopes 10 (oculars X5, X10, X15, lenses x10,x40), Micromed XS-4130 (oculars WF15X, lenses x40/0.65, x10/0.25) with a microphotonozzle (China). Identification of the main substances was carried out by the TLC method, testing and the quantitative determination of the flavonoid content were performed according to the EuPh methods.Results and discussion. Morphological and anatomical features of the A. nivea herb have been determined; on their basis Identifications A and B have been proposed; TLC Identification C of the main BAS of the raw material has been developed; indicators of purity tests have been determined. It has been proposed to carry out the quantitative determination by the content of flavonoids.Conclusions. The parameters of the A. nivea herb standardization have been determined on the basis of the following indicators: macroscopic and microscopic features, TLC identification of the main BAS of the raw material (hyperoside, rutin, quercetin and chlorogenic acid), related impurities (not more than 2 %), stems with a diameter of more than 20 mm (not more than 10 %), the loss on drying (not more than 13 %), the total ash (not more than 10 %) and at least 0.5 % flavonoids calculated with reference to rutin.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"4 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82565869","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":"Heterocyclization vs Coupling Reactions: A DNA-Encoded Libraries Case","authors":"Oleksandr V. Oksiuta, A. Pashenko, R. V. Smalii, Dmitry M. Volochnyuk, S. V. Ryabukhin","doi":"10.24959/ophcj.23.275133","DOIUrl":"https://doi.org/10.24959/ophcj.23.275133","url":null,"abstract":"Aim. DNA-encoded libraries technologies (DELT) are gradually becoming an important part of standard drug discovery toolbox. DELT is looking to find its place between classic low-molecular-weight drug candidates on the one hand, and high-molecular-weight antibodies and peptides on the other hand. On its natural path to overcoming the “childhood diseases” typical for every novel technology, DELT has reached a point where the chemical diversity of DNA-encoded libraries (DELs) becomes an important factor to look out for. In this paper, we aim to take a closer look at the chemical diversity of DELs in their present state and find the ways to improve it.Results and discussion. We have identified the DEL-viable building blocks from the Enamine Ltd. stock collection, as well as from Chemspace Ltd. virtual collection, using the SMARTS set, which takes into account all the necessary structural restrictions. Using modern cheminformatics tools, such as Synt-On, we have analyzed the scaffold diversity of both stock and virtual core bi- and tri-functional building blocks (BBs) suitable for DNA-tolerant reactions. The identification of scaffolds from the most recently published on-DNA heterocyclization reactions and analysis of their inclusion into the existing BBs space have shown that novel DNA-tolerant heterocyclizations are extremely useful for expanding chemical diversity in DEL technologies.Conclusions. The analysis performed allowed us to recognize which functional groups should be prioritized as the most impactful when the new BBs are designed. It is also made clear that the development of new DNA-tolerant reactions, including heterocyclizations, have a significant potential to further expand DEL molecular diversity.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"31 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79331923","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":"Biological Activities of Tetrahydroisoquinolines Derivatives","authors":"M. A. Jordaan, Oluwakemi Ebenezer","doi":"10.24959/ophcj.23.268358","DOIUrl":"https://doi.org/10.24959/ophcj.23.268358","url":null,"abstract":"1,2,3,4-Tetrahydroisoquinoline (THIQ) is a common scaffold of many alkaloids isolated from several plants and mammalian species. THIQ derivatives possess a broad spectrum of biological activities, including antitumor, antitubercular, antitrypanosomal, antibacterial, anti-HIV, anti-inflammatory, anti-Alzheimer, and anticonvulsant ones.Aim. To cover updated studies on the biological properties of THIQ derivatives, as well as their structure-activity relationship (SAR), in order to highlight the effect of diverse functional groups responsible for the manifestation of the desired activity.Results and discussion. We have presented the review on biological activities of THIQ. The SAR studies show that the electron-donating, electron-withdrawing and some heterocyclic functional groups on the backbone plays a vital role in modulating the biological potential of the compounds synthesized.Conclusions. This review will help pharmaceutical researchers to synthesize novel and potent compounds containing THIQ scaffold.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89764838","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":"Chemical components of essential oils from aerial parts of Pycnanthemum virginianum and P. californicum (Lamiaceae) plants","authors":"S. Kovtun-Vodyanytska, I. Levchuk, D. Rakhmetov, O. Golubets","doi":"10.24959/ophcj.23.273810","DOIUrl":"https://doi.org/10.24959/ophcj.23.273810","url":null,"abstract":"Aim. The research is aimed at determining the qualitative and quantitative content of essential oils in the aerial part of two species of the genus Pycnanthemum Michx. (Lamiaceae) – P. virginianum (L.) T. Durand & B.D. Jacks. ex B.L. Rob & Fernald and P. californicum Norr. exDurand. The plants were introduced in the M. M. Gryshko National Botanical Garden of National Academy of Sciences of Ukraine (Forest-Steppe zone). These are representatives of the flora of North America, and they are little known in Ukraine. Plants have useful medicinal and nutritional properties, but the biochemical composition of their essential oils has not been sufficiently studied in the world.Materials and methods. In the experiment, the aerial herbal part of plants collected during the flowering phase was used. The quantitative content of the essential oil was determined by the hydrodistillation method, and its qualitative characteristics were found by the GC-MS analysis. The chromatographic profile was obtained on an Agilent Technologies 7890. The component composition of the essential oil was determined on a gas chromatograph with a HP 6890 mass spectrometric detector with a mass spectrometric detector 5973. We used a mass spectrometric detector 1.6 – 800 a.o.m., EI ionization, SIM & Scan mode, “Hewlett Packard”, USA. Identification of essential oil components was performed using the NIST mass spectrum library in combination with AMDIS content-time identification programs.Results and discussion. P. virginianum was found to produce 1.96 ± 0.17 % of essential oil, in which 12 compounds out of 13 were identified; P. californicum had 2.66 ± 0.13 % of essential oil, 13 compounds out of 15 were identified. The essential oil samples obtained have pulegone as the dominant component: P. virginianum – 44.65 %, P. californicum – 86.07 %. In addition to it, they also contain thymol, myrcene, 1.8-cineole, menthone, limonene and other compounds.Conclusions. For the first time, the qualitative and quantitative composition of the essential oils of plants of P. virginianum and P. californicum species introduced in Ukraine has been determined. The results obtained indicate that when introduced plants have a high biosynthesizing ability to produce essential oil. Pulegone has been found to be the dominant component; therefore, the essential oil can be classified as a pulegone-type essential oil. We believe that the raw material of P. virginianum and P. californicum are potentially suitable for use in perfumery, cosmetics, aromatherapy, personal care products, dentistry, and in the pharmaceutical and food industries.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"466 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77525116","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":"The Search for Potential SARS-CoV-2 Inhibitors Using the In Silico Research","authors":"M. Suleiman, A. Fedosov, R. Mohapatra, I. Sych, L. Grinevich, Nataliia P. Kobzar, V. Yaremenko, L. Perekhoda","doi":"10.24959/ophcj.23.276412","DOIUrl":"https://doi.org/10.24959/ophcj.23.276412","url":null,"abstract":"Aim. Using in silico technologies to search for potential SARS-CoV-2 inhibitors among novel tetracyclic ring systems, which are the common core of Crinipellin.Materials and methods. The study object was new compounds previously synthesized via oxidative dearomatization of Crinipellin A. The method of the flexible molecular docking was applied in the study.Results and discussion. Using the molecular docking, the affinity of five compounds for the receptor-ACE2 SARS-CoV-2 (PDB ID: 7DF4), a spike protein SARS-CoV-2 (PDB ID: 1WNC), a PL protein SARS-CoV-2 (PDB ID: 7CJD) and a reverse transcriptase enzyme SARSCoV-2 (PDB ID: 6YYT) was studied. The results of the molecular docking obtained suggest that 8,8-dimethyl-5-(phenylsulfonyl)-3,3a,4,5,8,9-hexahydroindeno[3a,4-b]furan-2(7H)-one may be a potential SARS-CoV-2 inhibitor; it is the basis for its further experimental pharmacological study.Conclusions. The study constitutes one of the stages of searching for SARS-CoV-2 inhibitors. According to the results obtained, a way to search for potential SARS-COV-2 inhibitors based on Crinipellin A derivatives was proposed. Using the most promising compound with hexahydroindeno[3a,4-b]furan core further studies open up another direction for searching for compounds of SARS-COV-2 inhibitors and will save time and laboratory animals while conducting targeted experimental research.","PeriodicalId":16676,"journal":{"name":"Journal of Organic and Pharmaceutical Chemistry","volume":"10 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88801582","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}