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Visible Light-Induced Decarboxylative Radical Addition of Heteroaromatic Carboxylic Acids to Alkenes at Room Temperature in Two-Molecule Photoredox System. 室温下双分子光氧化还原体系中异芳羧酸与烯烃的脱羧自由基加成反应。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-28 DOI: 10.1002/open.202500232
Daisuke Suzuki, Ryoga Hashimoto, Toshiki Furutani, Mugen Yamawaki, Hirotsugu Suzuki, Yasuharu Yoshimi
{"title":"Visible Light-Induced Decarboxylative Radical Addition of Heteroaromatic Carboxylic Acids to Alkenes at Room Temperature in Two-Molecule Photoredox System.","authors":"Daisuke Suzuki, Ryoga Hashimoto, Toshiki Furutani, Mugen Yamawaki, Hirotsugu Suzuki, Yasuharu Yoshimi","doi":"10.1002/open.202500232","DOIUrl":"https://doi.org/10.1002/open.202500232","url":null,"abstract":"<p><p>The photoinduced decarboxylative radical addition of aryl carboxylic acids, including heteroaromatic carboxylic acids, to electron-deficient alkenes is achieved in a two-molecule photoredox system using a combination of biphenyl (BP) and 9,10-dicyanoanthracene (DCA) without heating. The low efficiency of the back-electron transfer to aryl carboxyl radicals leads to decarboxylation at room temperature. Various heteroaromatic carboxylic acids, including picolinic acid, nicotinic acid, quinoline carboxylic acid, and pyridazine carboxylic acid, are employed as substrates in the photoreaction. Prolonged irradiation without activation by a base successfully leads to decarboxylation by promoting the deprotonation of carboxylic acids by BP<sup>•+</sup>.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500232"},"PeriodicalIF":2.5,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143978238","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Development of an Integrated Computational Pipeline for PARP-1 Inhibitor Screening Using Hybrid Virtual Screening and Molecular Dynamics Simulations. 基于虚拟筛选和分子动力学模拟的PARP-1抑制剂筛选集成计算管道的开发
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-28 DOI: 10.1002/open.202500021
Guan Wang, Jingjing Guo, Feng Xu, Mingjuan Ji
{"title":"Development of an Integrated Computational Pipeline for PARP-1 Inhibitor Screening Using Hybrid Virtual Screening and Molecular Dynamics Simulations.","authors":"Guan Wang, Jingjing Guo, Feng Xu, Mingjuan Ji","doi":"10.1002/open.202500021","DOIUrl":"https://doi.org/10.1002/open.202500021","url":null,"abstract":"<p><p>Despite the promising anticancer properties of PARP-1 inhibitors, their clinical use is hindered by side effects. It is crucial to explore new structural variants of these inhibitors to increase efficacy and minimize side effects, enhancing their clinical viability and therapeutic scope. In this study, we developed a virtual screening workflow that synergistically integrates the capabilities of TransFoxMol, KarmaDock, and AutoDock Vina. This workflow not only streamlines the identification of potential inhibitors but also ensures a systematic approach to prioritizing candidates. Through structural clustering, we identified ten promising PARP-1 inhibitors. Additionally, molecular dynamics simulations and MM/PBSA were employed to elucidate the binding modes of compounds 1, 3, 6, and 9 with PARP-1, providing valuable insights into their interaction mechanisms and supporting future drug development efforts. This workflow serves as a versatile tool for early-stage drug discovery, offering a strategic foundation for the rational design of new PARP-1 inhibitors.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e202500021"},"PeriodicalIF":2.5,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143978767","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Green Synthesis and Application of Biochar Derived from Alien Vegetation Wood for Proton Exchange Membrane Fuel Cells. 外来植被木材生物炭的绿色合成及其在质子交换膜燃料电池中的应用。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-26 DOI: 10.1002/open.202500025
Alunge Gift Sobekwa, Nakedi Albert Mojapelo, Evan David Visser, Ntalane Sello Seroka, Lindiwe Khotseng
{"title":"Green Synthesis and Application of Biochar Derived from Alien Vegetation Wood for Proton Exchange Membrane Fuel Cells.","authors":"Alunge Gift Sobekwa, Nakedi Albert Mojapelo, Evan David Visser, Ntalane Sello Seroka, Lindiwe Khotseng","doi":"10.1002/open.202500025","DOIUrl":"https://doi.org/10.1002/open.202500025","url":null,"abstract":"<p><p>Invasive alien vegetation brought about by various human activities has grown to be a significant threat to the ecosystem and its diversity; therefore, control strategies to combat this threat are being explored. This review aims to investigate the prospect of using biochar specifically from alien vegetation as a support material for the proton exchange membrane (PEM) fuel cell electrocatalyst, highlighting the need to move to green energy and invest in Eco conservation. The use of biochar derived from alien vegetation as carbon support for the platinum (Pt) electrocatalyst for PEM fuel cells is an interesting field that is slowly gaining momentum. Biochar has the potential to be used as a carbon support due to its high specific surface, area, and intrinsic property needed for an electrocatalyst support. The current widely used electrocatalyst, which is Pt supported on carbon black, has shown to suffer from corrosion which weakens the bond between the support and the Pt nanoparticles, leading to instability and resistance; therefore, alternative supports are needed also to decrease the Pt loading as it is expensive. The focus of this review is on the benefits and prospects of these cheap green resources in increasing efforts to conserve the environment.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500025"},"PeriodicalIF":2.5,"publicationDate":"2025-04-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143983643","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Development of G-Ag and C-Ag Nanoparticle-Based Biosensor for Benzoic Acid Detection. 基于G-Ag和C-Ag纳米粒子的苯甲酸检测生物传感器的研制
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-24 DOI: 10.1002/open.202400418
Mehmet Selcuk Erdogan, Muhammed Bekmezci, Nihal Yigit Ertas, Ramazan Bayat, Fatih Sen
{"title":"Development of G-Ag and C-Ag Nanoparticle-Based Biosensor for Benzoic Acid Detection.","authors":"Mehmet Selcuk Erdogan, Muhammed Bekmezci, Nihal Yigit Ertas, Ramazan Bayat, Fatih Sen","doi":"10.1002/open.202400418","DOIUrl":"https://doi.org/10.1002/open.202400418","url":null,"abstract":"<p><p>In this study, an efficient electrochemical sensor for the highly sensitive detection of benzoic acid (BA) is developed using silver nanoparticles (Ag NPs) obtained by two different methods: the green synthesis method (G-Ag) and the chemical synthesis method (C-Ag). Linden flower extract is prepared and used for the biosynthesis of Ag NPs. Sodium borohydride, NaBH<sub>4</sub>, is used as a reducing agent in chemical synthesis. Ag NPs are characterized by the X-ray diffraction (XRD) method, scanning electron microscopy (SEM), Fourier transform infrared (FTIR) spectroscopy, and UV-visible spectrometry. According to the XRD results, the crystal sizes for G-Ag and C-Ag are calculated to be 24.07 and 5.91 nm, respectively. G-Ag and C-Ag NP-modified glassy carbon electrodes (GCEs) and cyclic voltammetry (CV) and differential pulse voltammetry (DPV) are used as electrochemical methods to determine BA. The limits of detection of G-Ag and C-Ag NP-modified GCEs are calculated as 1.67 mM limit of quantification and 10 mM, respectively. The linear ranges of GCEs modified with nanomaterials are determined as 2.40-8.01 mM for C-Ag and 4.84-14.66 mM for G-Ag. The study is significant in that the NPs obtained by the biological synthesis method showed as good activity as the particles synthesized by the chemical method.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2400418"},"PeriodicalIF":2.5,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143969304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Dry Coating with Hydrophilic and Hydrophobized Nanostructured Fumed Alumina (Al2O3) on SiOx/C Anodes for Enhanced Lithium-Ion Battery Performance. 亲水和疏水纳米结构气相氧化铝(Al2O3)在SiOx/C阳极上的干涂层提高锂离子电池性能。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-21 DOI: 10.1002/open.202500170
Ana L Azevedo Costa, Daniel Esken, Tatiana Gambaryan-Roisman, Frank Menzel
{"title":"Dry Coating with Hydrophilic and Hydrophobized Nanostructured Fumed Alumina (Al<sub>2</sub>O<sub>3</sub>) on SiO<sub>x</sub>/C Anodes for Enhanced Lithium-Ion Battery Performance.","authors":"Ana L Azevedo Costa, Daniel Esken, Tatiana Gambaryan-Roisman, Frank Menzel","doi":"10.1002/open.202500170","DOIUrl":"https://doi.org/10.1002/open.202500170","url":null,"abstract":"<p><p>Silicon-based anode materials hold great promise for advancing lithium-ion battery technology due to their high specific capacity, low voltage platform, abundant resources, and environmental benefits. However, their inherent challenges, such as poor electrical conductivity, significant volume expansion, and instability of the solid-electrolyte interphase layer, hinder their widespread commercialization. This study addresses these issues using the dry particle coating method with nanostructured fumed aluminum oxide (Al<sub>2</sub>O<sub>3</sub>), a novel approach with significant potential for commercial scalability. The impact of surface wettability on performance is studied by applying metal oxide coatings, using hydrophilic and hydrophobized surfaces. Electrochemical evaluation shows a significant increase in rate performance and cycle life when the surface coating is applied, with improvements in discharge capacity of around 10% and 17% for hydrophobized and hydrophilic Al<sub>2</sub>O<sub>3</sub> coatings, respectively, after 100 cycles. The Al<sub>2</sub>O<sub>3</sub> coating protects the surface of the active material, preventing particle pulverization, reducing side reactions, and decreasing electrolyte decomposition and hydrofluoric acid content. While overall performance improves with coating, the best results are achieved with the hydrophilic coating, which fosters a more homogeneous microstructured electrode. These findings underscore the potential of the dry particle coating technique with Al<sub>2</sub>O<sub>3</sub> to enhance Si-based anode performance and facilitate commercial application.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500170"},"PeriodicalIF":2.5,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143984895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Fe3O4@Au Core-Shell Nanoparticles with Varying Thicknesses for Application in Computed Tomography Imaging. 合成Fe3O4@Au不同厚度核壳纳米颗粒在计算机断层成像中的应用。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-21 DOI: 10.1002/open.202500166
Nguyen Thi Ngoc Linh, Nguyen Hoa Du, Ngo Thanh Dung, Le Thi Thanh Tam, Pham Hong Nam, Phan Thi Hong Tuyet, Le Trong Lu, Le The Tam
{"title":"Synthesis of Fe<sub>3</sub>O<sub>4</sub>@Au Core-Shell Nanoparticles with Varying Thicknesses for Application in Computed Tomography Imaging.","authors":"Nguyen Thi Ngoc Linh, Nguyen Hoa Du, Ngo Thanh Dung, Le Thi Thanh Tam, Pham Hong Nam, Phan Thi Hong Tuyet, Le Trong Lu, Le The Tam","doi":"10.1002/open.202500166","DOIUrl":"https://doi.org/10.1002/open.202500166","url":null,"abstract":"<p><p>To enhance the resolution of medical images, core-shell Fe<sub>3</sub>O<sub>4</sub>@Au hybrid nanoparticles (HNPs) with gold shells of varying thicknesses are developed. By optimizing synthesis conditions, nanoparticles with uniform size, clear core-shell structure, and high stability in biological environments are obtained. In vitro testing data shows that HNPs with a 5-7 nm-thick gold shell exhibits a high X-ray attenuation. The in vivo efficacy of the Fe<sub>3</sub>O<sub>4</sub>@Au HNPs is tested in liver and kidney tissues in a mouse model for study on drug kinetics. Results demonstrate the effectiveness of Fe<sub>3</sub>O<sub>4</sub>@Au HNPs in enhancing the contrast of computed tomography (CT) images, especially in the liver. Simultaneously, the clearance process of nanoparticles through the kidneys is also observed, opening up the prospect of applying these nanoparticles in image diagnosis and treatment monitoring. Overall, these hybrid particles are a promising candidate for CT imaging techniques.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500166"},"PeriodicalIF":2.5,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955804","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
One-Step Aqueous Synthesis of Glycosyl Pyridinium Salts, Electrochemical Study, and Assessment of Utility as Precursors of Glycosyl Radicals Using Photoredox Catalysis. 一步水法合成糖基吡啶盐,电化学研究及光氧化还原催化作为糖基自由基前体的效用评价。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-21 DOI: 10.1002/open.202500183
Daniel Chong, Paula A Brooksby, Antony J Fairbanks
{"title":"One-Step Aqueous Synthesis of Glycosyl Pyridinium Salts, Electrochemical Study, and Assessment of Utility as Precursors of Glycosyl Radicals Using Photoredox Catalysis.","authors":"Daniel Chong, Paula A Brooksby, Antony J Fairbanks","doi":"10.1002/open.202500183","DOIUrl":"https://doi.org/10.1002/open.202500183","url":null,"abstract":"<p><p>A single step method for the production of unprotected glycosyl pyridinium salts has been developed involving treatment of the unprotected sugar with a pyridine, triethylamine, and either 2-chloro-1,3-dimethylimidazolinium chloride (DMC) or 2-chloro-1,3-dimethyl-1 H-benzimidazol-3-ium chloride (CDMBI) as an activator, in aqueous solution. Reaction efficiency is sensitive to steric effects, and in particular, ortho-substitution of the pyridine ring significantly decreased conversion to product; para-substitution of the pyridine ring is well tolerated. Cyclic voltammetry reveals that glycosyl pyridinium salts possess reduction potentials in the range of -0.9 to -1.4 V versus the standard calomel electrode, which are modulated by the electron effects of ring substituents. However, glycosyl pyridiniums are not found to be useful precursors for the production of glycosyl radicals under photoredox conditions.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500183"},"PeriodicalIF":2.5,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143978776","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Unveiling the Therapeutic Potential of Atractylis aristata Batt. Aqueous Extract: Anti-inflammatory, Antioxidant, Antibacterial, Sedative Activities & Phytochemical Profiling. 揭示白术的治疗潜力。水提取物:抗炎,抗氧化,抗菌,镇静活性和植物化学分析。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-17 DOI: 10.1002/open.202500056
Asma Abid, Nourelhouda Mekhadmi, Randa Mlik, Assia Bentahar, Kamilia Bireche, Bariza Frih, Walid Boussebaa, Aicha Mouane, Nezar Cherrada, Ana Sanches Silva, Messaouda Dekmouche, Lazhar Bechki, Khalid Mashay Al-Anazi, Mohammad Abul Farah, Ahmad Ali
{"title":"Unveiling the Therapeutic Potential of Atractylis aristata Batt. Aqueous Extract: Anti-inflammatory, Antioxidant, Antibacterial, Sedative Activities & Phytochemical Profiling.","authors":"Asma Abid, Nourelhouda Mekhadmi, Randa Mlik, Assia Bentahar, Kamilia Bireche, Bariza Frih, Walid Boussebaa, Aicha Mouane, Nezar Cherrada, Ana Sanches Silva, Messaouda Dekmouche, Lazhar Bechki, Khalid Mashay Al-Anazi, Mohammad Abul Farah, Ahmad Ali","doi":"10.1002/open.202500056","DOIUrl":"https://doi.org/10.1002/open.202500056","url":null,"abstract":"<p><p>Medicinal plants possess the potential to yield bioactive compounds that offer significant health benefits; positioning them as valuable and promising sources for the development of innovative pharmaceutical products. This study aims to comprehensively assess the in vitro and in vivo pharmacological effects of the aqueous extract of the plant Atractylis aristata (AEAA) as well as assessments of its phytochemical composition. UPLC-ESI-MS/MS analysis of AEAA revealed a variety of bioactive compounds, including flavonoids and phenolic acids. In antioxidant assays, AEAA demonstrated considerable activity, with IC<sub>50</sub> values of 0.269±0.05 mg/mL for DPPH scavenging and 0.0376±0.003 mg/mL for hydrogen peroxide radical inhibition. AEAA exhibited strong anti-inflammatory activity in vitro, with an IC<sub>50</sub> value of 2.563 mg/mL in the BSA denaturation test. In vivo, AEAA reduced carrageenan-induced paw edema by 56.51 %, in comparison to an 83.58 % reduction with Ibuprofen®. Antibacterial testing showed AEAA's broad-spectrum activity, with the highest inhibition against Bacillus subtilis (34 mm zone of inhibition). Additionally, AEAA induced significant sedative effects, reducing locomotor activity by 48.98 %. These findings underscore the diverse pharmacological potential in addressing oxidative stress, inflammation, microbial infections, and anxiety of A. aristata, which can be attributed to its rich phytochemical profile.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e202500056"},"PeriodicalIF":2.5,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143966536","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Three-Component 1,2-Methylamidation of Alkynes via Coordinating Activation Strategy. 配位活化策略下炔的三组分1,2-甲基化反应。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-17 DOI: 10.1002/open.202500151
Jing Ren, Kaiyun Liu, Ning Wang, Jinlong Li, Xinyu Long, Chengming Li, Kaizhi Li
{"title":"Three-Component 1,2-Methylamidation of Alkynes via Coordinating Activation Strategy.","authors":"Jing Ren, Kaiyun Liu, Ning Wang, Jinlong Li, Xinyu Long, Chengming Li, Kaizhi Li","doi":"10.1002/open.202500151","DOIUrl":"https://doi.org/10.1002/open.202500151","url":null,"abstract":"<p><p>The selective functionalization of carbon-carbon triple bonds with methyl groups remains a challenging task. Herein, the successful development of a novel copper-catalyzed three-component 1,2-methylamidation of carbon-carbon triple bond is reported. The readily available coupling partners, picolinamides and alkynes with dicumyl peroxide, serve as both the methyl source and oxidant in this difunctional strategy to access methylated enamides; the substrate scope is broad, demonstrating good functional group compatibility. The synthetic utility of the reaction is also demonstrated through the 1,2-methylamidation of alkynes via late-stage functionalization of substrates bearing biologically relevant molecules.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500151"},"PeriodicalIF":2.5,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143992560","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Go for Gold: Development of a Scalable Synthesis of [1-(Ethoxycarbonyl)cyclopropyl] Triphenylphosphonium Tetrafluoroborate, a Key Reagent to Explore Covalent Monopolar Spindle 1 Inhibitors. 寻找黄金:可扩展合成[1-(乙氧羰基)环丙基]三苯基四氟硼酸磷的开发,这是探索共价单极梭形1抑制剂的关键试剂。
IF 2.5 4区 化学
ChemistryOpen Pub Date : 2025-04-16 DOI: 10.1002/open.202500106
Leon Rebhan, Rebekka Fürst, Dieter Schollmeyer, Ricardo A M Serafim, Matthias Gehringer
{"title":"Go for Gold: Development of a Scalable Synthesis of [1-(Ethoxycarbonyl)cyclopropyl] Triphenylphosphonium Tetrafluoroborate, a Key Reagent to Explore Covalent Monopolar Spindle 1 Inhibitors.","authors":"Leon Rebhan, Rebekka Fürst, Dieter Schollmeyer, Ricardo A M Serafim, Matthias Gehringer","doi":"10.1002/open.202500106","DOIUrl":"https://doi.org/10.1002/open.202500106","url":null,"abstract":"<p><p>Covalent approaches have resurged in drug discovery and chemical biology during the last decade. So-called targeted covalent inhibitors typically show a strong and persistent drug-target interaction as well as a high degree of selectivity. In our research group, RMS-07 (8), a First-in-Class covalent inhibitor of the protein kinase threonine tyrosine kinase (TTK)/monopolar spindle 1, which shows promising results in a variety of different solid cancer cell types and will be further optimized in terms of covalent binding kinetics, has recently been developed. However, synthetic accessibility is restricted by a high price and limited availability of [1-(ethoxycarbonyl)cyclopropyl] triphenylphosphonium tetrafluoroborate (10), a key reagent required to assemble the tricyclic core scaffold in a Wittig-type cyclization reaction. This reagent is also described as a valuable synthon for the synthesis of a range of ring systems with interesting applications in medicinal chemistry. However, reliable procedures for its large-scale synthesis are scarce. Only one prior report describes the synthesis of reagent 10, and it contains limited experimental details, making it challenging to reproduce and scale up. Herein, a concise and reproducible decigram-scale synthetic protocol for accessing key reagent 10 is described.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":" ","pages":"e2500106"},"PeriodicalIF":2.5,"publicationDate":"2025-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143963104","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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