Journal of Fluorine Chemistry最新文献

{"title":"Difluorocarbene-enabled synthesis of 18F-radiotracers in positron emission tomography","authors":"Xiaohui Liu ,&nbsp;Chunyang Huan ,&nbsp;Xiaofeng Zhang ,&nbsp;Wei Zhang","doi":"10.1016/j.jfluchem.2024.110253","DOIUrl":"10.1016/j.jfluchem.2024.110253","url":null,"abstract":"<div><p>Positron emission tomography (PET) is a preclinical and clinical imaging technique that is extensively used in biomedical research and disease diagnosis to study and visualize biological and physiological processes. The positron emitter used most frequently for PET imaging is fluorine-18 (¹⁸F) due to its practical 109.8 min half-life, high yield production on fragile biomedical cyclotrons, and well-established ¹⁸F-radiochemistry. Fluorine atom(s) presented in many drugs and biomarkers that provides the opportunity for the development radioligand-labeled with ¹⁸F. Summarized in this paper are difluorocarbene (DFC)-enabled ¹⁸F-radiosynthesis to introduce [¹⁸F]CF₃, [¹⁸F]CF₂ and related motifs in organic molecules and to use them as bioactive radiotracers.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"274 ","pages":"Article 110253"},"PeriodicalIF":1.9,"publicationDate":"2024-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139496617","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}

{"title":"DBU-catalyzed selective β-addition of α-fluoro nitroalkanes to allenoates","authors":"Li-Wen Ning,&nbsp;Yi-Hu Jin,&nbsp;Ren-Jie Wang,&nbsp;Youcan Zhang,&nbsp;Ya Li","doi":"10.1016/j.jfluchem.2024.110255","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110255","url":null,"abstract":"<div><p>An efficient DBU-catalyzed β-addition of α-fluoro nitroalkane compounds to allenoates has been developed. Both γ-substituted and -unsubstituted allenoates participated in the reaction, giving a series of the β-addition products bearing a stereogenic carbon-fluorine structural unit in very good yields. The practicability of the method was also demonstrated.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"274 ","pages":"Article 110255"},"PeriodicalIF":1.9,"publicationDate":"2024-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139493070","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}

{"title":"Compatibility and interaction between C6F12ON2 gas mixture and sealing rubber materials","authors":"Shuangshuang Tian ,&nbsp;Weihao Liu ,&nbsp;Guangyu Deng ,&nbsp;Jiaqi Lan ,&nbsp;Xiaoxing Zhang ,&nbsp;Xiaohan Li ,&nbsp;Zian Yuan","doi":"10.1016/j.jfluchem.2024.110248","DOIUrl":"10.1016/j.jfluchem.2024.110248","url":null,"abstract":"<div><p>The C₆F₁₂O gas mixture has good insulating properties and can replace the strong greenhouse gas sulfur hexafluoride (SF₆) in power equipment. To ensure the safe operation of the equipment, the compatibility between the C₆F₁₂O/N₂ gas mixture and commonly sealing rubber materials Ethylene-Propylene-Diene Monomer (EPDM), Nitrile Butadiene Rubber (NBR), and Fluororubber (FKM)) is an important factor. In this paper, the compatibility between the C₆F₁₂O/N₂ gas mixture and rubber materials at different temperatures is studied. Moreover, the free volume fraction, diffusion coefficient, and radial distribution function are calculated. It is found that there exists a chemical reaction between the C₆F₁₂O/N₂ gas mixture and rubbers, which leads to the appearance of folds or crystalline particles and the accumulation of a large number of F elements on the surface of NBR and EPDM. The simulation results show that the diffusion of the C₆F₁₂O/N₂ gas mixture in the rubber is enhanced with the increase of temperature, and the diffusion coefficient of C₆F₁₂O in NBR is the largest, reaching 33.439 × 10⁻¹¹m²/s. The experimental and theoretical results show that compatibility between the C₆F₁₂O/N₂ gas mixture and FKM is better. FKM will have a better application prospect in C₆F₁₂O/N₂-containing power equipment.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"274 ","pages":"Article 110248"},"PeriodicalIF":1.9,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139411940","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}

{"title":"Efficient synthesis of novel fluorinated phenanthridin-6(5H)-one derivatives and in vitro evaluation of their antiviral activity","authors":"Larisa Gurskaya ,&nbsp;Larisa Politanskaya ,&nbsp;Jiaying Wang ,&nbsp;Polina Ilyina ,&nbsp;Alexandrina Volobueva ,&nbsp;Vladimir Zarubaev","doi":"10.1016/j.jfluchem.2024.110240","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2024.110240","url":null,"abstract":"<div><p>A convenient and efficient method for the synthesis of fluorinated phenanthridin-6(5<em>H</em><span>)-ones from the corresponding 2-isocyanato-1,1′-biphenyls mediated by trifluoromethanesulfonic acid in chlorobenzene is described. The reaction uses readily available starting materials, takes place under very mild reaction conditions (r. t.) and provides access to biologically promising fluorinated heterocycles in good to excellent yields. Synthesized compounds were tested </span><em>in vitro</em> for cytotoxicity in MDCK cell line and for antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1).</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"274 ","pages":"Article 110240"},"PeriodicalIF":1.9,"publicationDate":"2024-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139109287","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}

{"title":"Rh-catalyzed asymmetric cyclopropanation of benzofurans with trifluoromethyl N-triftosylhydrazones","authors":"Caicai He ,&nbsp;Swastik Karmakar ,&nbsp;Dandan Wei ,&nbsp;Wei Zhao ,&nbsp;Xiaolong Zhang ,&nbsp;Xihe Bi","doi":"10.1016/j.jfluchem.2023.110237","DOIUrl":"10.1016/j.jfluchem.2023.110237","url":null,"abstract":"<div><p>An asymmetric dearomative cyclopropanation of benzofuran has been accomplished by a novel catalytic method that relies on using trifluoromethyl <em>N</em>-triftosylhydrazones as carbene sources in the presence of a chiral rhodium catalyst. This reaction produces chiral trifluoromethyl-tethered 2,3-disubstituted benzofuran cyclopropane, which carries versatile pharmacophores 2,3-dihydrobenzofuran and trifluoromethyl-substituted quaternary carbon centers. Notably, this process offers distinct advantages over other existing approaches due to being step-economic and eliminating green-gas N₂ as a harmless coproduct. DFT calculations explain the reason behind the high enantioselectivity during this cyclopropanation reaction.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"273 ","pages":"Article 110237"},"PeriodicalIF":1.9,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113923001525/pdfft?md5=80519f4aba46016beb0c02ac04463280&pid=1-s2.0-S0022113923001525-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139069343","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Extending the substrate scope of palladium-catalyzed arylfluorination of allylic amine derivatives","authors":"Tamás T. Novák ,&nbsp;Thi Cam Tu Nguyen ,&nbsp;Ágnes Gömöry ,&nbsp;Gábor Hornyánszky ,&nbsp;Attila Márió Remete ,&nbsp;Loránd Kiss","doi":"10.1016/j.jfluchem.2023.110239","DOIUrl":"10.1016/j.jfluchem.2023.110239","url":null,"abstract":"<div><p>Fluorinated molecules often show superior bioactivity or ADME (absorption, distribution, metabolism, and excretion) properties compared to their non-fluorinated analogues. In fact, 20–30 % of newly approved drugs and the majority of recently approved agrochemicals are organofluorine compounds. Unsurprisingly, there is great interest in the development of new and/or improved processes for fluorine incorporation. Pd-catalyzed arylfluorination of alkenes is a novel, emerging fluorination method, which simultaneously introduces a fluorine atom and an aryl group into an alkene framework. The aim of the current work was studying, improving, and extending a literature arylfluorination protocol, which originally utilized <em>N</em>-allylated sulfonamide substrates.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"273 ","pages":"Article 110239"},"PeriodicalIF":1.9,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113923001549/pdfft?md5=88c1c7c3bc086f7e01a567a680e8d82d&pid=1-s2.0-S0022113923001549-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139069396","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Group VIII metal difluorocarbene complexes: Synthesis and applications","authors":"Xue Ding ,&nbsp;Yu-Fei Yao ,&nbsp;Weikang Lin ,&nbsp;Zhengqing Ye ,&nbsp;Cheng-Pan Zhang","doi":"10.1016/j.jfluchem.2023.110238","DOIUrl":"10.1016/j.jfluchem.2023.110238","url":null,"abstract":"<div><p>The use of metal catalysts to modulate the generation and reactivity of carbenes has offered a powerful tool for construction of functional molecules. The design and synthesis of relevant transition-metal difluorocarbene complexes have benefited the development and interpretation of transition-metal catalyzed difluorocarbene transfer reactions. Although many achievements have been made in difluorocarbene chemistry, it is still a challenging task to make use of transition-metal difluorocarbenes in synthetic chemistry. To aid interested readers in better understanding the reactivity of transition-metal difluorocarbene species and designing catalytic methods for transfer of difluorocarbene intermediates, we summarize the advances of group VIII metal difluorocarbene complexes. Details include the preparation and properties of these complexes as well as their involvement in organic synthesis.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"273 ","pages":"Article 110238"},"PeriodicalIF":1.9,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113923001537/pdfft?md5=2aec960e62848f278eabc1153617e1d0&pid=1-s2.0-S0022113923001537-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139069464","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Utilization of lateral exit sites for femorally inserted central catheters in pediatric patients: A case report and review of the literature.","authors":"Mark D Weber, Adam S Himebauch, Thomas Conlon","doi":"10.1177/11297298221099138","DOIUrl":"10.1177/11297298221099138","url":null,"abstract":"<p><p>Tunneled femorally inserted central catheters (FICCs) are frequently required for central access in children when upper extremity vessels cannot or should not be cannulated. A recently published decision tool for tunneled FICCs identifies the medial thigh as the preferred exit site. In pediatric patients, this medial exit site may remain at risk of contamination from stool due to anatomic size, and there are no tools developed for FICC exit site decisions specific to children. We present our approach for the placement of the exit site in the far lateral region of the thigh and review previous FICC literature relevant to the pediatric population. In select patients, a lateral approach has the potential to decrease the risk of exit site contamination to prolong catheter viability and reduce patient harm.</p>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"112 1","pages":"323-326"},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77456260","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}

{"title":"Simple practical synthesis of 3,3-difluoropyrrolidine from 2,2-dichlorotrifluoro-1-iodoethane","authors":"Andrey B. Koldobskii ,&nbsp;Sofia M. Morozova ,&nbsp;Olga S. Shilova ,&nbsp;Yuri V. Dankov ,&nbsp;Sergey K. Moiseev","doi":"10.1016/j.jfluchem.2023.110236","DOIUrl":"10.1016/j.jfluchem.2023.110236","url":null,"abstract":"<div><p>Novel simple approach was elaborated for the preparation of 3,3-difluoropyrrolidine hydrochloride starting from commercially available technical 2,2-dichlorotrifluoro-1-iodoethane. Its radical addition to ethylene afforded the corresponding iodide that was transformed into the primary amine. The last one was heated with sodium hydrosulfide to form previously unknown 3,3-difluoropyrrolidine-2-thione which was converted into the target product in high yield. The whole transformation does not require the use of toxic, flammable, explosive and hazardous reagents as well as column chromatography purification. Alternative syntheses have been proposed for the intermediate and target compounds.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"273 ","pages":"Article 110236"},"PeriodicalIF":1.9,"publicationDate":"2023-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113923001513/pdfft?md5=2c92a025f3a943d7d7329e088827dc39&pid=1-s2.0-S0022113923001513-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139027984","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structure and biological property studies of the fluorinated sulfonic esters derived from 2-hydroxy-4-(hydroxy/methoxy)acetophenone as inhibitors of biochemical targets linked to type 2 diabetes mellitus","authors":"Malose J. Mphahlele ,&nbsp;Jackson K. Nkoana ,&nbsp;Samantha Gildenhuys ,&nbsp;Ahmed A. Elhenawy","doi":"10.1016/j.jfluchem.2023.110233","DOIUrl":"https://doi.org/10.1016/j.jfluchem.2023.110233","url":null,"abstract":"<div><p>Small molecule multi-target drugs substituted with fluorine atom/s or fluorine-containing group/s continue to attract considerable interest in medicinal chemistry due to their advantages in the treatment of multifactorial diseases. In this study, fluorine-containing alkyl and benzenesulfonyl chloride building blocks were reacted with 2,4-dihydroxyacetophenone <strong>1a</strong> or 2-hydroxy-4-methoxyacetophenone <strong>1b</strong> to afford the corresponding sulfonic ester derivatives <strong>2a</strong>–<strong>f</strong> and <strong>2g</strong>–<strong>j</strong>, respectively. Detailed crystallographic characterization was performed on a representative compound from each series. The compounds were evaluated through enzymatic assays <em>in vitro</em> for potential to inhibit biochemical targets linked to type 2 diabetes mellitus. Compound <strong>1a</strong> and its 4-(4-fluorophenyl)sulfonyl derivative <strong>2d</strong> exhibited strong and significant inhibitory effect <em>in vitro</em> against α-glucosidase (IC₅₀ = 0.97 ± 0.02 μM and 0.81 ± 0.07 μM, respectively) and α-amylase (IC₅₀ = 6.89 ± 0.04 μM and 4.87 ± 0.02 μM, respectively) compared to acarbose (IC₅₀ = 8.60 ± 0.20 μM and 1.96 ± 0.03 μM, respectively). The presence of a 4-fluorophenylsulfonyl moiety resulted in moderate inhibitory activity for <strong>2d</strong> (IC₅₀ = 27.05 ± 0.01 μM) against protein tyrosine phosphatase 1 beta (PTP1B) compared to the PTP1B inhibitor, suramin (IC₅₀ = 4.63 ± 0.003 μM). The test compounds exhibited strong to moderate nitric oxide radical scavenging activity <em>in vitro</em> against ascorbic acid (IC₅₀ = 5.53 ± 0.03 μM) with IC₅₀ values in the range 0.05–19.30 μM. Compounds <strong>1a</strong> and <strong>2d</strong> did not inhibit superoxide dismutase (SOD) activity. Molecular docking revealed the involvement of hydrophobic, hydrophilic and electrostatic interactions with amino acid residues in the active site of the test enzymes.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"273 ","pages":"Article 110233"},"PeriodicalIF":1.9,"publicationDate":"2023-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113923001483/pdfft?md5=d6ed6f5c5f145980214674ff10f18ece&pid=1-s2.0-S0022113923001483-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138558545","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}