Article
Chemistry, Multidisciplinary
Jin Young Chai, Hyojin Cha, Sung-Sik Lee, Young-Ho Oh, Sungyul Lee, Dae Yoon Chi
Summary: The synthesis of fluorine-18 labeled fluoroform with high molar activity is essential for the development of fluorine-18 labeled aryl-CF3 radiopharmaceuticals for PET imaging. The study proposed a strategy for synthesizing fluoroform and elucidated the mechanism of the fluorination reaction, showing the superiority of the S(N)2 pathway. The research demonstrated the potential for preparing fluorine-18 labeled fluoroform with high molar activity through experimental and theoretical studies.
Article
Chemistry, Multidisciplinary
Harjeet S. Soor, Diego B. Diaz, Katherine I. Burton, Andrei K. Yudin
Summary: The ongoing search for underdeveloped functional group combinations has led to the discovery of alpha-fluorinated aminoalkylboronic acids, a new class of molecules featuring the B-CF linkage. These compounds can be generated through electrophilic fluorination and show stability and unique structural properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Qinghe Liu, Taige Kong, Chuanfa Ni, Jinbo Hu
Summary: A reagent-controlled highly stereoselective reaction was reported for the synthesis of enantiomerically enriched alpha-difluoromethyl amines using (S)-difluoromethyl phenyl sulfoximine 1 and imines. This approach offers high efficiency, high stereoselectivity, and a broad substrate scope, possibly achieved through a non-chelating transition state.
Article
Chemistry, Organic
Amaury Dubart, Gwilherm Evano
Summary: This method involves the activation of amides with triflic anhydride and 2-halo-pyridine, trapping of the resulting ions, and subsequent transformation into alpha-fluorinated ketones, esters, and amides, along with the production of enantioenriched products.
Article
Chemistry, Multidisciplinary
J. R. Alexander, P. Kevorkian, J. J. Topczewski
Summary: The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield alpha-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction is regioselective and the products result from an initial [3,3] rearrangement. Over 15 examples have been demonstrated with yields ranging from 37% to 86%.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jay S. Wright, Richard Ma, E. William Webb, Wade P. Winton, Jenelle Stauff, Kevin Cheng, Allen F. Brooks, Melanie S. Sanford, Peter J. H. Scott
Summary: This report presents the development of a Zn(OTf)(2)-mediated method for converting alpha-tertiary haloamides to the corresponding alpha-tertiary fluoroamides. Under optimized conditions, high radiochemical conversion can be achieved. This method has been successfully applied to prepare various model radiofluorides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
George Hutchinson, Carla Alamillo-Ferrer, Martin Fernandez-Pascual, Jordi Bures
Summary: The Nanjing Huamu Football Team has developed a number of outstanding players over the past 7 years and has made significant contributions to the local youth football movement.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Guanyu Zhang, Maodie Wang, Petia Bobadova-Parvanova, Frank R. Fronczek, Kevin M. Smith, M. Graca H. Vicente
Summary: The synthesis and reactivity of 3,8-dibromo-dodecafluoro-benzo-fused BOPHY 2 were reported in this study, with reactions involving various nucleophiles and Pd(0)-catalyzed cross-coupling reactions. The resulting perfluoro-BOPHY derivatives showed different reactivities under different conditions, indicating potential applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Neshat Rozatian, David R. W. Hodgson
Summary: This review discusses the experimental approaches used to determine the reactivities of N-F class electrophilic fluorinating reagents, focusing on recent kinetics studies. Critical evaluations are made against different experimental and theoretical approaches, highlighting the opportunities for achieving more efficient synthetic processes through kinetic understanding.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Naoki Shida, Hiroaki Takenaka, Akihiro Gotou, Tomohiro Isogai, Akiyoshi Yamauchi, Yosuke Kishikawa, Yuuya Nagata, Ikuyoshi Tomita, Toshio Fuchigami, Shinsuke Inagi
Summary: This study investigates the fundamental properties of alkali metal fluorides (MF, M = Cs, K) dissolved in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) or in 3,3,3-trifluoroethanol (TFE), including solubility, conductivity, and viscosity. The solid-state structures of single crystals obtained from CsF/HFIP and CsF/TFE are described for the first time, providing insights into the interactions between fluorinated alcohols and CsF. Additionally, successful applications in electrochemical fluorination reactions are demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shuai Song, Ya Li, De-Yin Chen, Xiao-Ping Wang, Yong-Liang Liu, Ling-Yan Chen
Summary: The study presents a novel approach to synthesizing compounds containing both alpha-amidoacrylate and 3-ylideneoxindole motifs through a cascade process. The protocol demonstrated a broad substrate scope, with various 3-fluorooxindoles suitable for the reaction.
Article
Engineering, Environmental
Emily L. Marron, Jean Van Buren, Amy A. Cuthbertson, Emily Darby, Urs von Gunten, David L. Sedlak
Summary: Chemical disinfectants used in water treatment can lead to the formation of transformation products, such as alpha,beta-unsaturated carbonyl compounds, that readily react with free chlorine and bromine, transforming into other products to a significant extent through free chlorine in distribution systems. Experiments show that these reactions may result in products that no longer contain unsaturated carbons.
ENVIRONMENTAL SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Applied
Tsugio Kitamura, Daichi Kitamura, Juzo Oyamada, Masahiro Higashi, Yosuke Kishikawa
Summary: A new N-F reagent, N,N'-difluoro-2,2';-bipyridinium bis(tetrafluoroborate), for iodoarene-catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3-dicarbonyl compounds, giving 1,2-difluorinated alkanes, geminal difluorinated compounds, 2-fluorinated-1,3-dicarbonyl compounds in good to high yields, respectively. The present N-F reagent can be recovered as 2,2'-bipyridine.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Saul Alberca, Esteban Matador, Javier Iglesias-Siguenza, Ma de Gracia Retamosa, Rosario Fernandez, Jose M. Lassaletta, David Monge
Summary: Alpha-keto hydrazones and alpha,beta-unsaturated gamma-keto hydrazones are suitable pro-nucleophiles for asymmetric cross-aldol reactions. A quinidine-derived primary amine catalyst yields tertiary trifluoromethylated alcohols with good-to-excellent yields and high enantioselectivities, leading to various appealing fluorinated compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Medicinal
Sandip S. Shinde, Kim-Viktoria Bolik, Simone Maschauer, Olaf Prante
Summary: This study developed TBMA-I as a PTC for F-18-fluorination reactions, demonstrating its favorable elution efficiency and potential application in labeling reactions.
Article
Biochemistry & Molecular Biology
Felix P. Mayer, Marco Niello, Daniela Cintulova, Spyridon Sideromenos, Julian Maier, Yang Li, Simon Bulling, Oliver Kudlacek, Klaus Schicker, Hideki Iwamoto, Fei Deng, Jinxia Wan, Marion Holy, Rania Katamish, Walter Sandtner, Yulong Li, Daniela D. Pollak, Randy D. Blakely, Marko D. Mihovilovic, Michael H. Baumann, Harald H. Sitte
Summary: Increasing extracellular levels of serotonin can ameliorate symptoms of depression and anxiety-related disorders. The study found that certain ring-substituted cathinones show preference for the release of serotonin and exert 5-HT-associated effects in behavioral models. These compounds have low abuse liability and potential for adverse events.
MOLECULAR PSYCHIATRY
(2023)
Article
Multidisciplinary Sciences
Marco Niello, Spyridon Sideromenos, Ralph Gradisch, Ronan O'Shea, Jakob Schwazer, Julian Maier, Nina Kastner, Walter Sandtner, Kathrin Jantsch, Carl R. Lupica, Alexander F. Hoffman, Gert Lubec, Claus J. Loland, Thomas Stockner, Daniela D. Pollak, Michael H. Baumann, Harald H. Sitte
Summary: By using various in vitro, computational, and in vivo approaches, we found that the drug-binding kinetics of S-enantiomers of pyrovalerone analogs at DAT correlate with the time-course of in vivo psychostimulant action in mice. In particular, the slow dissociation (i.e., slow koff) of S-enantiomers of pyrovalerone analogs from DAT can predict their more persistent in vivo effects compared to cocaine and methylphenidate. Overall, our findings highlight the critical importance of drug-binding kinetics at DAT in determining the in vivo profile of effects produced by psychostimulant drugs.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2023)
Review
Chemistry, Multidisciplinary
Philipp Spiess, Saad Shaaban, Daniel Kaiser, Nuno Maulide
Summary: Umpolung is a term describing the reversal of innate polarity, which has become an important tool in synthetic organic chemistry. In this Account, the authors provide an overview of established methods and summarize their findings in the rapidly developing field of umpolung of carbonyl derivatives. They focus on the alpha-umpolung of amides enabled by electrophilic activation and the enolonium chemistry of ketones enabled by hypervalent iodine reagents. The authors discuss the challenges and achievements of these reactions, as well as mechanistic aspects. Rating: 8/10.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Minghao Feng, Anthony J. J. Fernandes, Ana Sirvent, Eleonora Spinozzi, Saad Shaaban, Nuno Maulide
Summary: We present a simple method for the direct amination of unfunctionalized, native carbonyls (amides and ketones) by transferring a free amino group (NH2) from a commercially available nitrogen source. Mild conditions enable the production of primary a-amino carbonyls, allowing for diverse in situ functionalization reactions, such as peptide coupling and Pictet-Spengler cyclization, that take advantage of the presence of the unprotected primary amine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Philipp Spiess, Ana Sirvent, Irmgard Tiefenbrunner, Jules Sargueil, Anthony J. Fernandes, Ana Arroyo-Bondia, Ricardo Meyrelles, David Just, Alexander Prado-Roller, Saad Shaaban, Daniel Kaiser, Nuno Maulide
Summary: p-Toluenesulfonyl (Tosyl) and nitrobenzenesulfonyl (Nosyl) are widely used sulfonyl protecting groups for amines in organic synthesis. However, p-toluenesulfonamides are difficult to remove in multistep synthesis, while nitrobenzenesulfonamides are not stable under various reaction conditions. In this study, we introduce a new sulfonamide protecting group called Nms, which overcomes these limitations and shows superiority in terms of stability and cleavability.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Nuno Maulide, Irmgard Tiefenbrunner, Bogdan R. Brutiu, Tobias Stopka
Summary: We have developed an isothiouronium salt reagent for the straightforward synthesis of cyanomethyl thioesters with excellent functional group tolerance and without the need for thiols. Furthermore, we demonstrate that the obtained products can be used for amide synthesis in either a two-step or one-pot approach.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Phillip S. Grant, Ricardo Meyrelles, Oliver Gajsek, Gerhard Niederacher, Boris Maryasin, Nuno Maulide
Summary: Cationic cyclopropanation is a rare but important biosynthetic pathway involving the formation of a new sigma-C-C bond through the elimination of carbocations. Despite the historical influence of bioinspired synthetic chemistry, cationic cyclopropanation has not been widely used due to the preference of carbocations for competing elimination pathways. In this study, we conducted a synthetic and computational investigation of cationic cyclopropanation using 6,8-cycloeudesmanes as a platform, and successfully applied it to the synthesis of complex cyclopropanes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
N. J. Clauss, F. P. Mayer, W. A. Owens, M. Vitela, K. M. Clarke, M. A. Bowman, R. E. Horton, D. Gruendemann, D. Schmid, M. Holy, G. G. Gould, W. Koek, H. H. Sitte, L. C. Daws
Summary: Concurrent cocaine and alcohol use is a dangerous drug combination that increases extracellular monoamines. Ethanol's ability to inhibit monoamine uptake is dependent on the organic cation transporter 3 (OCT3), while cocaine blocks DAT, NET, and SERT. These findings suggest OCT3 as a potential target for therapeutic intervention in ethanol and ethanol/cocaine use disorders.
MOLECULAR PSYCHIATRY
(2023)
Article
Medicine, General & Internal
Michael Eigenschink, Luise Bellach, Sebastian Leonard, Tom Eric Dablander, Julian Maier, Fabian Dablander, Harald H. Sitte
Summary: This study investigates the popularity, usage, and perceived scientific support of Traditional Chinese Medicine (TCM) in Austria. It found that TCM is widely known and used by a substantial proportion of the population, but there is a disparity between the public perception of TCM as scientific and evidence-based studies. It emphasizes the importance of distributing unbiased, science-driven information.
Article
Psychiatry
Jacqueline D. Keighron, Jordi Bonaventura, Yang Li, Jae-Won Yang, Emily M. M. DeMarco, Melinda Hersey, Jianjing Cao, Walter Sandtner, Michael Michaelides, Harald H. H. Sitte, Amy Hauck Newman, Gianluigi Tanda
Summary: Typical and atypical dopamine uptake inhibitors (DUIs) have different effects on behavior, neurochemistry, and addiction potential due to their preference for distinct conformations of the dopamine transporter (DAT) to form ligand-transporter complexes. Cocaine and typical psychostimulants reduce dopamine clearance rate, but only typical DUIs stimulate evoked dopamine release, unrelated to DAT affinity. Pretreatment with a CaMKII alpha inhibitor blunts the stimulatory effects of cocaine on dopamine release, suggesting a role for this kinase in modulating cocaine's effects. Atypical DUIs blunt cocaine's effects, indicating a unique mechanism underlying their potential as medications for psychostimulant use disorder.
TRANSLATIONAL PSYCHIATRY
(2023)
Article
Chemistry, Multidisciplinary
Minghao Feng, Anthony J. Fernandes, Ricardo Meyrelles, Nuno Maulide
Summary: We report a new method for preparing chiral α-amino amides by directly aminating amides using chiral sulfinamides. This method involves a [2,3]-sigmatropic rearrangement of a crucial sulfonium intermediate. Quantum chemical calculations provide predictive insights into the important E/Z selectivity of the amino-vinyloxy-sulfonium species.
Article
Pharmacology & Pharmacy
Francesca R. Brugnoli, Marion Holy, Marco Niello, Julian Maier, Marcus Hanreich, Mario Menzel, Matthias Haberler, Niklas Zulus, Thomas Pickl, Christa Ivanova, Lisa D. Muiznieks, Benjamin Garlan, Harald H. Sitte
Summary: To address the drawbacks of current techniques in studying the interaction of monoamine transporters, researchers developed an automated microfluidic platform for more accurate and standardized cell-based assays. The platform successfully validated the effects of control compounds such as D-Amphetamine, GBR12909, p-chloroamphetamine, and paroxetine on the two transporters.
BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Miran Lemmerer, Nuno Maulide
Summary: The combination of Lewis bases with alpha, beta-unsaturated carbonyls enables the in-situ generation of enolates, eliminating the need for strong Bronsted bases. This approach has been widely employed in arylation reactions in various contexts. This conceptual article provides an overview of the developed strategies, highlighting their features.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
David Just, Carlos R. Goncalves, Uros Vezonik, Daniel Kaiser, Nuno Maulide
Summary: A simple method for the direct formation of aminolactones from unactivated alkenes has been reported in this study, filling the gap in this field. The method utilizes cheap and readily available reactants, and exhibits excellent functional group tolerance and chemoselectivity. The synthetic versatility of the products has been demonstrated through a range of transformations.
Article
Neurosciences
Felix P. Mayer, Marco Niello, Simon Bulling, Yuan-Wei Zhang, Yang Li, Oliver Kudlacek, Marion Holy, Fatemeh Kooti, Walter Sandtner, Gary Rudnick, Diethart Schmid, Harald H. Sitte
Summary: This study provides further insights into the pharmacology of mephedrone at hDAT and hSERT. It was found that mephedrone induces carrier-mediated release via hDAT and hSERT and is sensitive to protein kinase C inhibitor. Additionally, mephedrone displays greater efficacy as a releaser at hSERT than at hDAT, indicating its higher activity at hSERT.