Article
Chemistry, Organic
Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun, Jinxing Ye
Summary: This study developed a practical continuous flow protocol for efficient synthesis of various functionalized piperidines within minutes, with high yields and enantiomeric excess. The scalability and utility of the process were demonstrated through the efficient synthesis of a drug precursor.
Article
Chemistry, Applied
Kossi Efouako Soklou, Hamid Marzag, Beatrice Vallee, Sylvain Routier, Karen Ple
Summary: Gold(I) catalysis was used for the intramolecular cyclization of tertiary alcohols with terminal alkynes to form diverse aza-spirocycles. The reaction produced both sulfonylated and acylated spirocyclic nitrogen derivatives, demonstrating the robustness of the method. These compounds were then incorporated into biologically relevant scaffolds to give the first selective spirocyclic inhibitors of LIMK1.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Franziska Spruner von Mertz, Ricardo Molenda, Sebastian Boldt, Alexander Villinger, Peter Ehlers, Peter Langer
Summary: A series of previously unknown 5,14-diphenylbenzo[j]naphtho[2,1,8-def][2,7]phenanthrolines, incorporating a 5-azatetracene and a 2-azapyrene subunit, were successfully synthesized using Pd-catalyzed cross-coupling reactions and a one-pot Povarov/cycloisomerization reaction. This synthetic approach enables extensive diversification of the heterocyclic core structure. The optical and electrochemical properties of these compounds were investigated through experimental and computational studies, revealing their closer electronic and optical resemblance to 2-azapyrenes rather than the typical characteristics of 5-azatetracene moieties.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Merlin Kleoff, Lisa Boeser, Linda Baranyi, Philipp Heretsch
Summary: A metal-free synthesis method for benzotriazoles in flow using azides and in situ generated arynes is reported. The modular access to benzotriazoles is provided by employing different substitution patterns of the azide and aryne coupling partners. The safety profile of the process is improved by minimizing thermal strain of hazardous azides and accumulation of reactive intermediates through short reaction times in flow. The scalability of the reaction is also demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Dipendu Mandal, Zahid Hussain, Yong-an Luo, Yile Wu, Douglas W. W. Stephan
Summary: The reactions of boranes with azodicarboxylates or azodicarbonylamide provide easy access to NBO heterocyclic compounds. The formation mechanism is proposed to involve transient hydroboration or hydroalumination of the N=N double bond.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Medicinal
Ebrahim Saeedian Moghadam, Katayoon Mireskandari, Raid Abdel-Jalil, Mohsen Amini
Summary: This article provides a comprehensive review of recent reports on bioactive pyrrole derivatives, categorizing them based on their direct pharmacologic targets. It presents around seventy different biologic targets for pyrrole-containing compounds, making it helpful for medicinal chemists in their design and development of novel bioactive compounds.
MINI-REVIEWS IN MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bo-Han Zhu, Sheng-Bing Ye, Min-Ling Nie, Zhong-Yang Xie, Yi-Bo Wang, Peng-Cheng Qian, Qing Sun, Long-Wu Ye, Long Li
Summary: In this study, an unprecedented I-2-catalyzed cycloisomerization of ynamides is developed, leading to the synthesis of various functionalized bis(indole) derivatives in good to excellent yields. This reaction represents the first molecular-iodine-catalyzed tandem complex alkyne cycloisomerizations and a chemoselective cycloisomerization of tryptamine-ynamides involving distinct C(sp(3))-C(sp(3)) bond cleavage and rearrangement. Chiral tetrahydropyridine frameworks containing two stereocenters are also obtained with moderate to excellent diastereoselectivities and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jacob C. Hood, Maksim V. Anokhin, Douglas A. Klumpp
Summary: N-Heterocyclic alcohols have been proven to be excellent substrates for superacid-promoted Friedel-Crafts reactions. The ionization of N-heterocyclic alcohols produces reactive, dicationic intermediates, leading to good to excellent yields of arylation products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Klaus Paschek, Mijin Lee, Dmitry A. Semenov, Thomas K. Henning
Summary: This study investigates aqueous chemistry within carbonaceous planetesimals and proposes a new reaction mechanism for the synthesis of vitamin B-3. Through experiments and thermodynamic calculations, the study examines the favorability of this new pathway and compares the predicted vitamin B-3 abundances with measured values in asteroids and meteorites. The findings highlight the importance of understanding prebiotic organic matter formation in meteorites.
Article
Chemistry, Multidisciplinary
Mateusz Dyguda, Artur Przydacz, Lukasz Albrecht
Summary: This manuscript describes the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines. The method involves the aminocatalytic activation of 2-alkyl-3-furfurals and proceeds via the formation of dearomatized dienamine intermediate. The obtained cycloadducts can be further transformed into tetrahydrofuropyridines or functionalized cinnamates. The mechanism of the transformation was confirmed through DFT calculations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mateusz Dyguda, Artur Przydacz, Lukasz Albrecht
Summary: This manuscript describes the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines. The developed approach utilizes aminocatalytic activation of 2-alkyl-3-furfurals that proceeds via formation of the dearomatized dienamine intermediate. The obtained cycloadducts can be further transformed into tetrahydrofuropyridines or functionalized cinnamates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Martin S. Faillace, Noelia M. Ceballos, Natalia B. Shustova, Walter J. Pelaez
Summary: In this study, a regiospecific and stereoselective synthesis method for novel pyrrolo thioxoimidazolidinones with promising biological activities was reported. These compounds have great potential applications due to the pharmaceutical properties of the thioxoimidazolidinone core. The reaction between different thioxoimidazolidinones and trans-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (ETFBO) yielded bicyclic 1,3-diaza heterocycles with a trifluoromethyl (CF3) moiety. Both experimental analysis and theoretical calculations were conducted to reveal the reaction mode of this building block and the underlying mechanism for the observed reactions. Remarkably, the unusual mechanism retained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilic reactions reported in the literature.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Katie A. A. Spence, Marie Hoffmann, Neil K. K. Garg
Summary: We report a concise approach to the synthesis of phenanthroindolizidine alkaloids, utilizing the interception of strained azacyclic alkynes in Pd-catalyzed reactions. Two types of strained intermediates, a functionalized piperidyne and a new strained intermediate, indolizidyne, were evaluated. These efforts resulted in the successful synthesis of three natural products: tylophorine, tylocrebine, and isotylocrebine, demonstrating the successful combination of strained azacyclic alkyne chemistry with transition-metal catalysis for the construction of complex heterocycles.
Article
Chemistry, Multidisciplinary
Franziska K. Merkt, Flaminia Mazzone, Shabnam Shaneh Sazzadeh, Lorand Bonda, Larissa K. E. Hinz, Irina Gruber, Karin Buchholz, Christoph Janiak, Klaus Pfeffer, Thomas J. J. Mueller
Summary: A gold-catalyzed cycloisomerization reaction was used to synthesize a series of luminescent silylated heterocycles, whose optical properties can be tuned by different functional groups. These compounds also showed promising anti-parasitic activities, making them potential candidates for novel anti-parasitic therapies.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Oksana Reznichenko, Denis Leclercq, Jaime Franco Pinto, Liliane Mouawad, Valerie Gabelica, Anton Granzhan
Summary: G-quadruplexes, secondary structures adopted by guanine-rich DNA and RNA sequences, have attracted increasing interest as potential drug targets. In this study, a simple method of parallel synthesis was developed to generate ready-to-screen libraries of cationic acylhydrazones. Using this method, a combinatorial library of 90 bis(acylhydrazones) was synthesized and screened against five different nucleic acid structures. Three novel G4 ligands with promising interactions with G4-DNAs of different topologies were identified and studied in detail by various biophysical techniques.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Chun-Lin Deng, Xiao-Shui Peng, Henry N. C. Wong
Article
Chemistry, Multidisciplinary
Chun-Lin Deng, Jeremy P. Bard, Jessica A. Lohrman, Joshua E. Barker, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Chun-Lin Deng, Jeremy P. Bard, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Wataru Nojo, I. David Reingold, Jeremy P. Bard, Daniel T. Chase, Chun-Lin Deng, Michael M. Haley
Article
Chemistry, Organic
Chun-Lin Deng, Jeremy P. Bard, Lev N. Zakharoy, Darren W. Johnson, Michael M. Haley
Article
Chemistry, Organic
Jeremy P. Bard, Hannah J. Bates, Chun-Lin Deng, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Jeremy P. Bard, Jenna L. Mancuso, Chun-Lin Deng, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley
SUPRAMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Adam T. Brockett, Chunlin Deng, Michael Shuster, Suvenika Perera, Delaney DiMaggio, Ming Cheng, Steven Murkli, Volker Briken, Matthew R. Roesch, Lyle Isaacs
Summary: Two new acyclic sulfated acyclic CB[n]-type receptors were synthesized and TetM0 was found to have the highest binding affinity towards methamphetamine, fentanyl, MDMA and mephedrone. TetM0 showed no cytotoxicity in vitro and in vivo, and had the potential to reduce hyperactivity in mice treated with methamphetamine.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Chun-Lin Deng, Ming Cheng, Peter Y. Zavalij, Lyle Isaacs
Summary: This study investigated the complexation between a water soluble pillararene host and a panel of hydrophobic cationic guests through H-1 NMR spectroscopy and isothermal titration calorimetry. The findings revealed the formation of 1:1 complexes driven by favorable enthalpic contributions, with Ka values in the 10^4-10^9 M^-1 range. This thermodynamic dataset is used as blinded data for the SAMPL9 challenge.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Adam T. Brockett, Weijian Xue, David King, Chun-Lin Deng, Canjia Zhai, Michael Shuster, Shivangi Rastogi, Volker Briken, Matthew R. Roesch, Lyle Isaacs
Summary: Pillar[6]MaxQ (P6AS) functions as an in vivo sequestration agent for methamphetamine and fentanyl, forming tight complexes with these drugs. P6AS exhibits good in vitro biocompatibility and can ameliorate the hyperlocomotion caused by methamphetamine and fentanyl in mice experiments. P6AS has significant potential for development as a broad-spectrum in vivo sequestration agent.
Article
Chemistry, Organic
David King, Chelsea R. Wilson, Lukas Herron, Chun-Lin Deng, Shams Mehdi, Pratyush Tiwary, Fraser Hof, Lyle Isaacs
Summary: In this study, we investigated the molecular recognition properties of P[n]MQ towards (methylated) amino acids, amino acid amides, and post-translationally modified peptides using various techniques. Our findings showed that P6MQ is a strong receptor for N-methylated amino acid side chains, specifically recognizing the H3K4Me(3) peptide with high affinity (K-d = 16 nM) in phosphate buffered saline.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Chun-Lin Deng, Steven L. Murkli, Lyle D. Isaacs
CHEMICAL SOCIETY REVIEWS
(2020)
Article
Chemistry, Organic
Jeremy P. Bard, Chun-Lin Deng, Hannah C. Richardson, Jacob M. Odulio, Joshua E. Barker, Lev N. Zakharov, Paul H. -Y. Cheong, Darren W. Johnson, Michael M. Haley
ORGANIC CHEMISTRY FRONTIERS
(2019)
Article
Chemistry, Multidisciplinary
Jessica A. Lohrman, Chun-Lin Deng, Trevor A. Shear, Lev N. Zakharov, Michael M. Haley, Darren W. Johnson
CHEMICAL COMMUNICATIONS
(2019)
Meeting Abstract
Chemistry, Multidisciplinary
Chun-Lin Deng, Jessica Lohrman, Jeremy Bard, Michael Haley, Darren Johnson
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)
