Article
Chemistry, Organic
Laura Buglioni, Marko Beslac, Timothy Noel
Summary: The electrochemical synthesis of aryl azoles was successfully conducted in a microflow reactor for the first time, avoiding the need for homogeneous transition-metal-based catalysts. By implementing a microflow setup, shorter residence times and good to excellent yields of various azolated compounds were achieved.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mikhail Feofanov, Vladimir Akhmetov, Ryo Takayama, Konstantin Amsharov
Summary: A facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes is described, involving two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Leonie O'Sullivan, Ketul V. Patel, Ben C. Rowley, Duncan K. Brownsey, Evgueni Gorobets, Benjamin S. Gelfand, Jeffrey F. Van Humbeck, Darren J. Derksen
Summary: A regioselective route to C3-hydroxyarylated pyrazoles was developed using mild conditions, allowing for the synthesis of a JAK 1/2 inhibitor in just 4 steps from commercially available starting materials.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kan Zhang, Mingming Yang, Yanxiu Yao, Binxun Yu, Yanyan Wang, Huaming Sun, Weiqiang Zhang, Guofang Zhang, Ziwei Gao
Summary: Benzodiazepines are commonly found in biologically active compounds and pharmaceutical agents. Direct synthesis of these compounds from simple and easily accessible starting materials has been a challenge in synthetic chemistry. In this study, a highly efficient synthetic method for benzodiazepines was developed, involving a multi-step reaction sequence and specific catalysts, to achieve the synthesis under mild conditions.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Juan Camilo Arango-Daza, Carles Lluna-Galan, Luis Izquierdo-Aranda, Jose R. Cabrero-Antonino, Rosa Adam
Summary: A heterogeneous catalytic system for the acceptorless dehydrogenative condensation between N,N'-disubstituted ureas and 1,2-diols to produce imidazolones was developed. The designed palladium nanoaggregates on an alumina matrix showed good activity and selectivity, with wide applicability and moderate to good yields. Mechanistic studies and characterization were performed, revealing the key factors for the catalyst's activity. Furthermore, a Pd-Zn cooperation effect was described, and bimetallic materials were also designed and characterized properly.
Article
Chemistry, Multidisciplinary
Grace L. Trammel, Prashansa B. Kannangara, Dmytro Vasko, Oleksandr Datsenko, Pavel Mykhailiuk, M. Kevin Brown
Summary: Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates, resulting in the synthesis of versatile borylated saturated N-heterocycles with good regio- and diastereoselectivities. The Cu/Pd dual catalytic reaction enables the synthesis of borylated, alpha-arylated azetidines, while the Ni-catalysed arylboration reaction efficiently functionalizes 5-, 6-, and 7-membered enecarbamates. The use of additives in the Cu/Pd system allows for a broader scope of reactions, and the products can be further manipulated to access biologically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yixin He, Zhichun Shangguan, Zhao-Yang Zhang, Mingchen Xie, Chunyang Yu, Tao Li
Summary: Azobispyrazoles are a new family of molecular photoswitches with (near-)quantitative bidirectional photoconversion and widely tunable Z-isomer thermal half-lives. The two five-membered rings in their structure weaken intramolecular steric hindrance, providing new possibilities for engineering the geometric and electronic structure of azo photoswitches. Their twisted Z-isomers allow for complete Z -> E photoisomerization, and their thermal stability can be adjusted broadly, overcoming the conflict between photoconversion and Z-isomer stability encountered by mono-heteroaryl azo switches.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Seonghyeon Nam, Ikyon Kim
Summary: A modular approach was used to successfully synthesize a polyfunctionalized indolizine-indole fused system, using readily available compounds and a combination of a one pot three-component assembly and Cu-catalyzed double C-N coupling reactions. This method allows for the formation of multiple new bonds in a simple and efficient manner.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Benjamin N. Atkinson, Nicky J. Willis, Jennifer Smith, Rebecca Gill, Jody Ali, Zhou Xu, Ping-Shan Lai, Paul Fish
Summary: In this study, 1-Phenyl-1H-1,2,3-triazole 1 (ARUK3001185) was prepared on a large scale using both copper-catalyzed azide-alkyne cycloaddition (CuAAC) and a Clark modification of the Sakai reaction. The Sakai-Clark method proved to be superior, with operational simplicity, metal-free conditions, and avoiding the use of aryl azide 7. The method was reliable for the large-scale production of >100 g of 1 with good efficiency and high purity.
Article
Chemistry, Medicinal
Ying Wang, Isabella Haight, Rishi Gupta, Anil Vasudevan
Summary: Building blocks are crucial in drug molecule design, playing a significant role in determining the quality of the final compound. Analysis of the building blocks used in medicinal chemistry can provide insights into synthetic tractability and accessibility, as well as identify opportunities for incorporating underrepresented building blocks to gain intellectual and competitive advantages in drug discovery.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Neil R. Judge, Geraud Chacktas, Ling Ma, Anke Schink, Rainer Buckpesch, Dirk Schmutzler, Anu B. Machettira, Hansjoerg Dietrich, Elisabeth Asmus, Donald Bierer, Michael C. McLeod
Summary: The study reports the synthesis of a novel library of fully substituted 3-hydroxypyrazoles and their herbicidal efficacy evaluation. A series of compounds with different substituents were successfully synthesized and evaluated, leading to the identification of a lead herbicidal compound.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Anastasiya Fedinchyk, Maksym Herasymchuk, Vladyslav O. Smirnov, Kostiantyn P. Melnykov, Dmytro Yarmoliuk, Andrii A. Kyrylchuk, Oleksandr O. Grygorenko
Summary: Efficient approaches for the synthesis of fluorinated pyrazoles and pyrimidines with saturated (hetero)cyclic substituents were described. The methods rely on heterocyclizations using sp(3)-enriched beta-bromo-alpha,alpha-difluoroketones and fluorinated enaminones derived from saturated heterocyclic alpha-fluoroketones. These compounds serve as useful synthetic intermediates and meet the lead-oriented synthesis criteria.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dake Song, Yi Qin, Ying Liu, Jifan Wang, Haijie Yang, Zhonghui Zheng, Feng Xu, Xuefei Bao, Guoliang Chen
Summary: The immobilization of ciprofloxacin on chloromethyl polystyrene resin as a recyclable ligand for copper-catalyzed coupling reactions of (hetero)aryl halides and amines provides excellent results. The ligand is easily recovered and reused without loss of catalytic ability, and is environmentally friendly with no detectable ciprofloxacin in the reaction solution. Important structural units for the pharmaceutical and chemical industries can be assembled using this method.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Organic
Vincent O. Hervin, Eloi P. Coutant, Glwadys Gagnot, Yves L. Janin
SYNTHESIS-STUTTGART
(2017)
Article
Oncology
Stephanie Arnould, Genevieve Rodier, Gisele Matar, Charles Vincent, Nelly Pirot, Yoann Delorme, Charlene Berthet, Yoan Buscail, Jean Yohan Noel, Simon Lachambre, Marta Jarlier, Florence Bernex, Helene Delpech, Pierre Olivier Vidalain, Yves L. Janin, Charles Theillet, Claude Sardet
Article
Chemistry, Organic
Eloi P. Coutant, Vincent Hervin, Glwadys Gagnot, Candice Ford, Racha Baatallah, Yves L. Janin
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Glwadys Gagnot, Vincent Hervin, Eloi P. Coutant, Sarah Desmons, Racha Baatallah, Victor Monnot, Yves L. Janin
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Eloi P. Coutant, Glwadys Gagnot, Vincent Hervin, Racha Baatallah, Sophie Goyard, Yves Jacob, Thierry Rosek, Yves L. Janin
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Multidisciplinary Sciences
Soon Gang Choi, Julien Olivet, Patricia Cassonnet, Pierre-Olivier Vidalain, Katja Lucks, Luke Lambourne, Kerstin Spirohn, Irma Lemmens, Melanie Dos Santos, Caroline Demeret, Louis Jones, Sudharshan Rangarajan, Wenting Bian, Eloi P. Coutant, Yves L. Janin, Sylvie van Der Werf, Philipp Trepte, Erich E. Wanke, Javier De Las Rivas, Jan Tavernier, Jean-Claude Twizere, Tong Hao, David E. Hill, Marc Vidal, Michael A. Calderwood, Yves Jacob
NATURE COMMUNICATIONS
(2019)
Article
Allergy
Sophie Goyard, Bianca Balbino, Rebecca S. Chinthrajah, Shu-Chen Lyu, Yves L. Janin, Pierre Bruhns, Pascal Poncet, Stephen J. Galli, Kari C. Nadeau, Laurent L. Reber, Thierry Rose
Article
Chemistry, Multidisciplinary
Glwadys Gagnot, Vincent Hervin, Eloi P. Coutant, Sophie Goyard, Yves Jacob, Thierry Rose, Fatima Ezzahra Hibti, Alessia Quatela, Yves L. Janin
Summary: This work focuses on the design and synthesis of luciferin analogues related to blue-hued coelenterazine, aiming to produce photons possibly at different wavelengths. Despite the presence of substituents found in actual substrates, no bioluminescence was observed with these compounds, however, they produced light signals through chemiluminescence in a phosphate buffer. The addition of a quaternary ammonium salt in the buffer increased the light signal intensity, contributing to the determination of emission spectra of these luciferin analogues.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Immunology
Francois Anna, Sophie Goyard, Ana Ines Lalanne, Fabien Nevo, Marion Gransagne, Philippe Souque, Delphine Louis, Veronique Gillon, Isabelle Turbiez, Francois-Clement Bidard, Aline Gobillion, Alexia Savignoni, Maude Guillot-Delost, Francois Dejardin, Evelyne Dufour, Stephane Petres, Odile Richard-Le Goff, Zaineb Choucha, Olivier Helynck, Yves L. Janin, Nicolas Escriou, Pierre Charneau, Franck Perez, Thierry Rose, Olivier Lantz
Summary: This study conducted in Paris conurbation found that the prevalence of SARS-CoV-2 infection in active workers was approximately 11.6% in May-July 2020, higher than laboratory testing positivity rates. The research also indicated that some infected individuals did not exhibit systemic IgG responses, suggesting that the true infection rate may have reached 16.6%, with anosmia and ageusia being common symptoms of infection.
EUROPEAN JOURNAL OF IMMUNOLOGY
(2021)
Article
Multidisciplinary Sciences
Juliette Fernandez, Cedric Hassen-Khodja, Virginie Georget, Thierry Rose, Yves Jacob, Yves L. Janin, Sebastien Nisole, Pierre-Olivier Vidalain, Nathalie J. Arhel
Summary: The recent emergence and reemergence of viruses in the human population has emphasized the necessity of developing broader panels of therapeutic molecules. High-throughput screening assays can identify innovative antiviral molecules by providing access to untargeted steps of the viral replication cycle. The development of an innovative protein complementation assay, named alpha Centauri, allows for the measurement of viral translocation between subcellular compartments, offering a robust readout of specific steps of viral infection in a multiwell format suitable for high-throughput screening.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Organic
Glwadys Gagnot, Pierre Legrand, Amira Tadros, Fatima Ezzahra Hibti, Alessia Quatela, Yves L. Janin
Summary: Research on new chemiluminescent substances related to marine luciferin coelenterazine led to the synthesis of nitrogen-rich pyridopyrazine-bearing analogues, including the benzyl-bearing pyridopyrazinols. Challenges were faced in the synthesis of halogenated pyridopyrazines, with varying degrees of difficulties encountered. Despite these challenges, the target O-acetylated luciferin and its derivative were successfully prepared, with their chemiluminescence emission spectra determined.
SYNTHESIS-STUTTGART
(2021)
Article
Virology
Cyrille Mathieu, Franck Touret, Clemence Jacquemin, Yves L. Janin, Antoine Nougairede, Manon Brailly, Magalie Mazelier, Didier Decimo, Virginie Vasseur, Aymeric Hans, Jose-Carlos Valle-Casuso, Xavier de Lamballerie, Branka Horvat, Patrice Andre, Mustapha Si-Tahar, Vincent Lotteau, Pierre-Olivier Vidalain
Summary: The development of a SARS-CoV-2 infection reporting system facilitates the screening of compound libraries to discover new antiviral drugs. The study found that inhibitors of pyrimidine biosynthesis and NADPH oxidase (NOX) inhibitors have inhibitory effects on SARS-CoV-2 replication.
Article
Chemistry, Organic
Pierre Legrand, Yves L. Janin
Summary: This article reports an improved method for the synthesis of 2-hydroxypyrazines, which can enhance the regioselectivity and yield of the product. By using tetraalkylammonium hydroxide as the reaction parameter, starting from phenylglyoxal and alpha-aminoamides, pyrazine-containing new chemical entities of potential interest in medicinal chemistry were obtained.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yves L. Janin
Summary: This perspective paper discusses the challenges medicinal chemists face in drug discovery and emphasizes the importance of academic researchers in addressing these challenges. The paper presents successful examples of drug candidate discoveries and provides suggestions for contributions from academic medicinal chemists. It highlights the need for increased funding support for academic research in drug development.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Eloi P. Coutant, Sophie Goyard, Vincent Hervin, Glwadys Gagnot, Racha Baatallah, Yves Jacob, Thierry Rose, Yves L. Janin
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)