Article
Chemistry, Organic
Yusuke Tomita, Naoto Haraguchi, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
Summary: A traditional cobalt catalyst system has been found to exhibit previously undiscovered reactivity. Depending on the choice of tertiary phosphines and substrates, this catalytic system can catalyze diverse cycloadditions, yielding various cyclic compounds. The bite angles of the ligands used significantly contribute to the catalytic diversity.
Article
Chemistry, Medicinal
Annie R. Hooper, Alexander S. Burns
Summary: In this study, a masking strategy using acrylamides is reported, allowing the introduction of masked functionality early in a synthetic route and specific thermal deprotection. The stability of acrylamide adducts is influenced by solvent and structural factors, as determined through kinetic studies. This protection strategy improves the yield of base-promoted reactions.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Qiuyu He, Lirong Cao, Yiran Wei, Gregory R. Dake
Summary: The utility of 2-diphenylphosphoryloxy-1,3-dienes for constructing substituted nitrogen heterocycles is demonstrated. These dienes undergo boron trifluoride-promoted aza-Diels-Alder reactions with imines or related species formed in situ using aldehydes and amine derivatives. The stability of the dienes allows for a three-component reaction without the need for special precautions. The enol phosphate functional group is highlighted for further reactions, generating functionalized piperidenes or pyridines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Polymer Science
Daniela Ionita, Mariana Cristea, Constantin Gaina, Mihaela Silion, Bogdan C. Simionescu
Summary: This study reveals the retroDA reaction of anthracene-maleimide Diels-Alder adduct in anthracene modified polyester resins through thermal analysis. At high temperatures, maleimide homopolymerizes and reacts with allyl groups, resulting in the absence of thermal DA reaction.
Article
Chemistry, Organic
Casper Larsen Barlose, Jonas Faghtmann, Rene Slot Bitsch, Joseph Daniel Gbubele, Karl Anker Jorgensen
Summary: The combination of asymmetric organocatalysis with the (pseudo)-halogen effect allows for the efficient formation of chiral norcarane scaffolds. These scaffolds can easily undergo rearrangements or lactonization to form intricate chiral ring structures.
Review
Biochemistry & Molecular Biology
Ignacio E. Tobal, Rocio Bautista, David Diez, Narciso M. Garrido, Pilar Garcia-Garcia
Summary: Building blocks play a crucial role in synthetic organic chemistry, with the Diels-Alder cycloaddition reaction being a common application. Cyclic dienes are important for facilitating this reaction. By utilizing cyclic dienes with unique characteristics, biologically active compounds with interesting properties can be synthesized.
Article
Chemistry, Organic
Rafael G. Uceda, Esther Roldan-Molina, Jorge A. R. Navarro, J. Enrique Oltra
Summary: This study explores the use of electron-deficient dienes as substrates in the aza Diels-Alder reaction, showing that the amide group significantly influences the yield of the reaction products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Byounghyun Kim, Juhyen Lee, Han Yong Bae, Seung Uk Son, Changsik Song
Summary: A facile synthetic pathway for phthalimide derivatives from biomass-derived furan has been developed in this study, which can generate phthalimides with unique properties such as supramolecular gels formation and sensing abilities for anions.
MACROMOLECULAR RAPID COMMUNICATIONS
(2023)
Article
Materials Science, Multidisciplinary
Kai-Cheng Zhong, Jyh-Chien Chen, Shih-Wei Lee, Hsin-Chung Wu
Summary: In this study, two alicyclic dianhydrides with methyl substituents were synthesized and used to prepare high-performance polyimides for flexible electronic applications. The introduction of methyl substituents enhanced the properties of the polyimides, which formed flexible, transparent, and colorless films with superior optical transmittance and high thermal stability. These polyimides also showed excellent solubility in organic solvents, indicating potential applications as negative photosensitive polyimides.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Xin-Qi Zhu, Qian Wang, Jieping Zhu
Summary: This study reports chiral phosphoric acid-catalyzed enantioselective Diels-Alder reactions and three-component reactions, which can efficiently synthesize compounds with multiple functional groups in high yields and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Samuel Lauzon, Lionel Schouwey, Thierry Ollevier
Summary: A chiral ligand was successfully synthesized and its structure and configuration were determined by single-crystal diffraction analysis. The newly synthesized ligand displayed excellent catalytic activity and selectivity in iron-catalyzed asymmetric reactions.
Article
Biochemistry & Molecular Biology
Hongliang Wei, Songmao Li, Zijun Liu, Hongli Chen, Yuhua Liu, Weikun Li, Gang Wang
Summary: Starch-cellulose interpenetrating network (IPN) hydrogels were prepared via sequential Diels-Alder click reaction and photopolymerization, with the addition of beta-cyclodextrin to improve performance. The sustained release behavior of drug-loaded hydrogels was studied using 5-fluorouracil as a model drug. The strategy shows potential for applications in preparing IPN hydrogels due to the controllable photopolymerization and catalyst-free Diels-Alder reaction.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Chemistry, Physical
Lilia Hassouna, Sachin Kumar Enganati, Florence Bally-Le Gall, Gregory Mertz, Jerome Bour, David Ruch, Vincent Roucoules
Summary: The study explored the use of TOF-SIMS for monitoring the interfacial retro Diels-Alder reaction on SAMs by detecting released molecular fragments. By tracking the decay of the fragment's peak integral, the reaction conversion could be determined. The viability of this method was discussed in comparison with results obtained from H-1 NMR spectroscopy.
Article
Chemistry, Organic
Elisa Brambilla, Sara Leoni, Giorgio Abbiati, Valentina Pirovano, Elisabetta Rossi
Summary: Spiroindolenines were used as cyclic imine substrates in formal aza-Diels-Alder reactions with Danishefsky's diene or silyloxy-substituted electron-rich dienes, leading to the synthesis of tetrahydropyrido[1,2-a]spiroindolinones under mild conditions in the presence of ytterbium triflate as a Lewis acidic catalyst, with good yields. The reaction results in the preparation of a small library of a new class of conformational constrained heterocyclic derivatives that easily undergo selective and efficient manipulations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Savva A. Ponomarev, Roman Larkovich, Alexander S. Aldoshin, Andrey A. Tabolin, Sema L. Ioffe, Jonathan Gross, Till Opatz, Valentine G. Nenajdenko
Summary: The Diels-Alder reaction of beta-fluoro-beta-nitrostyrenes with cyclic 1,3-dienes was studied, leading to the synthesis of a series of novel monofluorinated norbornenes with yields up to 97%. Activation parameters were calculated using kinetic data from reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene, demonstrating the synthetic utility of the cycloadducts obtained.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Raquel Diana-Rivero, Beate Halsvik, Fernando Garcia Tellado, David Tejedor
Summary: A simple and metal-free domino methodology was used to synthesize various 2-aminopyrroles from alkynyl vinyl hydrazides, involving a novel rearrangement and cyclization reaction. This approach allowed the preparation of 2-amino-pyrroles with diverse substituents.
Article
Virology
Rajkumar Lalji Sahani, Raquel Diana-Rivero, Sanjeev Kumar V. Vernekar, Lei Wang, Haijuan Du, Huanchun Zhang, Andres Emanuelli Castaner, Mary C. Casey, Karen A. Kirby, Philip R. Tedbury, Jiashu Xie, Stefan G. Sarafianos, Zhengqiang Wang
Summary: Research on multiple PF74 analogs demonstrated that two series of compounds replacing the phenylalanine carboxamide moiety have potential as candidates. Metabolic stability assays also indicated that blocking the C5 position of the indole ring could enhance resistance to oxidative metabolism.
Article
Biochemistry & Molecular Biology
Samuel Delgado-Hernandez, Fernando Garcia-Tellado, David Tejedor
Summary: A novel organocatalytic multicomponent cyanovinylation reaction has been developed for the synthesis of conjugated cyanomethyl vinyl ethers, delivering excellent yields and predominance of the E-isomer. The reaction shows high tolerance to the structure and composition of aldehydes, and features instrumentally simple, cost-effective, environmentally friendly, and sustainable benefits.
Article
Chemistry, Medicinal
Carlos Bethencourt-Estrella, Samuel Delgado-Hernandez, Atteneri Lopez-Arencibia, Desiree San Nicolas-Hernandez, Ines Sifaoui, David Tejedor, Fernando Garcia-Tellado, Jacob Lorenzo-Morales, Jose Pinero
Summary: Chagas disease, caused by the protozoan parasite Trypanosoma cruzi, is a neglected infection that leads to over 7000 deaths annually, with limited therapy options available. A study has shown that novel acrylonitriles have potential as new trypanocidal agents for the treatment of Chagas disease.
Article
Parasitology
Aitor Rizo-Liendo, Inigo Arberas-Jimenez, Ines Sifaoui, Dimitra Gkolfi, Yiset Santana, Leandro Cotos, David Tejedor, Fernando Garcia-Tellado, Jose E. Pinero, Jacob Lorenzo-Morales
Summary: The study evaluated the activity of 14 novel isobenzofuranones against the pathogenic amoeba Naegleria fowleri, with some compounds showing the ability to eliminate trophozoites and induce programmed cell death. These tested compounds could potentially serve as therapeutic candidates for the treatment of Primary Amoebic Encephalitis.
INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE
(2021)
Article
Medicine, Research & Experimental
Ruben L. Rodriguez-Exposito, Maria Reyes-Batlle, Ines Sifaoui, David Tejedor, Fernando Garcia-Tellado, Jose E. Pinero, Jacob Lorenzo-Morales
Summary: This study assessed the IC50 of isobenzofuranone derivatives against Acanthamoeba strains and identified two active derivatives with low IC50. Additionally, the study showed that both compounds triggered programmed cell death in Acanthamoeba strains.
BIOMEDICINE & PHARMACOTHERAPY
(2022)
Article
Biochemistry & Molecular Biology
Carlos J. Bethencourt-Estrella, Samuel Delgado-Hernandez, Atteneri Lopez-Arencibia, Desiree San Nicolas-Hernandez, David Tejedor, Fernando Garcia-Tellado, Jacob Lorenzo-Morales, Jose E. Pinero
Summary: Leishmaniasis is one of the most important tropical diseases, with approximately one million new cases each year. Current treatments are not fully effective and are toxic, so there is a need to develop new therapies that are more effective and less toxic. This study found that certain acrylonitrile derivatives have good selectivity in killing Leishmania parasites and induce programmed cell death.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tanausu Santos, Yaiza Perez-Perez, David S. Rivero, Raquel Diana-Rivero, Fernando Garcia-Tellado, David Tejedor, Romen Carrillo
Summary: Dynamic Covalent Chemistry (DCvC) plays an increasingly important role in supramolecular chemistry and materials science. In this study, we demonstrate the dynamic nature of the exchange between phenols and vinyl ethers. The fast exchange at room temperature and under mild conditions has been observed. The equilibrium constants and electronic effects of phenol substituents have been calculated. This novel incorporation into the DCvC toolbox holds great potential and has been successfully applied in the synthesis of a responsive molecular cage.
Article
Biochemistry & Molecular Biology
Javier Chao-Pellicer, Inigo Arberas-Jimenez, Samuel Delgado-Hernandez, Ines Sifaoui, David Tejedor, Fernando Garcia-Tellado, Jose E. Pinero, Jacob Lorenzo-Morales
Summary: This article discusses the research on primary amoebic meningoencephalitis (PAM) caused by the pathogenic amoeba Naegleria fowleri, as well as the treatment methods. The study found that QOET-51, QOET-59, QOET-64, QOET-67, QOET-72, QOET-77, and QOET-79 among the 46 synthesized compounds were the most effective molecules. Additionally, the study investigated the mechanism of action of these compounds.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Parasitology
Carlos J. Bethencourt-Estrella, Samuel Delgado-Hernandez, Atteneri Lopez-Arencibia, Desiree San Nicolas-Hernandez, David Tejedor, Fernando Garcia-Tellado, Jacob Lorenzo-Morales, Jose E. Pinero
Summary: Chagas disease is a serious illness that can cause megacolon, heart disease, and even death. Current therapies for this disease are outdated and have significant side effects. Therefore, there is a need to search for new compounds that are safer, less toxic, and more effective against the parasite. This study investigated the antichagasic activity of 46 novel cyanomethyl vinyl ether derivatives and identified four compounds that showed selective activity and triggered programmed cell death in the parasites, making them potential candidates for future Chagas disease therapeutics.
INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE
(2023)
