Article
Chemistry, Analytical
Asaad S. Mohamed, Osama M. Habib, Nouria A. Al-Awadi
Summary: Flash vacuum pyrolysis of various aryl propargyl ethers with different substituents was investigated, and mechanisms for some reactions were proposed.
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS
(2022)
Article
Chemistry, Organic
Chih-Hao Luo, Pei-Ling Wang, Che-Chien Chang
Summary: Various N-(2-bromo-allyl) benzamides were used as starting materials for studying vinyl radical cyclization reactions, which produced beta-aryl-gamma-lactams without affecting the carbonyl group. The cascade radical reaction led to the synthesis of alpha,beta-unsaturated-beta-aryl-gamma-lactam derivatives, with the effects of substituents on the amino and aryl groups examined.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Danielle L. McConnell, Alisha M. Blades, Danielle Gomes Rodrigues, Phoebe Keyes, Justin C. Sonberg, Caitlin E. Anthony, Sofia Rachad, Olivia M. Simone, Caroline F. Sullivan, Jonathan D. Shapiro, Christopher C. Williams, Benjamin C. Schafer, Amy M. Glanzer, Holly L. Hutchinson, Ashley B. Thayaparan, Zoe A. Krevlin, Isabella C. Bote, Yasin A. Haffary, Sambat Bhandari, Jack A. Goodman, Max M. Majireck
Summary: In this report, a general synthetic approach to bench-stable N-quaternized ketene N,O-acetals was described. These compounds can be used as reagents or synthetic intermediates in multiple reaction types, showing a broad potential in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Rudolfs Belaunieks, Mikus Purins, Rebeka Anna Lipina, Anatoly Mishnev, Maris Turks
Summary: This study focuses on the activation of terminal alkynes with a silyl group and the synthesis of stereochemically defined allyl ethers and esters through 1,2-silyl group migration and interception reactions with external nucleophiles. The obtained products can serve as building blocks for further functionalization reactions.
Article
Chemistry, Organic
Antonia Rinaldi, Vittoria Lange, Dina Scarpi, Ernesto G. Occhiato
Summary: In this study, the synthesis of (+/-)-epi-jungianol was successfully achieved through a gold(I)-catalyzed propargyl Claisen rearrangement/hydroarylation cascade reaction of suitably substituted propargyl vinyl ethers. Two different routes were compared, with the one involving substrates with less substitution on the vinyl moiety providing a higher overall yield despite requiring two additional steps. Additionally, a method for preparing acid-sensitive propargyl vinyl ethers with an alpha-alkyl-substituted vinyl moiety and their reactivity under gold catalysis was reported.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wen-Bin Huang, Li-Qi Qiu, Fang-Yu Ren, Liang-Nian He
Summary: The study introduces a straightforward method for the synthesis of alpha-amino phosphine oxides via three-component reactions. The use of aryne to activate formamide simplifies the procedure and offers high efficiency under mild conditions. The mechanistic perception suggests a cascade sequence involving formal [2 + 2] cycloaddition and 1,4-addition reactions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Xiao Dong, Qi Yukki Li, Tehshik P. Yoon
Summary: The research shows that in designing photochemical reactions, not only the excited-state oxidation potential is important, but also the oxidation and reduction potentials of the photocatalyst are crucial for the reaction outcome. This highlights the importance of holistic considerations in designing photochemical reactions.
Article
Chemistry, Organic
Yong-Wang Huo, Xinxin Qi, Xiao-Feng Wu
Summary: This study developed a new method for synthesizing alpha,beta-unsaturated thioesters via nickel-catalyzed thiocarbonylation reaction of vinyl triflates with arylsulfonyl chlorides. By using Mo(CO)(6) as both CO source and reductant, alpha,beta-unsaturated thioesters were obtained in moderate to good yields with excellent functional group compatibility. It is notable that this is the first example of nickel-catalyzed carbonylative synthesis of alpha,beta-unsaturated thioesters using arylsulfonyl chlorides as the coupling partner.
Article
Chemistry, Organic
Avishek Ghatak, Amit Pramanik, Asit Kumar Das, Sanjay Bhar
Summary: This study presents an efficient protocol for the solvent-free synthesis of highly substituted propargyl ethers and amines using alumina-sulfuric acid as a recyclable heterogeneous solid acid catalyst. The mild protocol tolerates acid-sensitive moieties and is applicable to a diverse range of alcohols and amines with various substitution patterns. The process is highly atom-efficient, resulting in water as the sole by-product.
Article
Chemistry, Organic
Dorian Dupommier, Michel Boisbrun, Gerald Monard, Corinne Comoy
Summary: By exploring a method for the functionalization of BTZD scaffold, we have opened up a new chemical space around BTZD. Key intermediates, 6-chloro- and 6-formyl BTZD, were obtained and used in Pd catalyzed cross-coupling or Wittig olefination reactions. Various substituents were successfully introduced onto the vinylic position of BTZD, and the stereochemistry of benzylidene derivatives was elucidated through a combined DFT/NMR study.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Timothy J. Paris, Chris Schwartz, Eric Sundall, Rachel Willand-Charnley
Summary: A rapid one-step synthesis of alpha-ketoacetals was achieved via electrophilic etherification, obtaining different yields of products using specific substrates and peroxyacetals. The method is applicable for C-O bond formation at tertiary carbons, with the alpha-OCH3 group playing a critical role in ensuring product formation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Brian Spiegelberg, Haijun Jiao, Reni Grauke, Christoph Kubis, Anke Spannenberg, Adrian Brandt, Andreas Taden, Horst Beck, Sergey Tin, Johannes G. Vries
Summary: The study achieved the iridium-catalyzed transfer vinylation of bio-based polyols and other alcohols and phenols using vinyl acetate in a green solvent. The optimized synthetic procedure demonstrated high selectivity by suppressing side reactions efficiently, leading to the formation of bis-vinyl ethers.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Takahiro Yamada, Yoshimitsu Hashimoto, Kosaku Tanaka, Nobuyoshi Morita, Osamu Tamura
Summary: An efficient method for synthesizing multisubstituted pyridines from beta-aryl-substituted alpha,beta-unsaturated oxime ethers and alkenes via Pd-catalyzed C-H activation has been developed. Systematic optimization of catalyst ligands revealed that sterically hindered pyridines increased reactivity. Mechanistic studies suggested that the products are formed through Pd-catalyzed beta-alkenylation of alpha,beta-unsaturated oxime followed by aza-6 pi-electrocyclization, showcasing the utility of this methodology.
Article
Chemistry, Organic
Narihito Ogawa, Chihiro Uematsu, Yuichi Kobayashi
Summary: This paper describes a stereoselective synthesis of (-)-heliannuol E through intramolecular cyclization of a phenol mesylate, with the introduction of the aromatic group achieved by alpha-selective propargyl substitution of a propargylic phosphate.
Article
Chemistry, Multidisciplinary
Wei Wen, Zhao-Pin Ai, Chang-Lin Yang, Chao-Xing Li, Zhu-Lian Wu, Tian Cai, Qi-Xiang Guo
Summary: This study presents a new catalytic asymmetric approach for the synthesis of chiral alpha-amino ketones using a chiral palladium-catalyzed arylation reaction. The method offers a straightforward and highly stereocontrolled approach for the synthesis of acyclic alpha-amino ketones.
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
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
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
Mariana Ingold, Victoria de la Sovera, Rosina Dapueto, Paola Hernandez, Williams Porcal, Gloria Lopez
Summary: This study focuses on the development of nitric oxide-releasing molecules for the treatment of prostate and bladder cancers. Through multicomponent reactions, a collection of compounds with antiproliferative activity against both cancer cell lines was synthesized. These compounds have potential as lead compounds for the treatment of bladder cancer.
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
Chemistry, Multidisciplinary
Federico Ortiz, Tiago Tassano, Mariana Ingold, Victoria de la Sovera, Adrian Puerta, Jose M. Padron, Gloria Lopez, Williams Porcal
Summary: This article presents a strategy for the rapid and efficient synthesis of nitrovinylfurans, and evaluates the antiproliferative activity of the synthesized compounds. The study found that these newly synthesized compounds exhibited growth inhibition on various cancer cell lines, with low toxicity on normal human cells.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2022)
Article
Biochemistry & Molecular Biology
Maria Varela, Miriam Lopez, Mariana Ingold, Diego Alem, Valentina Perini, Karen Perelmuter, Mariela Bollati-Fogolin, Gloria V. Lopez, Paola Hernandez
Summary: This study evaluated three nitric oxide-releasing compounds as potential therapies for bladder cancer. The results showed that compounds 1 and 3 inhibited the proliferation of bladder cancer cells through DNA damage and downregulation of Survivin. Compound 3 also reduced the migration of bladder cancer cells.
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)
Article
Clinical Neurology
Sofia Ibarburu, Mariangeles Kovacs, Valentina Varela, Jorge Rodriguez-Duarte, Mariana Ingold, Paulina Invernizzi, Williams Porcal, Ana Paula Arevalo, Karen Perelmuter, Mariela Bollati-Fogolin, Carlos Escande, Gloria V. Lopez, Peter King, Ying Si, Yuri Kwon, Carlos Batthyany, Luis Barbeito, Emiliano Trias
Summary: These findings indicate a potential therapeutic effect of BANA in ALS patients, as it can slow down paralysis progression by inhibiting microglial NF-kappa B activation. Experimental results demonstrate that administration of BANA to SOD1(G93A) rats after paralysis onset can improve spinal motor neuron pathology and preserve neuromuscular junction innervation, thus prolonging post-paralysis survival.
