Article
Chemistry, Multidisciplinary
Samuel Nees, Tim Wellnitz, Fabian Dankert, Marcel Haerterich, Simon Dotzauer, Milica Feldt, Holger Braunschweig, Christian Hering-Junghans
Summary: Heterocycles containing group 13 and 15 elements play important roles in organic, biomedical, and materials chemistry. However, heterocycles containing P and Al elements are rare. In this study, phosphaalumenes were used to react with alkynes, alkenes, and conjugated double bond systems. Different types of heterocycles, including phosphaalumetes, phosphaaluminabarrelenes, and aluminaphosphorinanes, were synthesized. Experimental work, along with theoretical studies, provided insights into the mechanism of these heterocycle formations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Jing Huang, Bo Jiang, Xiyuan Zhang, Yanfeng Gao, Xiufang Xu, Zhiwei Miao
Summary: A synthetic strategy for accessing functionalized azabicyclo[3.3.1]alkenones with three tertiary stereocenters has been developed. The method is scalable and the products can be transformed to various eight-membered-ring bridged heterocyclic molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Physical
Tong-De Tan, Ze-Shu Wang, Peng-Cheng Qian, Long-Wu Ye
Summary: Ynamides, as electron-rich heteroatom-substituted alkynes, have proven to be versatile reagents for organic synthesis and have received extensive attention. Radical reactions of ynamides, categorized by radical attack at the alpha-position and beta-position, are reviewed in this article to highlight reaction selectivity, scope, mechanism, and applicability. The aim is to provide a comprehensive summarization of these advances to guide the further development of ynamide chemistry.
Article
Chemistry, Multidisciplinary
Jackson S. Henneveld, Farshad Shiri, Alireza Ariafard, Nigel T. Lucas, Alex C. Bissember, Bill C. Hawkins
Summary: The investigation and formalization of the distinctive dipole-transmissive dipolar cycloaddition (DTDC) methodology is reported. A DTDC procedure was developed by taking advantage of the structural complementarity of azide and diazoalkane 1,3-dipoles. This method allows for the rapid construction of functionalized polycyclic N-heterocycles through intramolecular azide-alkene 1,3-dipolar cycloadditions followed by N-derivatization and subsequent 1,3-dipolar cycloadditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Gabrielle E. Cabrera, Tristen A. Reid, Eric C. Johnson, Joshua A. Orlicki, Noah Z. Burns, Jesse J. Sabatini
Summary: The synthesis of a new isoxazole compound and its potential in energy applications are discussed in this article. The compound shows high density and superior propulsion performance, making it a potential plasticizer for future gun and rocket propellants.
Article
Chemistry, Organic
Akira Nakamura, Tohko Kine, Haruna Uenishi, Yuri Maki, Yasuhito Kase, Mayo Takagi, Tomohiro Maegawa
Summary: A regioselective synthesis of 3,4-disubstituted isoxazoles has been developed using a chalcone-rearrangement strategy. The reaction of beta-ketoacetals with hydroxylamine hydrochloride and pyridine resulted in the formation of the corresponding 3,4-disubstituted isoxazoles via isoxazolines or oximes. Depending on the substrate, another disubstituted isomer was also obtained under optimized conditions, and a reaction mechanism is proposed for each transformation.
Article
Chemistry, Multidisciplinary
Matthieu J. R. Richter, Frederic J. Zecri, Karin Briner, Stuart L. Schreiber
Summary: In this study, a novel and efficient synthesis method for cyclopropane-fused lactams was developed using specific chemical agents. The method demonstrated broad applicability and modularity, allowing for the synthesis of structurally diverse complex molecular scaffolds. The utility of this method was further highlighted through the concise synthesis of two therapeutic agents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Tsai-Hui Lung, Yi-Ru Chen, Chen-Ling Chang, Wey-Chyng Jeng, Pei-Shan Wu, Sandip Sambhaji Vagh, Gangababu Marri, Yi-Fang Lin, Wenwei Lin
Summary: A catalyst-controlled diversity-oriented synthesis of spirohydroquinoline-indandiones and 3-methylenehydroquinoline-indandiones was reported using ortho-sulfonamidophenyl-substituted para-quinone methides and allylidene-indandiones. Organobases such as DMAP or TMG were utilized to selectively control the reaction pathway, resulting in products with yields of 40-99% and excellent diastereoselectivities. Mechanistic studies revealed that spirohydroquinoline-indandione was the kinetic product, which underwent an unusual base-initiated 1,3-nitrogen rearrangement process to afford 3-methylenehydroquinoline-indandione in the presence of TMG.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Shan-Shan Zhu, Heng Li, Rong Fu, Wen-Juan Hao, Shu-Liang Wang, Shu-Jiang Tu, Bo Jiang
Summary: The Lewis acid-catalyzed tricyclization method enables the efficient synthesis of rotationally hindered tribenzo[a,c,j]xanthenes, allowing scission/recombination of C-C triple bonds with good stereoselectivity and substituent compatibility.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Organic
Suchithra Madhavan, Santosh Kumar Keshri, Manmohan Kapur
Summary: This review focuses on transition metal-mediated functionalization of isoxazoles, including using isoxazoles as directing groups for TM-catalyzed C-H functionalization reactions, TM-catalyzed direct C-H functionalization, cross-coupling reactions of isoxazoles, TM-catalyzed annulation reactions of isoxazoles, and ring-opening reactions of isoxazoles under TM-catalysis. It provides insights on reaction designs, advantages and limitations, mechanistic details, and challenges to inspire synthetic organic and medicinal chemists to explore new reaction arenas and utilize the isoxazole scaffold.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Marcos Diaz-Fernandez, Saturnino Calvo-Losada, J. -Joaquin Quirante, Francisco Sarabia, Manuel Algarra, M. -Soledad Pino-Gonzalez
Summary: This review summarizes synthetic advances in the formation of pyrimidine and related heterocyclic compounds from 2010 to mid-2022. It focuses on different types of cycloadditions that lead to the formation of the pyrimidine ring, considering the number of components involved. A separate review on the Biginelli reaction and related reactions will be conducted in the future.
Article
Chemistry, Organic
Shuangping Huang, Jing Ma, Yikun Yi, Mingtao Li, Ping Cai, Na Wu
Summary: In this study, a catalyst-free metal-free [2 + 2] cycloaddition-retro-electrocyclisation (CA-RE) reaction was reported, which provided electron-push-pull light-harvesting small molecules by reacting arylynamines with tetracyanoquinodimethane. The reactivity of arylynamines was balanced properly to achieve high selectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Victor Laina-Martin, Jose A. Fernandez-Salas, Jose Aleman
Summary: Cycloaddition reactions, particularly Diels-Alder reactions, are regarded as powerful methodologies for building carbon-carbon bonds. The inverse-electron-demand hetero-Diels-Alder reactions have been a significant breakthrough for synthesizing heterocyclic compounds. Among them, the organocatalytic enantioselective version has been extensively studied due to its asymmetric construction of diversely functionalized scaffolds under green chemistry conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Jiaxin Liu, Yin Wei, Min Shi
Summary: A new method for the direct single-electron oxidation of methylenecyclopropanes (MCPs) was reported, leading to the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives through merging visible light photoredox catalysis and cobalt catalysis. In MeCN with Et3N·3HF, fluorinated derivatives were obtained in moderate yields, while in MeCN/HFIP, good yields were achieved through a MHAT process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Susheel Gulati, Rajvir Singh, Suman Sangwan
Summary: The application of green chemistry in the synthesis of potential bioactive heterocyclic compounds has become a key area of research for organic chemists. The development of nonhazardous synthetic protocols has gained particular attention due to environmental concerns. Microbial infections and cancer pose significant threats to humanity, necessitating the design and synthesis of new compounds. Heterocycles play a crucial role in the synthesis of pharmaceuticals and agrochemicals, and their methods of preparation are of great importance in organic synthesis.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Oncology
Raffaella Pacchiana, Nidula Mullappilly, Andrea Pinto, Stefania Bova, Stefania Forciniti, Gregorio Cullia, Elisa Dalla Pozza, Emanuela Bottani, Ilaria Decimo, Ilaria Dando, Stefano Bruno, Paola Conti, Massimo Donadelli
Summary: This study tested the effects of 3-bromo-isoxazoline derivatives on pancreatic ductal-adenocarcinoma cells and found that these compounds inhibited cell proliferation. Two promising compounds were selected for in vivo testing and one of them, AXP-3019, effectively blocked PDAC-cell growth without apparent toxicity. These findings support the idea that targeting the glycolytic pathway, specifically GAPDH, is an effective therapy for pancreatic cancer, and 3-bromo-isoxazoline derivatives represent a new class of anti-cancer compounds.
Article
Biochemistry & Molecular Biology
Christian Carpene, Penelope Viana, Zsuzsa Iffiu-Soltesz, Pal Tapolcsanyi, Anna Agota Foldi, Peter Matyus, Petra Dunkel
Summary: Benzylamine, a natural molecule found in food and edible plants, has been found to activate hexose uptake and inhibit lipolysis in human fat cells. These effects rely on the oxidation of benzylamine by amine oxidases in adipocytes, leading to the production of hydrogen peroxide, which exhibits insulin-like actions. The study identified compounds that interact with highly expressed amine oxidases in human adipocytes and showed that they have similar metabolic effects to benzylamine, making them potential candidates for the treatment of obesity and diabetes.
Article
Biochemistry & Molecular Biology
Desiree Pecora, Francesca Annunziata, Sergio Pegurri, Pasquale Picone, Andrea Pinto, Domenico Nuzzo, Lucia Tamborini
Summary: A series of phenolic derivatives targeting mitochondria were synthesized under flow conditions starting from natural phenolic acids. The two-step continuous flow protocol in the bioavailable solvent Cyrene allowed for the isolation of the MITO compounds with moderate to good yields. The safety of the compounds was evaluated by cell viability analysis, and the non-toxic dose ranged from 3.5 to 125 μM in the human neuronal cell line SH-SH5Y. Two of the synthesized MITO compounds showed interesting performances in protecting mitochondria from oxidative damage.
Article
Biochemistry & Molecular Biology
Cecilia Pinna, Tommaso Laurenzi, Fabio Forlani, Luca Palazzolo, Claire Beatrice Nolan, Michael S. S. Christodoulou, Paolo Cortesi, Andrea Pinto, Ivano Eberini, Andrea Kunova, Sabrina Dallavalle
Summary: The European Farm to Fork strategy requires reducing the use of synthetic pesticides, which exposes vulnerable agricultural sectors like European risiculture to devastating diseases and endangers food security. Therefore, novel scaffolds need to be identified for the synthesis of environmentally friendly fungicides.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Peter Riber Johnsen, Cecilia Pinna, Luce Mattio, Mathilde Bech Strube, Mattia Di Nunzio, Stefania Iametti, Sabrina Dallavalle, Andrea Pinto, Hanne Frokiaer
Summary: This study compares the effects of seven different structural types of stilbenoids on the modulation of cytokine production and antioxidant response. Monomeric compounds showed dose-dependent inhibition of cytokine production induced by E. coli, with resveratrol and piceatannol also inhibiting IL-10 production. All monomers, except trimethoxy-resveratrol, inhibited cytokine production induced by L. acidophilus. However, the dimer dehydro-delta-viniferin remarkably enhanced IL-12 production induced by L. acidophilus.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Biochemistry & Molecular Biology
Michael S. S. Christodoulou, Federica Villa, Andrea Pinto, Francesca Cappitelli
Summary: Biofilms are a multicellular lifestyle of microorganisms found on various surfaces. Using phytochemicals at sub-lethal concentrations has emerged as a promising alternative strategy to control biofilms. Studies have shown that at sub-lethal concentrations, polyphenolic substances disrupt the healthy redox cycle in cells, leading to an accumulation of reactive oxygen species.
Article
Chemistry, Medicinal
Andrea Galbiati, Stefania Bova, Raffaella Pacchiana, Chiara Borsari, Marco Persico, Aureliano Zana, Stefano Bruno, Massimo Donadelli, Caterina Fattorusso, Paola Conti
Summary: Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) plays a crucial role in cancer cell metabolism and is considered a potential target for anticancer drugs. Compound 11, a spirocyclic derivative, was identified as a covalent inhibitor of human GAPDH (hGAPDH) with higher reactivity than other known inhibitors. Computational studies confirmed the importance of conformational rigidification for stabilizing the interaction between the inhibitor and the binding site. Compound 11 selectively reacted with the activated cysteine of hGAPDH and inhibited cancer cell growth. These findings suggest that compound 11 has potential for the development of anticancer agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Andrea Galbiati, Aureliano Zana, Chiara Borsari, Marco Persico, Stefania Bova, Oleh Tkachuk, Alexandra Ioana Corfu, Lucia Tamborini, Nicoletta Basilico, Caterina Fattorusso, Stefano Bruno, Silvia Parapini, Paola Conti
Summary: This study investigated the significance of chirality for the natural compound 3-Br-acivicin (3-BA) and its derivatives. The (5S, aS) isomers displayed significant antiplasmodial activity, suggesting their uptake might be mediated by the L-amino acid transport system. Stereochemistry only affected target binding for two subclasses, but led to significant differences in antimalarial activity for all subclasses, indicating that stereoselective uptake might be responsible for the enhanced activity of (5S, aS) isomers.
Article
Chemistry, Multidisciplinary
Sara Vicinanza, Francesca Annunziata, Desiree Pecora, Andrea Pinto, Lucia Tamborini
Summary: A facile and convenient lipase-catalyzed flow approach has been developed for synthesizing tyrosol and hydroxytyrosol methyl carbonates in neat dimethylcarbonate, with quantitative yield and high catalyst productivity. The biocatalytic approach can also be used for preparing value-added symmetrical tyrosol and hydroxytyrosol carbonates.
Article
Chemistry, Physical
Agostina Colacicco, Giorgia Catinella, Cecilia Pinna, Alessandro Pellis, Stefano Farris, Lucia Tamborini, Sabrina Dallavalle, Francesco Molinari, Martina Letizia Contente, Andrea Pinto
Summary: An efficient one-pot, 2-step flow bioprocess has been developed for obtaining the aglycones of hesperidin (HES) and rutin (RT). The strategy involves co-immobilizing commercially available α-rhamnosidase and extremophilic β-glycosidase on glyoxyl-agarose beads to create a high-performing multi-active biocatalyst. By optimizing the reaction conditions and implementing a flow switch, the process achieves high productivity, cost-efficiency, and sustainability.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Organic
Attila Csomos, Orsolya Pantl, Petra Dunkel, Dora Bogdan, Arnold Steckel, Gitta Schlosser, Zoltan Mucsi, Ervin Kovacs
Summary: 8-Aminoquinoline-2-carbaldehydes are useful building blocks for ion sensors, and a general method for their preparation starting from commercially available 8-bromo-2-methylquinoline is presented. Different sidechains were introduced to fine-tune their affinity and selectivity, and an alternative method is proposed to overcome the limitation of high catalyst affinity.
