Article
Chemistry, Inorganic & Nuclear
Adam J. Wright, Fiona J. McMartin, Liam G. Dyer, Lloyd H. Sayer, Philip C. Bulman Page, G. Richard Stephenson
Summary: A new copper-catalyzed desymmetrisation reaction has been successfully achieved, leading to the asymmetric synthesis of planar chiral pseudo-isocoumarins with high enantiomeric excess and yield. Tri-functionalized planar chiral ferrocenes are synthesized in a straightforward manner without the need for traditional directing group chemistry.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaofeng Li, Pingping He, Peng Zhu, Yinhong Tang, Yungui Peng
Summary: A method for desymmetrizing asymmetric ring expansion of 4-substituted cyclohexanones with alpha-diazomethylphosphonates catalyzed by a chiral boron Lewis acid has been developed. The method affords beta-ketophosphonate compounds bearing a stereogenic center at the alpha-position in up to 80% yields, 86% ee, and >20 : 1 dr. The obtained products can be further derivatized, demonstrating the synthetic potential of this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Paul S. Riehl, Alistair D. Richardson, Tatsuhiro Sakamoto, Jolene P. Reid, Corinna S. Schindler
Summary: Enantiodivergence is an important concept in asymmetric catalysis, allowing access to both enantiomers of a product when only one enantiomer of the required chiral ligand is readily available. This study focuses on elucidating the origin of metal-controlled enantioselectivity reversal, showing that specific interactions between the substrate and ligand depend on the ionic radius of the metal catalyst. This research has the potential to enhance our understanding of enantiodivergent transformations and facilitate their future design.
Article
Chemistry, Applied
Ayon Chatterjee, D. H. Sreenivasa Rao, Santosh Kumar Padhi
Summary: "In this study, a one-pot, two-step cascade reaction sequence was developed to convert benzylic alcohols to enantioenriched beta-nitroalcohols. By utilizing specific enzymes, high conversion rates and excellent stereoselectivity were achieved, demonstrating a new method for producing chiral pharmaceutical intermediates."
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Thomas Varlet, Geraldine Masson
Summary: Chiral substituted cyclic amines are important in organic synthesis, with stable and easy to synthesize enamides and dienamides serving as versatile building blocks for the preparation of chiral amines. The exceptional synergy between these synthetic synthons and chiral phosphoric acid catalysts has been successfully utilized to develop formal cycloadditions with high enantioselectivity, allowing access to chiral cyclic amines with varying ring sizes.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Haijun Leng, Qian Zhao, Qing Mao, Shuaijiang Liu, Menglan Luo, Rui Qin, Wei Huang, Gu Zhan
Summary: The N-heterocyclic carbene-catalysed retro-aldol/aldol cascade reaction allows for the synthesis of spirocyclopentaneoxindole products with four consecutive stereocenters. By simply changing reaction solvents, diastereodivergent synthesis can be achieved. Selective provision of four stereoisomers can be achieved by using different combinations of a chiral secondary amine and a solvent.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Qian-Yi Wang, Teng-Fei Liu, Li-Feng Chu, Yun Yao, Chong-Dao Lu
Summary: In the presence of a chiral spiro phosphoric acid catalyst, the asymmetric reaction of disubstituted ketenes with N-H pyrroles occurred to afford enantioenriched C-acylated pyrroles bearing alpha-stereogenic carbon centres. This reaction represents a rare example of catalytic asymmetric reaction of ketenes with carbon-based nucleophiles, with significant research implications.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yan Zhang, Jia-Hui Yang, Ying-Qi Xia, Lin Dong, Fen-Er Chen
Summary: An efficient asymmetric Mannich/cyclization cascade strategy was developed using a copper-based complex to synthesize optically active benzothiazolopyrimidine derivatives from 2-benzothiazolimines and N-acylpyrazoles. The mild cascade process allowed for the construction of structurally diverse products with broad substrate scope, achieving excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 d.r.).
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Jun Wei, Jian Zhang, Jun Kee Cheng, Shao-Hua Xiang, Bin Tan
Summary: A new method for the synthesis of chiral beta-amino amides using ambiphilic ynamides as two-carbon synthons has been established. The method allows for the efficient preparation of beta-amino amides with excellent chemo- and stereo-control, and has been successfully applied to the synthesis of over 100 desired products.
Article
Biochemistry & Molecular Biology
Dong-Hua Xie, Cheng Niu, Da-Ming Du
Summary: In this paper, a new protocol for building a chiral ring-fused chroman skeleton was developed through organocatalytic asymmetric Michael addition/hemiketalization cascade reactions. The reactions provided chiral chroman-fused pyrrolidinediones with high yields and excellent stereoselectivities. A scale-up synthesis was also conducted, and a possible reaction mechanism was proposed.
Article
Chemistry, Applied
Ya Wu, Xinya Bu, Yongqi Ke, Huaming Sun, Jingyao Li, Lu Chen, Wei Cui, Yujian He, Li Wu
Summary: Enantiomers of chiral substances possess different biological activities, making it crucial to explore biochemical processes at the enantiomeric level. This study investigated the DNA polymerase-catalyzed reaction controlled by various types of chiral cobalt complexes and found that the enantiomers exhibited different stereocontrol of bioreactivity, which could be attributed to diverse electrostatic energy induced by the attached metal chelates and discrepancies in Van der Waals interactions between the enantiomer and polymerase catalytic sites.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Katsuhiko Moriyama, Yukari Oka
Summary: This article reports an enantioselective cascade Michael/hemiaminal formation of alpha,beta-unsaturated iminoindoles with aldehydes using a chiral aminomethylpyrrolidine catalyst bearing a strongly electron withdrawing arylsulfonyl group. The reaction yields anti-2-hydroxy-hydro-1H-pyrido[2,3-b]indole (anti-alpha-carbolinol) derivatives in high yields with high stereoselectivity. DFT calculation studies reveal the importance of multiple hydrogen-bonding interactions in the reaction, and the reaction product can undergo various transformations.
Article
Chemistry, Applied
Yong Tang, Kaihong Liu, Ye Wu, Siyu Zhou, Tanyu Cheng, Guohua Liu
Summary: The development of cooperative catalysis is important for multi-step sequential enantioselective organic transformations. This study presents the design of an integrated Cu/bisoxazoline and Ru/diamine co-catalyst system for the direct preparation of 1,3-distereocentered beta-sulfonamido alcohols. The cascade reaction enables efficient and selective synthesis of chiral products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Lotte Stockhammer, Maximilian Radetzky, Syeda Sadia Khatoon, Matthias Bechmann, Mario Waser
Summary: A two-step protocol for the asymmetric synthesis of novel chiral benzofused ε-lactones starting from O-protected hydroxymethyl-para-quinone methides and activated aryl esters is reported. The use of chiral isothiourea Lewis base catalysts allows the obtaining of a broad variety of differently substituted products with high levels of enantioselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Caterina Pont, Tiziana Ginex, Christian Grinan-Ferre, Matthias Scheiner, Alexia Mattellone, Noemi Martinez, Elsa M. Arce, Yolanda Soriano-Fernandez, Marina Naldi, Angela De Simone, Marta Barenys, Jesus Gomez-Catalan, Belen Perez, Raimon Sabate, Vincenza Andrisano, Maria Isabel Loza, Jose Brea, Manuela Bartolini, Maria Laura Bolognesi, Michael Decker, Merce Pallas, F. Javier Luque, Diego Munoz-Torrero
Summary: Through virtual screening, a lead compound with potential anti-AD activity has been identified, showing activity against BACE-1 and cholinesterases, while also playing a role in inhibiting Ab42 and tau aggregation, improving memory, and increasing synaptic protein levels.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Elnaz Aledavood, Beatrice Selmi, Carolina Estarellas, Matteo Masetti, F. Javier Luque
Summary: This review focuses on therapeutic treatments for influenza, specifically targeting key viral proteins including the M2 proton channel and neuraminidase. The article highlights the efforts in studying the M2 proton channel and discusses the challenges in developing efficient small molecule inhibitors and dealing with resistant strains.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Article
Multidisciplinary Sciences
Marta Sanz-Gomez, Elnaz Aledavood, Marina Beroiz-Salaverri, Laura Lagartera, Elena Vega-Martin, Marta Gil-Ortega, Jose Cumella, Concepcion Perez, Francisco Javier Luque, Carolina Estarellas, Maria S. Fernandez-Alfonso, Ana Castro
Summary: In this study, a novel AMPK modulator, IND6, was identified to activate AMPK in endothelial cells and restore vascular function through increased NO production and vasodilation. These findings suggest the therapeutic potential of IND6 in treating vascular complications associated with obesity.
SCIENTIFIC REPORTS
(2022)
Article
Chemistry, Organic
Miriam Picciche, Alexandre Pinto, Rosa Griera, Joan Bosch, Mercedes Amat
Summary: The enantioselective synthesis of (-)-cylindricine H from (R)-phenylglycinol-derived tricyclic lactam 1 is reported. Key steps include the stereoselective generation of the quaternary C-10 stereocenter, the stereoselective introduction of the C-4 acetoxy and C-2 butyl substituents taking advantage of the lactam carbonyl functionality, and the assembly of the pyrrolidine ring with the required functionalized one-carbon chain at C-13 by intramolecular opening of an epoxide.
Article
Chemistry, Organic
Marina Diaz-Ruiz, Aina Urbina, Nuria Llor, Joan Bosch, Mercedes Amat, Feliu Maseras
Summary: This study reports the synthesis of a marine macrolide and investigates the mechanism of a specific reaction step. The chemoselectivity is found to be controlled by thermodynamics, which is supported by theoretical calculations and experimental studies.
Article
Chemistry, Medicinal
Filippo Basagni, Marina Naldi, Tiziana Ginex, F. Javier Luque, Francesca Fagiani, Cristina Lanni, Matteo Iurlo, Massimo Marcaccio, Anna Minarini, Manuela Bartolini, Michela Rosini
Summary: This study investigates the role of the reciprocal position of two hydroxyl functions in inhibiting the aggregation of beta-amyloid peptide. The results show that para- and ortho-derivatives effectively reduce amyloid fibrillization, while the meta-analogue has no activity. Electrochemical analyses indicate that the antiaggregating potency correlates with the oxidation potential. Mass spectrometry studies and quantum mechanical calculations reveal different modes of action for active para- and ortho-derivatives.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Pharmacology & Pharmacy
Irene Alvarez-Berbel, Alba Espargaro, Antonio Viayna, Ana Belen Caballero, Maria Antonia Busquets, Patrick Gamez, Francisco Javier Luque, Raimon Sabate
Summary: One of the pathological features of Alzheimer's disease is the formation of amyloid-beta plaques. Inhibiting the enzyme acetylcholinesterase can slow down this process, and compounds like apigenin and quercetin also have inhibitory effects on plaque formation. These compounds can also affect the structure of amyloid fibers. Molecular modeling studies suggest that these effects may be due to the binding of apigenin and quercetin to acetylcholinesterase. Additionally, these compounds can reduce the production of reactive oxygen species, suggesting their potential use in targeting multiple biological features of Alzheimer's disease.
Article
Chemistry, Organic
Arnau Calbo, Rosa Griera, Joan Bosch, Mercedes Amat
Summary: Starting from racemic diastereomeric mixtures of dimethyl-2-oxocyclohexanepropionic acids (4-6), enantiopure cis-decahydroquinolines were synthesized via a dynamic kinetic asymmetric transformation and subsequent stereoselective removal of the chiral inductor. The procedure involved cyclocondensation of keto-acids 4-6 with (R)-phenylglycinol to form two major oxazoloquinolone lactams, followed by a two-step removal of the phenylglycinol moiety and reduction of the lactam carbonyl.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Medicinal
Javier Vazquez, Tiziana Ginex, Albert Herrero, Christophe Morisseau, Bruce D. Hammock, F. Javier Luque
Summary: This study examines the suitability of quantum mechanically derived hydrophobic descriptors in the discovery of novel sEH inhibitors. Three-dimensional quantitative structure-activity relationship (3D-QSAR) pharmacophores were generated using a list of 76 known sEH inhibitors and validated with external datasets. The use of hydrophobic-based descriptors led to the identification of six compounds as inhibitors of the human enzyme with IC50 < 20 nM, including two with IC50 values of 0.4 and 0.7 nM.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2023)
Article
Chemistry, Physical
William J. Zamora, Antonio Viayna, Silvana Pinheiro, Carles Curutchet, Laia Bisbal, Rebeca Ruiz, Clara Rafols, F. Javier Luque
Summary: In recent years, the use of partition systems other than n-octanol/water has gained attention in studying the lipophilicity of compounds. The difference between n-octanol/water and toluene/water partition coefficients has been found to be valuable in understanding intramolecular hydrogen bonds and chameleon-like properties that affect solubility and permeability. This study reports the experimental toluene/water partition coefficients for a series of drugs and investigates the performance of two computational strategies for predicting log P-tol/w.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Applied
Arnau Calbo, Rosa Griera, Joan Bosch, Mercedes Amat
Summary: In this study, the first enantioselective total synthesis of Myrioneuron alkaloid schoberine B and its enantiomer schoberine B was achieved.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Xiangyi Jiang, Jing Li, Antonio Viayna, F. Javier Luque, Molly Woodson, Lanlan Jing, Shenghua Gao, Fabao Zhao, Minghui Xie, Karoly Toth, John Tavis, Ann E. Tollefson, Xinyong Liu, Peng Zhan
Summary: Compounds D1N8 and D1N52 have shown excellent inhibitory activity against SARS-CoV-2 3CL(pro) with low cytotoxicity, providing a foundation for the research of novel anti-SARS-CoV-2 agents.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Carmine Marco Morgillo, Antonio Lupia, Alessandro Deplano, Luciano Pirone, Bianca Fiorillo, Emilia Pedone, F. Javier Luque, Valentina Onnis, Federica Moraca, Bruno Catalanotti
Summary: FAAH is a key enzyme in controlling cannabinoid signaling, and research on the mechanism of action of the non-competitive inhibitor TPA14 has provided a theoretical basis for the design of effective drugs for the treatment of neuropathic pain and chronic inflammation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
