Article
Chemistry, Multidisciplinary
Valeriia Hutskalova, Alessandro Prescimone, Christof Sparr
Summary: The study of new synthetic routes for positively charged N-heterocycles is crucial for the advancement of medicinal chemistry, functional materials, catalysis, and other applications. By utilizing phenanthryne as the aryne component, a novel synthetic methodology was developed to form a helical tetrabenzophenanthridinium derivative, which exhibited susceptibility to photoinduced cyclodehydrogenation. The photophysical and electrochemical properties of the resulting compound were also determined.
HELVETICA CHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Nicolaj Inunnguaq Jessen, Maksimilian Bura, Giulio Bertuzzi, Karl Anker Jorgensen
Summary: An efficient and stereoselective synthesis of chiral cycl[3.2.2]azines has been achieved through the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion catalysis. The method allows for incorporation of diverse enals and the obtained products can undergo selective transformations while retaining stereochemical information established in the [8+2] cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Applied
Ahmad Saifuddin Mohamad Arshad, Mohd Nizam Mordi
Summary: Carbolines are a prominent class of tricyclic alkaloids found in natural products, and there are four different regioisomers known. Synthetic methods have been established for the construction of carboline frameworks, both requiring customized approaches for each regioisomer and unified approaches capable of generating multiple regioisomers. This review summarizes the construction of isomeric carbolines based on unified synthetic approaches.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Vladimir V. Voronin, Maria S. Ledovskaya, Konstantin S. Rodygin, Valentine P. Ananikov
Summary: This work presents a universal synthetic approach for the synthesis of D-2-labeled nitrogen heterocycles through cycloaddition reactions using in situ generated dideuteroacetylene. By using 1,4-dioxane as a solvent, the method allowed for high levels of deuteration up to 99%. It was demonstrated to be suitable for the synthesis of various D-2-labeled heterocycles such as triazoles, isoxazoles, pyrazoles, and pyridazines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Yuting Tian, Ziyang Chen, Kexin Su, Yongsheng Zheng, Jikai Liu
Summary: In this study, an acetic acid-catalyzed [2+2+1+1] cycloaddition reaction between 1,3,5-triazinanes and methylene compounds was developed. The reaction provides a straightforward approach to hexahydropyrimidines in mild conditions with good yields and potential applications. This work represents a novel reaction system.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yang Feng, Bo Chang, Yuanyuan Ren, Fangxia Zhao, Ke-Hu Wang, Junjiao Wang, Danfeng Huang, Xiaobo Lv, Yulai Hu
Summary: An efficient and practical method for the synthesis of trifluoromethylpyrrolopyrazole derivatives was developed by utilizing readily available trifluoromethyl building blocks in a [3+2] cycloaddition reaction. The reaction proceeds smoothly under mild conditions, providing good to excellent yields of 3-trifluoromethylated pyrrolidino[3,4-c]pyrazolidin-4,6-dione and 3-trifluoromethylated dihydropyrrolo[3,4-c]pyrazole-4,6(1H,5H)-diones. The latter can be further oxidized to 3-trifluoromethylated pyrrolo[3,4-c]pyrazole-4,6(1H,5H)-diones using TCCA.
Review
Chemistry, Applied
Dimitris Matiadis
Summary: 2-Pyrazolines are important five-membered heterocycles with two adjacent nitrogen atoms. They have various functional groups and unique biological properties, and are used as building blocks. In recent years, there has been significant progress in the synthesis of 2-pyrazolines, with the development of novel strategies and improvements of existing protocols. This review summarizes the synthetic methodologies from 2012 to 2022, discussing the challenges, capabilities, scopes, and limitations of the reactions, as well as substitution patterns and mechanisms where applicable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Rui Chang, Yubing Pang, Juntao Ye
Summary: This study reports a photoinduced approach for hydroarylation of unactivated olefins using 4-hydroxycoumarins as the arylating reagent. The key to the success of this reaction is the conversion of nucleophilic 4-hydroxycoumarins into electrophilic carbon radicals through photocatalytic arene oxidation. This method not only overcomes the polarity-mismatch issue encountered under ionic conditions but also allows for a broad substrate scope and inhibits side reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa
Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yong-Ji Hu, Yu Zhou, Jing-Jing Gao, Han Zhang, Kai-Rui Yang, Jia-Jun Li, Xiao-Xin Yan, Yuan-Lin Li, Yan-Ping Zhu
Summary: In this study, an I-2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides was demonstrated. This method allows for the selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles, with the potential for further chemical modifications of the iodine-functionalized products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Biochemistry & Molecular Biology
Biswajit Panda, Gianluigi Albano
Summary: Nicotine, a chiral alkaloid found in tobacco plants, targets and stimulates nicotinic acetylcholine receptors, leading to interest in developing synthetic analogues. Current research focuses on synthesizing conformationally restricted analogues of nicotine using various catalytic processes. Biological studies on the activity of these analogues on specific nAChR subunits are also considered.
Article
Chemistry, Organic
Merlin Kleoff, Lisa Boeser, Linda Baranyi, Philipp Heretsch
Summary: A metal-free synthesis method for benzotriazoles in flow using azides and in situ generated arynes is reported. The modular access to benzotriazoles is provided by employing different substitution patterns of the azide and aryne coupling partners. The safety profile of the process is improved by minimizing thermal strain of hazardous azides and accumulation of reactive intermediates through short reaction times in flow. The scalability of the reaction is also demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Jordan L. Harper, Stephanie Felten, Ryan M. Stolley, Alexander S. Hegg, Paul H-Y Cheong, Janis Louie
Summary: The mechanistic investigation into the origins of regio- and chemoselectivities observed in iron/pyridine dialdimine (PDAI)-catalyzed intermolecular [2+2+2] cycloaddition reactions of terminal alkynes and cyanamides reveals the significant role of the hemilabile PDAI ligand in controlling the observed selectivity of the resultant products.
Article
Chemistry, Multidisciplinary
Ming Zhang, Xiao-Chen Wang
Summary: This method presents a mild and efficient approach for synthesizing enantioenriched tetrahydroquinoline-fused cyclobutenes through a cascade reaction, catalyzed by chiral spiro-bicyclic bisboranes. The bisboranes function by catalyzing hydride transfer and activating the alkynone substrate for an enantioselective cycloaddition reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
Genetics & Heredity
Mame Yoro Diallo, Martina Cizkova, Iva Kulichova, Eliska Podgorna, Edita Priehodova, Jana Novackova, Veronica Fernandes, Luisa Pereira, Viktor Cerny
Summary: The Sahara Desert has had a significant influence on African history, acting as a barrier for migrations. However, there have been instances of gene flow between North Africa and sub-Saharan populations. This study analyzed mitochondrial DNA diversity to demonstrate the importance of maternal gene flow in the circum-Saharan region, showing connections between North Africa and the Sahel/Savannah belt.
Article
Biochemical Research Methods
Veronika Solinova, Petr Tuma, Maria Butnariu, Vaclav Kasicka, Dusan Koval
Summary: We present a method for finely adjustable electroosmotic flow (EOF) velocity in cathodic direction for the optimization of separations in capillary electrophoresis. The method involves surface modification of the separation fused silica capillary using a covalently attached copolymer to control the charge density and achieve adjustable EOF. The properties of EOF in the treated capillaries are observed and the importance of adjustable EOF in separations is demonstrated.
Article
Biochemistry & Molecular Biology
Cesar Fortes-Lima, Petr Triska, Martina Cizkova, Eliska Podgorna, Mame Yoro Diallo, Carina M. Schlebusch, Viktor Cerny
Summary: The study reveals fine-scale population structure and complex admixture patterns among populations in the Sahel/Savannah belt, with the Rashaayda Arabic-speaking population showing lack of gene flow from African groups, and Western Sahelian populations exhibiting signatures of selection in various genetic regions.
MOLECULAR BIOLOGY AND EVOLUTION
(2022)
Article
Chemistry, Analytical
Petr Tuma, Blanka Sommerova, Dusan Koval, Michaela Siklova, Michal Koc
Summary: This study presents a sensitive electrophoretic method for determining 3-hydroxybutyrate (3HB) levels, which is an indicator of human ketogenesis. By using a specially coated capillary and optimizing the separation conditions, baseline separation of 3HB from other components in human serum can be achieved. The method shows low limits of detection and quantification, making it suitable for monitoring physiological 3HB levels.
Article
Chemistry, Inorganic & Nuclear
Jiri Schulz, Jakub Antala, Ivana Cisarova, Petr Stepnicka
Summary: Compared to phosphine counterparts, little attention has been paid to the study of ferrocene stibines. This paper describes the synthesis of ferrocene stibine derivatives and their reactivity and coordination behavior. The compounds were characterized through various spectroscopic techniques and crystallography. The research findings reveal important insights into the structural parameters and electrochemical properties of the ferrocene stibines, but their catalytic efficiency needs to be further improved in Suzuki-Miyaura biaryl coupling reactions.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Zuzana Kotkova, Filip Koucky, Jan Kotek, Ivana Cisarova, David Parker, Petr Hermann
Summary: A series of Cu(II) complexes with cyclam-based ligands containing two N-(2,2,2-trifluoroethyl)-aminoalkyl pendant arms were studied for their potential use as F-19 MRI contrast agents. Structural analysis and NMR measurements revealed the formation of isomeric complex species in solution. The Cu(II) ion showed significant relaxation enhancement and can be considered as a highly suitable metal ion for efficient F-19 MRI contrast agents.
DALTON TRANSACTIONS
(2023)
Article
Evolutionary Biology
Mederic Mouterde, Youssef Daali, Victoria Rollason, Martina Cizkova, Anwar Mulugeta, Khalid A. Al Balushi, Giannoulis Fakis, Theodoros C. Constantinidis, Khalid Al-Thihli, Marie Cerna, Eyasu Makonnen, Sotiria Boukouvala, Said Al-Yahyaee, Getnet Yimer, Viktor Cerny, Jules Desmeules, Estella S. Poloni
Summary: Variations in genes involved in drug ADME can affect individual response to treatment. This study assessed phenotypic variation in four populations across Africa, the Middle East, and Europe and found significant population differentiation for most drug metabolism phenotypes. Genome-wide association studies identified genetic variants associated with phenotypic variation in certain drug metabolism enzymes. However, no association was found for other enzymes, suggesting different evolutionary mechanisms shaping these phenotypes.
GENOME BIOLOGY AND EVOLUTION
(2022)
Article
Chemistry, Organic
Adela Krizkova, Guillaume Bastien, Igor Roncevic, Ivana Cisarova, Jiri Rybacek, Vaclav Kasicka, Jiri Kaleta
Summary: In this study, a radical chlorination reaction of cubane-1,4-dicarboxylic acid was reported, resulting in the preferential formation of a monochlorinated derivative (approximately 70%) along with four dichlorinated derivatives (approximately 20% in total). The positions of the chlorine atoms were confirmed by X-ray diffraction analysis. The acidity constants of the different chlorinated cubane dicarboxylates were determined, and their thermal stability was evaluated using differential scanning calorimetry. The reaction pathways and strain energies of the derivatives were investigated through computational calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Andrea Vopalenska, Vojtech Docekal, Simona Petrzelova, Ivana Cisarova, Jan Vesely
Summary: The present study reports an asymmetric organocascade reaction that efficiently catalyzes the reaction between oxindole-derived alkenes and 3-bromo-1-nitropropane using a bifunctional catalyst. The reaction produces spirooxindole-fused cyclopentanes in moderate-to-good isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol is demonstrated through additional transformations of the resulting spirooxindole compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ladislav Loska, Vojtech Docekal, Ivana Cisarova, Jan Vesely
Summary: The study presents an asymmetric NHC-catalyzed formal [4 + 2] cycloaddition of heterocyclic alkenes with an azolium-dienolate intermediate. The reaction is achieved without external oxidation of the Breslow intermediate. Good yields (typically about 90%) and stereochemical outcomes (in most cases, dr > 20/1, and ee = 70-99%) were obtained for heterocyclic cyclohexenones. The synthetic utility of the protocol was demonstrated by the scope of heterocyclic alkenes.
Article
Chemistry, Analytical
Petr Tuma, Blanka Sommerova, Dusan Koval, Michaela Siklova, Michal Koc
Summary: In this study, capillary electrophoresis was used to determine minor nitrogen metabolites, including creatine, 2-aminobutyric acid (2-AB), and acetyl-carnitine (Ac-carn), in human plasma. Baseline separation of these metabolites was achieved using a 6% PAMAPTAC coated fused silica capillary and a counter-current mode. Plasma levels of these metabolites were monitored during a 60-hour fasting period, and significant differences were observed compared to baseline levels.
MICROCHEMICAL JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Michal Navratil, Ivana Cisarova, Petr Stepnicka
Summary: This study describes the synthesis of two functional phosphines and their coordination behavior with palladium. The results show that the two compounds form different complexes with palladium.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Viraj A. Bhosale, Ivana Cisarova, Martin Kamlar, Jan Vesely
Summary: This study presents a novel chiral phosphoric acid (CPA)-catalyzed reaction, allowing for the asymmetric addition of alpha-fluoro(phenylsulfonyl)methane (FSM) derivatives to in situ generated cyclic N-acyliminium. The process demonstrates high stereoselectivity, leading to the formation of biorelevant isoindolinones containing sulfone and fluorine substituents with excellent stereoselectivities.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Jan Choutka, Michal Kratochvil, Ivana Cisarova, Radek Pohl, Jakub Kaminsky, Kamil Parkan
Summary: This manuscript presents an early investigation on the synthesis, structure, and conformational behavior of a novel type of glycomimetics called (1 -> 1)-Si-disaccharides. The study shows that these glycomimetics have good stability and flexibility in conformation, which differs from natural carbohydrates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Jiri Schulz, Ivana Cisarova, Robert Gyepes, Petr Stepnicka
Summary: The reactions of a gold(I) metalloligand with bare or ligand-stabilised group 11 metal ions lead to the formation of diverse oligometallic clusters stabilized by different types of interactions. The unique properties of the bridging ferrocene groups enable the accommodation of capping moieties and supporting ligands, resulting in the formation of structurally unique products. The strength of the metallophilic interaction between gold and the other metal ions determines the behavior of the capping reactions.
DALTON TRANSACTIONS
(2022)
