Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qingsong Deng, Aimin Yu, Lei Zhang, Xiangtai Meng
Summary: A stereospecific three-component domino reaction was revealed under catalyst-free conditions, leading to the synthesis of a wide range of benzothiophene-fused polycycles and eight-membered N-heterocycles. The control over product formation was achieved by regulating the stereoconfiguration of cyclohexane-1,2-diamines. The detailed mechanism and origin of the chemoselectivity were explored using density functional calculations, revealing the influence of intramolecular attractions and steric effects on the observed chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ouldouz Ghashghaei, Marina Pedrola, Francesca Seghetti, Victor V. Martin, Ricardo Zavarce, Michal Babiak, Jiri Novacek, Frederick Hartung, Katharina M. Rolfes, Thomas Haarmann-Stemmann, Rodolfo Lavilla
Summary: The participation of reactants in polarity inversion allows the continuation of productive domino processes in multicomponent reactions, leading to the discovery of novel reaction pathways and various polyheterocyclic scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Jacob C. Hood, Maksim V. Anokhin, Douglas A. Klumpp
Summary: N-Heterocyclic alcohols have been proven to be excellent substrates for superacid-promoted Friedel-Crafts reactions. The ionization of N-heterocyclic alcohols produces reactive, dicationic intermediates, leading to good to excellent yields of arylation products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Engineering, Chemical
Luana M. Rosendo, Ana Teresa Brinca, Bruno Pires, Goncalo Catarro, Tiago Rosado, Raquel P. F. Guine, Andre R. T. S. Araujo, Ofelia Anjos, Eugenia Gallardo
Summary: Natural products are widely used in industry, food, and therapy. Characterizing them chemically is vital to explore their potential applications. Microextraction techniques, which use less organic solvents and sample amount compared to classical techniques, have gained popularity but are still less used in natural product analysis. This manuscript reviews popular solid-based miniaturized sample preparation techniques and discusses their advantages, disadvantages, and main applications in determining compounds in natural products.
Article
Chemistry, Organic
Peter Langer
Summary: The domino reactions of heterocyclic enamines with chromone derivatives lead to the synthesis of a variety of annulated heterocyclic ring systems, with the reaction pathway depending on the substituent at position 3 of the chromone. Functional groups at the carbonyl group of the chromone at position 3 allow for further synthetic transformations, including additional ring closures.
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Masanori Nagatomo, Masayuki Inoue
Summary: Natural products with a high ratio of sp(3)-hybridized atoms and oxygen-substituted stereogenic centers are privileged structures for the development of pharmaceuticals and chemical probes. Developing radical-based convergent strategies is advantageous for assembling highly oxygenated natural products efficiently. The versatile intermolecular radical reactions demonstrated in the total syntheses showcase new insights for retrosynthetic analyses and streamline synthetic routes to bioactive natural products.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Dominik Scherrer, David Vogel, Ute Drechsler, Antonis Olziersky, Christof Sparr, Marcel Mayor, Emanuel Loertscher
Summary: The study used Au nanohole arrays as SERS substrates to monitor solid-phase deprotection and click reactions. The results showed that the SERS substrate exhibited reliability in terms of signal reproducibility and chemical stability, and could be used to identify solid-phase intermediate and products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Ismail Alahyen, Laure Benhamou, Vincent Dalla, Catherine Taillier, Sebastien Comesse
Summary: Acrylamides are versatile building blocks that can be easily obtained from common starting materials. Over the past 20 years, they have been shown to be efficient partners in domino reactions, leading to a variety of complex aza-heterocycles. Metal-free and metal-triggered reactions allow good control of the reactivity of polyvalent acrylamides, resulting in diverse synthetic outcomes.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Organic
Polyssena Renzi, Jacopo Scarfiello, Alberto Lanfranco, Annamaria Deagostino
Summary: This review discusses domino and multicomponent reactions mediated by light, with a focus on photocatalyst- and additive-free processes. The most recent advances in the synthesis of complex nitrogen-, oxygen-, sulphur-, and selenium-heterocycles, as well as multicomponent cascades, are analyzed with an emphasis on both experimental and mechanistic studies.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Nanoscience & Nanotechnology
Vincent Hahn, N. Maximilian Bojanowski, Pascal Rietz, Florian Feist, Mariana Kozlowska, Wolfgang Wenzel, Eva Blasco, Stefan Braese, Christopher Barner-Kowollik, Martin Wegener
Summary: Most light-based 3D printing methods rely on optical or chemical nonlinearities for polymerization reactions. Two-photon absorption is commonly used in 3D micro-and nanoprinting, but this article reviews three emerging processes that allow for quadratic nonlinearity without relying on two-photon absorption, namely upconversion luminescence, two-step absorption, and triplet-triplet annihilation. These (1 + 1)-photon absorption processes enable the use of continuous-wave lasers at lower peak powers and cost compared to two-photon absorption. The article discusses recent progress, challenges, and future perspectives.
Article
Biochemistry & Molecular Biology
Vivek Kumar, Jennifer S. Lin, Natalia Molchanova, John A. Fortkort, Carolin Reckmann, Stefan Braese, Havard Jenssen, Annelise E. Barron, Archana Chugh
Summary: Visceral leishmaniasis (VL) is a neglected tropical disease and the use of cell-permeating peptides as potential drug candidates to treat VL is limited due to their limited biological stability. In this study, peptoids, which are peptide mimics with good biostability, were tested against Leishmania donovani. The addition of N-alkyl hydrophobic chains and bromination yielded compounds with good antileishmanial activity against both intracellular amastigotes and promastigotes, indicating the potential of these peptoids as drug candidates for VL.
Article
Chemistry, Multidisciplinary
Dimitry Schmidt, Patrizia Gartner, Ivan Berezkin, Jens Rudat, Maximilian Bilger, Tom Gruenert, Nadine Zimmerer, Philipp Quarz, Philip Scharfer, Julian Brueckel, Andre P. Jung, Pooja Singh, Pooja Pooja, Benno Meier, Mareen Stahlberger, Wilhelm Schabel, Stefan Braese, Gisela Lanza, Alexander Nesterov-Mueller
Summary: This study presents a method to screen for selective peptide binders to perfluorinated sulfonic acid ionomers, such as Nafion, using ultra-high density peptide arrays. The peptide WIWHCW with a helix structure is identified as a selective binder to Nafion, and the invariant amino acids responsible for binding are also determined. The dissociation constant of WIWHCW to Nafion is measured at approximately 140 μM.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Review
Chemistry, Multidisciplinary
Valentina Ferraro, Clara R. Adam, Aleksandra Vranic, Stefan Braese
Summary: The use of visible light for polymerization is appealing for its potential in improving the sustainability of the process. Transition metal complexes, with their long-lived excited states and reversible redox properties, are a viable option for photoinitiating systems. This review provides an overview of the transition metal complexes used in photopolymerization reactions, with particular emphasis on recent applications in 3D printing and the challenges in achieving highly efficient and sustainable processes.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Materials Science, Multidisciplinary
Ilona Wagner, Simon Spiegel, Julian Brueckel, Matthias Schwotzer, Alexander Welle, Martina H. H. Stenzel, Stefan Braese, Salma Begum, Manuel Tsotsalas
Summary: Surface engineering of MOF NPs using dynamic modification strategies enables the tailoring of PEG-grafted MOF NPs with improved colloidal stability and high dispersity, while maintaining their morphology and lattice crystallinity. The PEG-grafted MOF NPs show reduced adsorption of HSA protein compared to uncoated ones, indicating the potential for reducing nonspecific interactions and introducing targeting moieties for specific interactions. This approach expands the applications of colloidal MOF NPs in biologically relevant fields.
MACROMOLECULAR MATERIALS AND ENGINEERING
(2023)
Article
Biochemistry & Molecular Biology
Alaa A. Hassan, Ashraf A. Aly, Mohamed Ramadan, Nasr K. Mohamed, Bahaa G. M. Youssif, Hesham A. M. Gomaa, Stefan Braese, Martin Nieger, Amal S. Abd El-Aal
Summary: The diastereoselective reaction between N,N''-1,omega-alkanediylbis[N '-organylthiourea] derivatives and 2,3-diphenylcyclopropenone in refluxing ethanol resulted in the formation of two enantiomers of 3-substituted-1-[2-(5)-3-substituted-4-benzyl-5-oxo-4-phenyl-2-thioxoimid-azolidin-1-yl]ethyl/propyl-5-benzyl-5-phenyl-2-thioxoimidazolidin-4-ones. The isolated compounds were characterized using various techniques, including NMR, IR, mass spectra and elemental analyses, and their structures were elucidated using X-ray crystallography. The tested compounds exhibited significant antiproliferative activity as well as EGFR inhibitory effects, with compound 4c (R = allyl, n = 3) showing the most potent antiproliferative effect and the highest inhibitory effect on EGFR.
MOLECULAR DIVERSITY
(2023)
Review
Biochemistry & Molecular Biology
Ashraf A. Aly, Elham M. Abdallah, Salwa A. Ahmed, Mai M. Rabee, Stefan Braese
Summary: This review highlights interesting and recent applications of transition metals in the complexation of thiosemicarbazides, thiocarbohydrazides, and their corresponding carbazones. The review discusses the chosen five metals, their electronic configurations, and the stability of the complexes. It also presents different synthesis routes and examples of Cu(I), Cu(II), Co(II), Ni(II), Ag(I), and Pd(II) complexes of thiosemicarbazide and thiocarbohydrazide. Furthermore, the review summarizes the catalytic use of metal complexes of thiosemicarbazones and thiocarbazones ligands, as well as their biological importance.
Article
Materials Science, Multidisciplinary
Zhen Zhang, Peng Wu, Ke Wang, Hong Lin, Eduard Spuling, Rongrong Xia, Youjun Wu, Jin Cao, Jianhua Zhang, Bin Wei, Stefan Braese, Zixing Wang
Summary: This study reports the development of white organic light-emitting diodes (WOLEDs) based on platinum complexes with tunable correlated color temperature (CCT). By methylating the ligand, the interaction between Pt(II) complexes was regulated, resulting in adjustable emission and CCT of the WOLEDs. High device performances with high external quantum efficiency and low efficiency roll-offs were achieved using exciplex as a host. Moreover, the CCT of the WOLEDs could be tuned by changing the driving voltages, matching with the daylight spectrum.
ACS MATERIALS LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Christin Bednarek, Ute Schepers, Franziska Thomas, Stefan Braese
Summary: With the development of bioconjugation chemistry in the past two decades, particularly highlighted by the Nobel Prize in 2022, the search for new applications has intensified, expanding the possibilities of these simple, specific, and high-yield reactions. The advancement of bioconjugation methods is expected to enhance the field of bioinstructive and bioadaptive materials science in the future. This article discusses the recent developments in coupling various biological entities, such as polysaccharides, oligonucleotides, peptides, and proteins, and explores the impact of bioconjugation reactions in materials science and 3D printing, along with their challenges and requirements.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Frank Tristram, Nicole Jung, Patrick Hodapp, Rasmus R. Schroeder, Christof Woell, Stefan Braese
Summary: This article describes the latest methods of research data management (RDM) in academia, as well as the future prospects of digitalized molecular material workflows. The different elements of an integrated research data management strategy are described, and examples of automated processes are depicted. The use of electronic lab notebooks, data-integration and data-conversion strategies, and the establishment of two platforms for automated synthesis and analysis of materials are highlighted. Two examples of beneficial effects of successful RDM strategies are presented, including a sophisticated tool for data prediction based on machine learning and options for creating community-driven databases.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Review
Chemistry, Multidisciplinary
Steven C. Gauci, Aleksandra Vranic, Eva Blasco, Stefan Braese, Martin Wegener, Christopher Barner-Kowollik
Summary: This article evaluates recent advances in photoresist design for light-driven 3D printing and provides an outlook on the challenges and opportunities. By classifying the photoresists into chemistries that function photoinitiator-free and those that require a photoinitiator, their capabilities and limitations are comprehensively understood.
ADVANCED MATERIALS
(2023)
Article
Biochemistry & Molecular Biology
Lamya H. Al-Wahaibi, Hesham A. Abou-Zied, Mohamed Hisham, Eman A. M. Beshr, Bahaa G. M. Youssif, Stefan Brase, Alaa M. Hayallah, Mohamed Abdel-Aziz
Summary: A series of novel 3-cyanopyridone/pyrazoline hybrids exhibiting dual inhibition against EGFR and BRAF(V600E) have been developed and demonstrated remarkable antiproliferative activity and promising anticancer potential.
Article
Biochemistry & Molecular Biology
Mohamed T-E Maghraby, Tahani Mazyad Almutairi, Stefan Brase, Ola I. A. Salem, Bahaa G. M. Youssif, Mahmoud M. Sheha
Summary: A novel series of 1,2,3-triazole/1,2,4-triazole hybrids were designed and synthesized as antiproliferative agents targeting aromatase enzymes. Compounds 6a and 6b demonstrated the highest antiproliferative activity and aromatase inhibitory action, indicating their potential as anticancer candidates. Molecular docking investigations further supported these findings.
Article
Chemistry, Medicinal
Lamya H. Al-Wahaibi, Essmat M. El-Sheref, Alaa A. Hassan, S. Braese, M. Nieger, Bahaa G. M. Youssif, Mahmoud A. A. Ibrahim, Hendawy N. Tawfeek
Summary: 2,3,4-trisubstituted thiazoles 3a-i were successfully synthesized and their structures were determined. These compounds showed excellent antiproliferative activity without exhibiting cytotoxicity. The most potent derivatives, compounds 3a, 3c, 3d, and 3f, demonstrated strong antiproliferative activity against human cancer cell lines and also exhibited potent inhibition against EGFR and BRAF(V600E).
Article
Chemistry, Medicinal
Lamya H. Al-Wahaibi, Mohamed Hisham, Hesham A. Abou-Zied, Heba A. Hassan, Bahaa G. M. Youssif, Stefan Braese, Alaa M. Hayallah, Mohamed Abdel-Aziz
Summary: A novel series of hybrid compounds with dual inhibitory actions on EGFR and BRAF(V600E) were developed. These compounds exhibited significant inhibition of cell proliferation and minimal toxicity.
