Review
Chemistry, Multidisciplinary
Disha P. Vala, Ruturajsinh M. Vala, Hitendra M. Patel
Summary: This review summarizes the synthetic routes used in the past 21 years for the synthesis of 1,2,3-triazoles and their derivatives. It includes the use of various metal catalysts, organocatalysts, and metal-free approaches. The constant developments in this field indicate the importance of 1,2,3-triazoles in future organic synthesis and molecular library creation.
Article
Biochemistry & Molecular Biology
Aida Buza, Cuneyt Turkes, Mustafa Arslan, Yeliz Demir, Busra Dincer, Arleta Rifati Nixha, Sukru Beydemir
Summary: Sulfonamides bearing 1,2,3-triazole moiety were designed as inhibitors of human alpha-carbonic anhydrases (hCAs). Some derivatives showed selectivity towards the hCA I and II isoforms. The synthesized compounds demonstrated significant antiproliferative activity and minimal cytotoxicity in various cell lines.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Inorganic & Nuclear
Alessandro Di Girolamo, Filippo Monti, Andrea Mazzanti, Elia Matteucci, Nicola Armaroli, Letizia Sambri, Andrea Baschieri
Summary: This study successfully synthesized five cationic iridium(III) complexes using phenyl-triazole derivatives, including the less explored tris-heteroleptic analogues. The redox and emission properties of the complexes can be effectively tuned by different ligands. The complexes equipped with bipyridine ancillary ligand exhibit reversible redox processes and high emission quantum yields, while the complexes equipped with high-field isocyanide ligands display irreversible redox processes and high-energy emission with low quantum yields.
INORGANIC CHEMISTRY
(2022)
Review
Chemistry, Analytical
Ivan Torres-Moya, Jose Ramon Carrillo, Angel Diaz-Ortiz, Pilar Prieto
Summary: BTz is an excellent candidate in material science, with self-assembly ability, acceptor character, and ease of modulation. It can be used to produce various derivatives for applications in different fields such as optoelectronics or biomedicine.
Article
Environmental Sciences
Emad K. Radwan, Huda R. M. Rashdan, Bahaa A. Hemdan, Asmaa A. Koryam, Mehrez E. El-Naggar
Summary: This study reports the synthesis of a novel sulfone biscompound for the removal of dyes and disinfection of water contaminated with pathogens. The sulfone biscompound efficiently removes cationic dyes and exhibits powerful antibacterial potential, effectively eliminating tested pathogens.
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2022)
Article
Chemistry, Inorganic & Nuclear
Iryna S. Kuzevanova, Olesia I. Kucheriv, Volodymyr M. Hiiuk, Dina D. Naumova, Sergiu Shova, Sergii I. Shylin, Volodymyr O. Kotsyubynsky, Aurelian Rotaru, Igor O. Fritsky, Il'ya A. Gural'skiy
Summary: This study reports the first Fe-II Hofmann clathrate analogues with unsubstituted 1,2,3-triazole, which exhibit temperature induced spin transition. The two new coordination polymers undergo abrupt hysteretic spin crossover in the range of 190-225 K, displaying a stable thermal hysteresis loop and strong thermochromic effect. The use of 1,2,3-triazole in spin-crossover Hofmann clathrate analogues can advantageously expand the family of complexes.
DALTON TRANSACTIONS
(2021)
Article
Biochemistry & Molecular Biology
Huda R. M. Rashdan, Ihsan A. Shehadi, Mohamad T. Abdelrahman, Bahaa A. Hemdan
Summary: The synthesized compound exhibited strong antibacterial effects against all tested strains, with Gram-negative species being more susceptible. Toxicity tests showed the compound to be biocompatible and safe. Molecular docking studies indicated interactions with key enzymes, stabilizing the compound and demonstrating its antimicrobial activity.
Article
Chemistry, Multidisciplinary
Qi-Yuan Yang, Rui Ma, Yun-Qiong Gu, Xiao-Fang Xu, Zhen-Feng Chen, Hong Liang
Summary: Targeting metabolic reprogramming to treat cancer, by using arene-ruthenium(II)/osmium(II) complexes to potentiate the anticancer effect of metformin (Met.) via glucose metabolism reprogramming, could increase overall survival and reduce side effects.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Alexander N. Koronatov, Kseniia K. Afanaseva, Pavel A. Sakharov, Nikolai V. Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A new method for the synthesis of 1-alkyl-3-sulfonamido-1H-pyrroles via the Rh(ii)-catalyzed denitrogenative coupling of two different types of 1,2,3-triazoles has been developed. The reaction mechanism involves the attack of the rhodium-bound azavinyl carbene, leading to the formation of metal-free ylides and subsequent conversion to the desired products. This protocol provides high yields of 3-sulfonamidopyrroles, demonstrating promising synthetic applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Engineering, Environmental
Shangbiao Feng, Yunlu Li, Qi Lai, Jinxiong Cai, Zhe Wang, Ping Yin, Chunlin He, Siping Pang
Summary: A series of multi-functionalized 4-nitro-1,2,3-triazole based C-N linked biheterocyclic energetic compounds were synthesized, with representative compounds showing great potential as melt-castable explosive and high-performance insensitive energetic material. Additionally, a functionalized N8-branched compound with improved impact sensitivity and friction sensitivity was successfully prepared.
CHEMICAL ENGINEERING JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Saona Seth, Chayanika Pathak
Summary: Energetic materials containing azoles are appealing due to their high nitrogen content and functional groups that can participate in non-covalent bonding interactions. The compound 4,4'-azobis(1,2,4-triazole) (ATRZ) has been used as a molecular precursor to derive tailor-made energetic materials with hydrogen-bond acceptor and metal coordination sites. This review discusses the development of energetic cocrystals, coordination polymers, and composites using ATRZ as a high-energy molecular scaffold.
CRYSTAL GROWTH & DESIGN
(2023)
Review
Chemistry, Inorganic & Nuclear
Pascale Crochet, Victorio Cadierno
Summary: This review article focuses on the catalytic applications of arene-osmium(II) complexes, discussing transfer hydrogenation, hydrogenation, oxidation, and nitrile hydration reactions, as well as different C-C bond forming processes comprehensively, showing that they can achieve comparable or superior effectiveness in some instances compared to their ruthenium analogues.
Review
Chemistry, Medicinal
Harish C. Upadhyay
Summary: The widespread use of antibiotics has led to bacterial resistance and recurrent infections. To overcome this issue, multidrug therapy or single drugs acting on multiple targets may be utilized. Natural product-based hybrid molecules may provide a super alternative to combat drug resistance caused by various bacterial and fungal strains.
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Jonas F. Schlagintweit, Christian H. G. Jakob, Kevin Meighen-Berger, Thomas F. Gronauer, Angela Weigert Munoz, Vanessa Weiss, Matthias J. Feige, Stephan A. Sieber, Joao D. G. Correia, Fritz E. Kuehn
Summary: Fluorescent Pd(II) and Pt(II) complexes with 4-methylene-7-methoxycoumarin (MMC) and 2,6-diisopropylphenyl (Dipp) substituted NHC/1,2,3-triazole hybrid ligands were described, showing antiproliferative activity against cervix and breast cancer cells, with the tetradentate coordination mode being notably more effective. The Pd(s) complex with bidentate coordination mode was only active against HeLa, exhibiting high selectivity for cancer cells compared to healthy skin cells. The compound is believed to be located in late endosomes or lysosomes according to fluorescence microscopy.
DALTON TRANSACTIONS
(2021)
Article
Multidisciplinary Sciences
Mohammed A. Baashen
Summary: The current work reports the synthesis of novel hydrazones and bis-hydrazones containing 1,2,3-triazole moiety. The target compounds were successfully synthesized using different reaction conditions and catalysts, and were fully characterized. The synthesized heterocycles showed moderate antibacterial activity against Staphylococcus aureus and Listeria monocytogenes.
JOURNAL OF TAIBAH UNIVERSITY FOR SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Valentin Fuchs, Klaudia Cseh, Michaela Hejl, Petra Vician, Benjamin Neuditschko, Samuel M. Meier-Menches, Lukas Janker, Andrea Bileck, Natalie Gajic, Julia Kronberger, Martin Schaier, Sophie Neumayer, Gunda Koellensperger, Christopher Gerner, Walter Berger, Michael A. Jakupec, Michael S. Malarek, Bernhard K. Keppler
Summary: A series of highly lipophilic Cp-substituted molybdenocenes with different bioactive chelating ligands were synthesized and characterized. They showed significantly increased cytotoxic potency compared to non-Cp-substituted counterparts. In vivo experiments demonstrated tumor growth inhibition for the most active complex containing the thioflavone ligand, along with significant regulation of tubulin-associated and mitochondrial inner membrane proteins.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Pharmacology & Pharmacy
Janos P. Meszaros, Wolfgang Kandioller, Gabriella Spengler, Alexander Prado-Roller, Bernhard K. Keppler, Eva A. Enyedy
Summary: This study introduces half-sandwich Rh complexes that can be activated in the acidic, extracellular pH of tumor tissue, reducing the side effects and improving the efficacy of chemotherapy.
Article
Chemistry, Inorganic & Nuclear
Christopher Wittmann, Tim Gruene, Alexander Prado-Roller, Sandra Arandelovic, Johannes Reynisson, Vladimir B. B. Arion
Summary: A series of latonduine derivatives were synthesized and characterized using spectroscopic and mass spectrometry techniques. The molecular structures of some compounds were confirmed by X-ray diffraction or electron diffraction. The antiproliferative activity of these compounds in different cancer cells and normal cells was evaluated by MTT assays.
Article
Chemistry, Multidisciplinary
Philipp Spiess, Ana Sirvent, Irmgard Tiefenbrunner, Jules Sargueil, Anthony J. Fernandes, Ana Arroyo-Bondia, Ricardo Meyrelles, David Just, Alexander Prado-Roller, Saad Shaaban, Daniel Kaiser, Nuno Maulide
Summary: p-Toluenesulfonyl (Tosyl) and nitrobenzenesulfonyl (Nosyl) are widely used sulfonyl protecting groups for amines in organic synthesis. However, p-toluenesulfonamides are difficult to remove in multistep synthesis, while nitrobenzenesulfonamides are not stable under various reaction conditions. In this study, we introduce a new sulfonamide protecting group called Nms, which overcomes these limitations and shows superiority in terms of stability and cleavability.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Correction
Pharmacology & Pharmacy
M. S. Galanski, V. B. Arion, M. A. Jakupec, B. K. Keppler
CURRENT PHARMACEUTICAL DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Alexander Kastner, Hemma Schueffl, Patrick A. Yassemipour, Bernhard K. Keppler, Petra Heffeter, Christian R. Kowol
Summary: Platinum(IV) prodrugs are promising alternatives to platinum(II) anticancer therapeutics. This study investigated the reactivity and synthetic usability of a platinum(IV) complex with hydrolyzable equatorial ligands, and successfully synthesized stable platinum(IV) complexes suitable for long-circulating tumor-targeting strategies. Additionally, platinum(IV) complexes with equatorial maleimides were synthesized, showing prolonged plasma half-life and improved anticancer activity compared to oxaliplatin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Correction
Oncology
Mathea Sophia Galanski, Bernhard K. K. Keppler
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
(2023)
Article
Oncology
Monika Caban, Bettina Koblmueller, Diana Groza, Hemma H. Schueffl, Alessio Terenzi, Alexander Tolios, Thomas Mohr, Marlene Mathuber, Kushtrim Kryeziu, Carola Jaunecker, Christine Pirker, Bernhard K. Keppler, Walter Berger, Christian R. Kowol, Petra Heffeter
Summary: Through chemical modifications, KP2187 has similar activity and action as other clinically used EGFR inhibitors, without interfering with EGFR binding. In vitro and in vivo experiments have shown that KP2187 can significantly inhibit tumor cell proliferation and activate the EGFR signaling pathway. Moreover, KP2187 has a high synergistic effect with VEGFR inhibitors, indicating its potential as a hypoxia-activated prodrug.
Article
Chemistry, Applied
Alexia Tialiou, Zahraa H. Athab, Robert T. Woodward, Veronika Biegler, Bernhard K. Keppler, Ahmed F. Halbus, Michael R. Reithofer, Jia Min Chin
Summary: A novel hydroxypropyl cellulose (gHPC) hydrogel with graded porosity was successfully synthesized by cross-linking different parts of the hydrogel at different temperatures. The pore size in the hydrogel decreased from top to bottom. The hydrogel also showed graded mechanical properties, with the top layer being able to withstand 50% compression before fracture, while the middle and bottom layers could withstand 80% compression.
CARBOHYDRATE POLYMERS
(2023)
Article
Materials Science, Paper & Wood
Yuko Yoneda, Toshinari Kawada, Markus Bacher, Alexander Prado-Roller, Hubert Hettegger, Antje Potthast, Alfred D. French, Thomas Rosenau
Summary: Cellulose model compounds are widely used in cellulose research to study the polymer's properties. By synthesizing methyl 4-O-methyl beta-D-glucopyranoside derivatives with different substitution patterns, the solid-state structures of these compounds were determined using X-ray diffraction. Solid-state C-13 NMR measurements confirmed the influence of packing arrangement on the chemical shifts of the substituted carbons.
Correction
Biochemistry & Molecular Biology
Mathea Sophia Galanski, Michael A. Jakupec, Bernhard K. Keppler
CURRENT MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Xiao Liu, Dominik Wenisch, Philipp Dahlke, Paul M. Jordan, Michael A. Jakupec, Christian R. Kowol, Phil Liebing, Oliver Werz, Bernhard K. Keppler, Wolfgang Weigand
Summary: In recent decades, the close connection between inflammation and cancer has been recognized, leading to extensive studies on joint strategies involving chemotherapeutic and anti-inflammatory agents. In this study, novel Pt(IV) complexes based on cisplatin and oxaliplatin were synthesized, incorporating non-steroidal anti-inflammatory drugs (NSAIDs) and their carboxyl ester analogues. Certain cisplatin-based Pt(IV) complexes 22-30 exhibited increased cytotoxicity in human cancer cell lines compared to the Pt(II) drug. Complex 26, containing two aceclofenac moieties, displayed potent anticancer effects combined with anti-inflammatory properties.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Andreas Gradwohl, Jakob Windisch, Matthias Weissensteiner, Bernhard K. Keppler, Wolfgang Kandioller, Franz Jirsa
Summary: The task-specific ionic liquid trihexyltetradecylphosphonium 3-hydroxy-2-naphthoate is a suitable extraction agent for rare earth elements, achieving high extraction efficacies and minimal precipitation of the metals. The extraction efficiency is influenced by pH, temperature, and extraction time, and anion exchange is the extraction mechanism. The leaching into the used matrices is in line with literature values and is not significantly affected by temperature.
Article
Chemistry, Inorganic & Nuclear
Thomas Maier, Judith Wutschitz, Natalie Gajic, Michaela Hejl, Klaudia Cseh, Sebastian Mai, Michael A. Jakupec, Mathea S. Galanski, Bernhard K. Keppler
Summary: This study analyzed the unexpected reaction of (1R,2R)-(cyclohexane-1,2-diamine)dichloridoplatinum(II) with maleic acid and synthesized a series of derivatives with different lipophilicity. The results showed low cytotoxicity and no interaction with DNA for these compounds, indicating their lower reactivity compared to oxaliplatin.
DALTON TRANSACTIONS
(2023)