Article
Polymer Science
Cheng Tang, Wenwen Yang, Zhijuan Zou, Fang Liao, Chunmei Zeng, Kunpeng Song
Summary: In this study, a facile and eco-friendly in situ assembly technique was used to produce a PdFe bimetallic hyper-crosslinked polymer catalyst for the Ullmann reaction. The catalyst exhibited a hierarchical pore structure, high specific surface area, and uniform distribution of active sites, which resulted in high catalytic activity and stability. The exceptional catalytic performance of the catalyst was attributed to its robust absorption capability, high dispersion, and strong interaction between Fe and Pd.
Article
Chemistry, Organic
Zhuo-Huan Li, Yi-Chun Wang, Tuan-Jie Li, Jian-Quan Liu, Xiang-Shan Wang
Summary: 2,3-Bisaryldiimidazo [1,2-a:1',2'-c]quinazolines were successfully synthesized via a copper-catalyzed reaction, with good yields. This reaction employed a double Ullmann cross-coupling to build two new Csp(2)-N bonds in one-pot procedure, resulting in the formation of a tetracyclic heterocycle bearing four nitrogen atoms.
Article
Chemistry, Organic
Ban Van Phuc, Quang Huy Dinh, Nguyen Linh Chi, Quyet Tien Nguyen, Nguyen Van Tuyen, Hien Nguyen, Peter Langer, Tuan Thanh Dang, Tran Quang Hung
Summary: Fluorescent active small molecules containing 5H-pyrido [12',1':2,3]imidazo [4,5-b]indole core were successfully synthesized via Cu-catalyzed double C-N coupling reaction from 3-bromo-2-(2-bromophenyl) imidazo [1,2-a]pyridine with various amines in high yields. DMSO, a green solvent, played a crucial role in the success of this reaction. This method has potential applications in pharmaceutical chemistry and materials science.
Review
Biochemistry & Molecular Biology
Ivar von Kuegelgen
Summary: P2Y receptors are G-protein-coupled receptors for extracellular nucleotides. There are eight mammalian P2Y receptor subtypes that play important roles in physiology and pathophysiology. This review summarizes the use of pharmacological tools to characterize the P2Y receptor subtypes involved in these responses.
PURINERGIC SIGNALLING
(2023)
Article
Chemistry, Multidisciplinary
Zhimei Mao, Aimin Huang, Lin Ma, Min Zhang
Summary: A facile visible light-promoted approach has been developed for the synthesis of anthracenone-furans from readily available 2,3-dibromonaphthoquinones and phenylbenzofurans via a formal Diels Alder reaction. This reaction involves wavelength-selective agitation of 4CzIPN, energy transfer to quinones, recombination of 1,6-biradicals, and elimination to give anthracenone-furans in good to excellent yields in one pot.
Article
Chemistry, Organic
Kaustubh U. Jagushte, Rohit N. Ketkar, Chinmay Thakkar, Sharmistha Dutta Choudhury, Nabanita Sadhukhan
Summary: In this study, a strategic approach was used to synthesize 6-amino-2-naphthol with high efficiency and consistent yield. Two protocols, direct amination and a cascade synthetic approach, were explored. Through extensive method optimization, a superior catalyst combination was discovered, making the synthesis of 6-amino-2-naphthol simple, sustainable, efficient, and with consistent yield.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Zheng Sonia Lin, Benoit H. Lessard, Jaclyn Brusso
Summary: Fluorinated compounds have gained attention for their small size and strong electron-withdrawing property. In materials science, perfluorinated polyphenylenes are important in organic electronics as electron transport layers. However, the synthesis of perfluorinated arenes is limited due to changes in reactivity upon the introduction of additional fluorine atoms. This article describes the one-step synthesis of a dendrimer perfluoro-3,3'5,5'-tetrakisphenyldiphenyl-1,1' and the synthetic methodology for the direct preparation of linear perfluorinated para-sexiphenyl, using commercially available or easily accessible starting materials.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Jinping Hu, Zhaofeng Liang, Hongbing Wang, Huan Zhang, Chaoqin Huang, Lei Xie, Zheshen Li, Zheng Jiang, Han Huang, Fei Song
Summary: On-surface Ullmann coupling has been a focus due to its unique fabrication of conjugated nanostructures with high controllability. The symmetrical dehalogenation of Br2Py on Cu(111) has been studied in detail using a combination of techniques, revealing the formation of OM chains and interesting patterns at different temperatures. The construction of covalent organic chains from different OM intermediates after annealing provides insight into surface Ullmann coupling mechanisms.
APPLIED SURFACE SCIENCE
(2021)
Article
Chemistry, Organic
Xiangle Jin, Lidong Xing, Daniel Da Deng, Jun Yan, Yan Fu, Weitong Dong
Summary: This work presents a concise method for synthesizing a wide range of mono- or disubstituted 2-amino isonicotinic acids using 2,4-dioxo-carboxylic acid ethyl esters and ethyl 3-amino-3-iminopropionate hydrochloride. The reaction likely involves an in situ decarboxylation process and bears resemblance to the Guareschi-Thorpe Condensation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Teng Zhang, Renyi Li, Xiaoyu Hao, Quanzhen Zhang, Huixia Yang, Yanhui Hou, Baofei Hou, Liangguang Jia, Kaiyue Jiang, Yu Zhang, Xu Wu, Xiaodong Zhuang, Liwei Liu, Yugui Yao, Wei Guo, Yeliang Wang
Summary: Ullmann-like on-surface synthesis is an appropriate approach for fabricating covalent organic nanostructures. In this study, we used 2D hBN as a protective layer and successfully achieved Ullmann-like coupling of a planar biphenylene-based molecule on an hBN/Rh(111) surface. This finding is expected to be important for high-yield fabrication of functional nanostructures for future information devices.
Article
Chemistry, Organic
Bhawyanth Duvvuru, Dinara Amankulova, Sebastien Gauden, Theo Haffemayer, Derrick L. J. Clive
Summary: Meta-(aryloxy)phenols are synthesized by the action of DBU on 2-bromo-3-(aryloxy)cyclohex-2-en-1-ones. The starting compounds can be readily obtained from 3-chlorocyclohex-2-en-1-ones through two steps: replacement of chlorine with an aryloxy group and bromination. This method is a mild alternative to the classical Ullmann reaction and does not require any metal catalyst. However, the efficiency of aromatization step is affected by the electronic properties of the substituents on the original phenols.
Article
Chemistry, Organic
Baiyao Zhu, Wenfang Xiong, Xiaobin Tan, Wanqing Wu, Huanfeng Jiang
Summary: A copper-catalyzed Ullmann-type C-N cross-coupling reaction of carbazole with aryl chlorides has been developed using N,N'-bis(thiophene-2-ylmethyl)oxalamide as ligand, which efficiently affords N-arylcarbazole.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
yangyang Sun, Gang Feng, Chao Chen, Yonghong Liu, Xu Zhang
Summary: Cu/polymeric carbon nitride (PCN) prepared by calcining Cu(NO3)(2) with the melamine precursor at 550 degrees C can catalyze the Ullmann-type C-N coupling reactions. The material is more active than traditional Cu(I) and Pd catalysts, offering an opportunity for developing efficient novel catalysts for synthesis of medicines containing pyrimidin-2-amine moieties.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Huamin Wang, Wenjing Niu, Yongjun He, Yibo Wei, Xianxian Li, Ying-Wu Lin
Summary: We report a general and effective system for the cyclization of beta-trifluoromethyl enones with amidines using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as a catalyst. This reaction provides a range of trifluoromethylated 2-imidazolines in high yields and good diastereoselectivities, with good tolerance towards functional groups. Additionally, a one-pot synthesis of trifluoromethylated imidazoles via sequential cyclization and oxidation is demonstrated. The reaction mechanism is verified by ESI-MS studies, confirming a reasonable proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
San L. Pham, Taehee Kim, Frank E. McDonald
Summary: CuI and trans-N,N'-dimethylcyclohexyldiamine catalyze the single-step C-O bond cross-coupling between 1,2-di- and trisubstituted vinylic halides with functionalized alcohols, producing acyclic vinylic ethers. This method selectively gives (E)- and (Z)-vinylic ether products from the corresponding vinyl halide precursors, and is compatible with carbohydrate-derived primary and secondary alcohols and other functional groups. The conditions are mild and do not promote Claisen rearrangements.
Article
Biochemistry & Molecular Biology
Pedro Valada, Sonja Hinz, Christin Vielmuth, Catia R. Lopes, Rodrigo A. Cunha, Christa E. Mueller, Joao Pedro Lopes
Summary: Inosine has neuroprotective effects by indirectly modifying the activity of adenosine receptors and controlling synaptic transmission and plasticity. It acts as a ligand of adenosine receptors with low affinity and shows higher affinity towards the rat A(3) receptor. The impact of inosine on synaptic transmission and plasticity is mediated by modification of extracellular levels of adenosine through equilibrative nucleoside transporters.
PURINERGIC SIGNALLING
(2023)
Article
Chemistry, Medicinal
Andhika B. B. Mahardhika, Anastasiia Ressemann, Sarah E. E. Kremers, Mariana S. Gregorio S. Castanheira, Clara T. T. Schoeder, Christa E. E. Mueller, Thanigaimalai Pillaiyar
Summary: The study synthesized a series of DIM derivatives and evaluated their affinities and efficacies for human CB receptor subtypes. The compound di-(4-cyano-1H-indol-3-yl)methane showed the highest potency as a CB2 receptor agonist and has potential as a novel drug for inflammatory diseases.
ARCHIV DER PHARMAZIE
(2023)
Article
Chemistry, Physical
A. Ramadan Ibrahim, Balqees S. Al -Saadi, John Husband, Ahmed H. Ismail, Younis Baqi, Osama K. Abou-Zied
Summary: Efficient electron injection from the photosensitizer DHC-COOH to TiO2 nanoparticles is achieved, with the involvement of the OH group causing a red shift in the spectra and the COOH group enhancing intramolecular charge transfer. The characterization of the system is carried out by synthesizing and characterizing several derivatives. The findings have implications for applications such as solar energy harvesting and catalytic reactions.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Pharmacology & Pharmacy
Jan H. Voss, Haneen Al-Hroub, Robin Gedschold, Jennifer M. Dietrich, Evelyn Gaffal, Marieta Toma, Stefan Kehraus, Gabriele M. Koenig, Peter Brust, Bernd K. Fleischmann, Daniela Wenzel, Winnie Deuther-Conrad, Christa E. Mueller
Summary: G protein is identified as a potential drug target for treating complex diseases. The development of specific radiotracers allows for disease diagnosis and research.
Article
Biochemistry & Molecular Biology
Chunyang Bi, Laura Schaekel, Salahuddin Mirza, Katharina Sylvester, Julie Pelletier, Sang -Yong Lee, Thanigaimalai Pillaiyar, Jean Sevigny, Christa E. Mueller
Summary: Ticlopidine is an antithrombotic prodrug that inhibits platelet function by covalently blocking the P2Y12 receptor on thrombocytes. It was found that Ticlopidine also inhibits CD39, an enzyme involved in ATP hydrolysis. In this study, a comprehensive analysis of Ticlopidine derivatives was conducted, leading to the discovery of benzotetrahydropyridines as a novel class of allosteric CD39 inhibitors.
BIOORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Malgorzata Frankowska, Karolina Wydra, Agata Suder, Magdalena Zaniewska, Dawid Gawlinski, Joanna Miszkiel, Anna Furgala-Wojas, Kinga Salat, Malgorzata Filip, Christa E. Mueller, Katarzyna Kiec-Kononowicz, Magdalena Kotanska
Summary: This study discovered three novel selective ligands for GPR18, including one agonist and two antagonists. The activation of GPR18 has similar effects to the CB receptor system, impacting emotional behavior, food intake, and pain activity. Therefore, GPR18 represents a potential therapeutic target for mood, pain, and/or eating disorders.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Editorial Material
Chemistry, Medicinal
Jeffrey Aube, Craig W. Lindsley, Christa E. Mueller
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Mariam Tahoun, Marianne Engeser, Luca Svolacchia, Paul Martin Sander, Christa E. E. Mueller
Summary: This study investigates the stability and degradation of the oxygen-complexing prosthetic group of hemoglobin, heme, under various conditions expected to occur during fossilization. The results reveal that heme is most stable under anaerobic reductive conditions and least stable in the presence of H2O2. The presence of oxygen and H2O2 leads to the cleavage of heme and the formation of hematinic acid. The role of iron cation in heme degradation is confirmed, as heme lacking iron remains more stable. This study provides valuable insights into the fate of heme during fossilization.
Editorial Material
Chemistry, Medicinal
Jeffrey Aube, Craig W. Lindsley, Christa E. Mueller
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Multidisciplinary Sciences
Jan H. Voss, Max Cruesemann, Christian R. O. Bartling, Stefan Kehraus, Asuka Inoue, Gabriele M. Koenig, Kristian Stromgaard, Christa E. Mueller
Summary: This study investigated the inhibitory effects of macrocyclic depsipeptides YM-254890 and FR900359 on Gaq/11 proteins and observed significant differences in dissociation kinetics between these compounds and their hydrogenated, tritium-labeled derivatives. Results showed that small structural modifications had a major impact on the residence time of the macrocyclic depsipeptides. FR exhibited pseudo-irreversible binding, while YM had a faster dissociation rate. The isopropyl anchor in FR and some derivatives was found to be essential for slow dissociation. These findings provide a basis for future drug design strategies to modulate residence times of macrocyclic Gq protein inhibitors, which play a crucial role in therapeutic outcomes.
Article
Chemistry, Multidisciplinary
Tobias Claff, Jonathan G. Schlegel, Jan H. Voss, Victoria J. Vaassen, Renato H. Weisse, Robert K. Y. Cheng, Sandra Markovic-Mueller, Denis Bucher, Norbert Straeter, Christa E. Mueller
Summary: The authors report the crystal structures of A(2A)AR in complex with Etrumadenant, revealing a previously unknown interaction. These findings have implications for the design of selective receptor antagonists.
COMMUNICATIONS CHEMISTRY
(2023)
Editorial Material
Chemistry, Medicinal
Jeffrey Aube, Craig W. Lindsley, Christa E. Mueller
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2023)
Article
Biochemistry & Molecular Biology
Michal Zaluski, Tadeusz Karcz, Anna Drabczynska, Christin Vielmuth, Agnieszka Olejarz-Maciej, Monika Gluch-Lutwin, Barbara Mordyl, Agata Siwek, Grzegorz Satala, Christa E. Muller, Katarzyna Kiec-Kononowicz
Summary: Multitarget drugs designed with a hybrid dopamine-xanthine core have potential as drug candidates for neurodegenerative diseases. Further development of monoamine oxidase B (MAO-B) inhibitors with A(2A) adenosine receptor (A(2A)AR) antagonistic properties led to additional phosphodiesterase-4 and -10 (PDE4/10) inhibition and/or dopamine D-2 receptor (D2R) agonistic activity. The compounds showed MAO-B inhibition combined with A(2A)AR affinity, and some compounds exhibited enhanced PDE-inhibitory and D2R-agonistic activity through structural modifications. The multitarget drugs also demonstrated antioxidant properties in vitro and neuroprotective effects in a cellular model.
Article
Biochemistry & Molecular Biology
Nina Geiger, Viktoria Diesendorf, Valeria Roll, Eva-Maria Koenig, Helena Obernolte, Katherina Sewald, Julian Breidenbach, Thanigaimalai Pillaiyar, Michael Guetschow, Christa E. Mueller, Jochen Bodem
Summary: Recently, we investigated novel pyridyl indole esters and peptidomimetics as potent inhibitors of SARS-CoV-2 main protease. We analyzed the impact of these compounds on viral replication and found that their effectiveness varied in different cell lines. In Huh-7 cells, the protease inhibitors suppressed viral replication by up to 5 orders of magnitude, while in Calu-3 cells, suppression by 2 orders of magnitude was achieved. Three pyridin-3-yl indole-carboxylates showed antiviral activity in all cell lines and also in human precision-cut lung slices.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Medicinal
Daniel Marx, Mohamed Wessam Alnouri, Sophie Clemens, Robin Gedschold, Yvonne Riedel, Ghazl Al Hamwi, Thanigaimalai Pillaiyar, Jorg Hockemeyer, Vigneshwaran Namasivayam, Christa E. Mueller
Summary: This study discovered a xanthine derivative that activates the main variant of MRGPRX4, and optimization resulted in analogs with high potency and metabolic stability. These compounds are promising tool compounds for exploring the potential of MRGPRX4 as a future drug target.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan
Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang
Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman
Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li
Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang
Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla
Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
