Article
Chemistry, Multidisciplinary
Jana Curillova, Maria Pechacova, Tereza Padrtova, Daniel Pecher, Sarka Mascaretti, Josef Jampilek, Ludmila Paskova, Frantisek Bilka, Gustav Kovac, Ivan Malik
Summary: This research focused on the synthesis, analysis, physicochemical evaluation, and biological evaluation of hybrid molecules with specific structures. The molecules showed inhibitory effects on mycobacteria and were also tested for toxicity on human liver cancer cells. However, some molecules also exhibited toxicity on normal cells.
APPLIED SCIENCES-BASEL
(2022)
Article
Chemistry, Organic
Ol'ga A. Tarasova, Marina A. Maximova, Alexander Albanov, Nina A. Nedolya, Boris A. Trofimov
Summary: Deprotonative metalation of N-isopropenyl-1H-pyrroles with superbases followed by trapping with a variety of electrophiles has been studied as an effective method for the regioselective functionalization of 1H-pyrroles.
SYNTHESIS-STUTTGART
(2022)
Article
Biochemistry & Molecular Biology
Estevao Silveira Grams, Alessandro Silva Ramos, Mauro Neves Muniz, Raoni S. Rambo, Marcia Alberton Perello, Nathalia Sperotto, Laura Calle Gonzalez, Lovaine Silva Duarte, Luiza Galina, Adilio Silva Dadda, Guilherme Arrache Goncalves, Cristiano Valim Bizarro, Luiz Augusto Basso, Pablo Machado
Summary: By synthesizing and evaluating a series of compounds, it was found that two of them exhibited similar antibacterial effects to isoniazid and showed no significant toxicity to host cells. The chemical stability and permeability of these compounds were also assessed.
Article
Chemistry, Multidisciplinary
Benjamin Goka, Douglas A. Klumpp
Summary: We have developed a procedure for the Michael addition of 4-hydroxycoumarins to vinyl-substituted N-heterocycles, which is also suitable for thiocoumarins and quinolinones. A proposed mechanism involves nucleophilic attack at the vinyl-group of the protonated N-heterocycle.
Article
Chemistry, Multidisciplinary
Wande Zhang, Shiqiang Wei, Wenyao Wang, Jingping Qu, Baomin Wang
Summary: An organocatalytic asymmetric process was reported for the construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements with high yield and excellent diastereoselectivity and enantioselectivity. The process features mild reaction conditions, simple operation, broad substrate scope, and good practicability as demonstrated by gram-scale reactions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Ryu Yamasaki, Mariko Ono, Kento Morita, Ai Ito, Kazuo Fukuda, Iwao Okamoto
Summary: Methyl substitution at the double bond of N-alkenyl anilides affects both the preferred conformation and susceptibility to acidic hydrolysis. Substitution at the R-1 position favors the trans conformation, while substitution at the R-2 or R-3 position favors the cis conformation. Substitution at the R-1 and R-3 positions increases the ratio of the trans conformer. DFT study reveals that these conformational preferences can be explained by torsion twisting induced by the substituent on the N-alkenyl moiety relative to the amide plane. R-1 substitution enhances susceptibility to acidic hydrolysis, while R-2 or R-3 substitution increases stability. The effect of the double bond on conformational preferences is demonstrated by comparing the preferred conformation of R-1-substituted anilide (trans) and hydrogenated N-isopropyl amide (cis).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Zhibing Wu, Hyung-Yeon Park, Dewen Xie, Jingxin Yang, Shuaitao Hou, Nasir Shahzad, Chan Kyung Kim, Song Yang
Summary: This study investigated a series of novel SDH inhibitors for their antifungal activity against phytopathogenic fungi, showing that some compounds exhibited excellent antifungal activity. Experiment results further revealed that these compounds might work by targeting SDH.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Pharmacology & Pharmacy
Ahad Amer Alsaiari, Mazen M. Almehmadi, Mohammad Asif
Summary: A series of novel N-Arylidene-4-(4-nitro-1H-benzo[d]imidazol-2-yl)aniline derivatives were synthesized and characterized. In vitro antimycobacterial activity was evaluated against M. tuberculosis H37Rv using the Microplate Alamar Blue dye Assay technique. The compounds showed weak antimycobacterial action, and the relationship between biological activity and functional group variation was discussed.
LATIN AMERICAN JOURNAL OF PHARMACY
(2023)
Article
Chemistry, Multidisciplinary
Sona Krajcovicova, Jan Hlavac, Kristyna Vychodilova
Summary: This study presents a fast and simple method for accessing N-arylated 3-hydroxyquinolin-4(1H)-ones starting from easily available 1-methyl-2-iodoterephthalate and variously substituted anilines. N-Alkylated anthranilic acid derivatives are important intermediates and can be prepared advantageously by solid-phase synthesis, Buchwald-Hartwig amination, or reductive amination with wide substrate scope and excellent crude purities.
Article
Chemistry, Organic
Liu-Liang Mao, An-Xi Zhou, Xian-Hong Zhu, Huanan Peng, Li-Xia Quan, Jie-Ping Wan, Shang-Dong Yang
Summary: We have developed an efficient and facile visible-light-mediated tandem difluoromethylation/cyclization of alkenyl aldehydes using easily accessible and air-stable [Ph3PCF2H]Br-+(-) as the difluoromethylation reagent. Various CF2H-substituted chroman-4-one skeletons and their derivatives are efficiently produced in moderate to good yields with excellent chemoselectivity under mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Lyaysan R. Latypova, Gulsum S. Usmanova, Liliya Ya. Vasilova, Anastasia N. Andriianova, Samil M. Salikhov, Vladimir V. Zorin, Akhat G. Mustafin
Summary: Polyaniline derivatives containing alkyl and alkenyl fragments were synthesized and characterized. The chemical structures of the polymers were analyzed using NMR, UV-Vis, and FT-IR. SEM images showed different shapes and surface morphology of the polymers. The N-alkenyl PANIs exhibited higher stability and better antibacterial activities against both gram-positive and gram-negative bacteria, making them potential candidates for biomedical applications.
JOURNAL OF POLYMER RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Shichao Li, Muyao Li, Shu-Sen Li, Jianbo Wang
Summary: A palladium-catalyzed stereoselective synthesis method has been developed for obtaining trans-alkenyl MIDA boronates from N-Methyliminodiacetyl boronate (BMIDA)-substituted N-tosylhydrazone and benzyl bromides. The products show moderate yields and good functional group compatibility, with potential applications in the synthesis of other boron-containing compounds or in cross-coupling reactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Mohammed B. Alshammari, Mohamed Ramadan, Ashraf A. Aly, Essmat M. El-Sheref, Md Afroz Bakht, Mahmoud A. . A. . Ibrahim, Ahmed M. Shawky
Summary: A new series of synthesized N-substituted-2-quinolonylacetohydrazides were evaluated for their activity towards SARS-CoV-2, with their structures confirmed by NMR, mass, IR spectra, and elemental analysis. Molecular docking calculations showed that most of the compounds had good binding affinity to the SARS-CoV-2 main protease (M-pro) comparable to Remdesivir.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Li Chen, Yuan-Da Li, Ying Lv, Zi-Han Lu, Sheng-Jiao Yan
Summary: A novel method was developed for the one-step synthesis of functionalized CMPOs, allowing for combinatorial and parallel syntheses.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Daniel Borecki, Matthias Lehr
Summary: The structural modification of the sulfamoylbenzoic acid derivative was performed to increase its inhibitory potency against cytosolic phospholipase A(2)alpha (cPLA(2)alpha). Only compounds with strong structural convergence to the potent benzhydrylindole-substituted benzoic acid derivatives showed considerable potency.
MEDICINAL CHEMISTRY RESEARCH
(2022)
Article
Neurosciences
Robin Visvanathar, Maria Papanikolaou, Diana Aline Noga, Marina Padua-Reis, Adriano Bretanha Lopes Tort, Martina Blunder
Summary: The field of cannabinoid research is gaining increasing interest, with a focus on the function of cannabinoids within the CNS. While Cb-1 receptors have been extensively studied, recent attention has shifted towards Cb-2 receptors in the brain, which remain largely unexplored. Through studies on hippocampal Cb(2)Rs, significant progress has been made in understanding their role in modulating cellular properties and network excitability, challenging prior notions of the endocannabinoid system. Targeting hippocampal Cb(2)Rs may offer novel therapies for memory and adult neurogenesis deficits.
REVIEWS IN THE NEUROSCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Birgit Lohberger, Heike Kaltenegger, Nicole Eck, Dietmar Glaenzer, Patrick Sadoghi, Andreas Leithner, Rudolf Bauer, Nadine Kretschmer, Bibiane Steinecker-Frohnwieser
Summary: This study investigated the effects of shikonin derivatives on inflammation, MMP expression, and MAPK signaling in healthy and osteoarthritis chondrocytes. The results demonstrate that shikonin can reduce the inflammatory response and affect downstream regulation, potentially providing a therapeutic approach for osteoarthritis.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Nadine Kretschmer, Christin Durchschein, Antje Hufner, Beate Rinner, Birgit Lohberger, Rudolf Bauer
Summary: In this study, a novel shikonin derivative called SK119 was synthesized and evaluated for its pharmacological effects on human melanoma cells. SK119 exhibited promising activity in a nano-molar range and showed synergistic effects with vemurafenib and cobimetinib, two clinically used melanoma therapeutics. Further research indicates the potential of SK119 in melanoma therapy.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Biographical-Item
Plant Sciences
Rudolf Bauer
PHARMACEUTICAL BIOLOGY
(2022)
Article
Chemistry, Medicinal
Maren Eggers, Peggy Jungke, Volker Wolkinger, Rudolf Bauer, Uwe Kessler, Bruno Frank
Summary: Respiratory viruses are a significant threat to global health. Plant-derived products such as black chokeberry, pomegranate juice, and green tea have been found to have strong antiviral activity against SARS-CoV-2 and IAV, suggesting their potential in reducing viral loads and preventing viral transmission.
PHYTOTHERAPY RESEARCH
(2022)
Review
Nutrition & Dietetics
Eva-Maria Pferschy-Wenzig, Manuela R. Pausan, Karin Ardjomand-Woelkart, Stefanie Roeck, Ramy M. Ammar, Olaf Kelber, Christine Moissl-Eichinger, Rudolf Bauer
Summary: This systematic review identified and reviewed clinical evidence supporting the use of medicinal plants for the treatment of mental disorders and their interactions with the gut microbiota. The findings suggest that some medicinal plants have the potential to benefit mental health through their interaction with the microbiome-gut-brain axis, but more studies are needed to evaluate their effects on MGBA-related pathways.
Article
Biochemistry & Molecular Biology
Eva-Maria Pferschy-Wenzig, Sabine Ortmann, Atanas G. Atanasov, Klara Hellauer, Juergen Hartler, Olaf Kunert, Markus Gold-Binder, Angela Ladurner, Elke H. Heiss, Simone Latkolik, Yi-Min Zhao, Pia Raab, Marlene Monschein, Nina Trummer, Bola Samuel, Sara Crockett, Jian-Hua Miao, Gerhard G. Thallinger, Valery Bochkov, Verena M. Dirsch, Rudolf Bauer
Summary: This study aimed to detect potentially anti-inflammatory active constituents in ethanolic extracts of Chinese Lonicera species. The results showed that Lonicera species could serve as a source of anti-inflammatory active constituents, although some compounds also impaired cell viability.
Article
Plant Sciences
Tijana Micovic, Jelena S. Katanic Stankovic, Rudolf Bauer, Xuehong Nost, Zoran Markovic, Dejan Milenkovic, Vladimir Jakovljevic, Marina Tomovic, Jovana Bradic, Danijela Stesevic, Danilo Stojanovic, Zoran Maksimovic
Summary: The study found that hyssop herb has anti-inflammatory properties, making it a potential treatment option for inflammatory diseases. The extracts from hyssop herb showed significant inhibition of COX-2 enzyme in in vitro testing and demonstrated anti-inflammatory effects in in vivo testing. Preliminary in silico testing also showed that the organic acids in hyssop herb had better inhibitory activity against COX-1 and COX-2 enzymes compared to common non-steroidal anti-inflammatory drugs.
JOURNAL OF ETHNOPHARMACOLOGY
(2022)
Article
Plant Sciences
Nadine Kretschmer, Christin Durchschein, Guenther Heubl, Eva-Maria Pferschy-Wenzig, Olaf Kunert, Rudolf Bauer
Summary: The precise identification of plant material is essential for rational phytotherapy. Misidentification, as seen in the case of the Chinese medicinal herb Zicao, can lead to significant health risks. Therefore, an urgent need for an accurate identification method is evident.
Article
Biochemistry & Molecular Biology
Jelena Katanic S. Stankovic, Jelena Dorovic Jovanovic, Danijela Misic, Uros Gasic, Stefanie Nikles, Zoran Markovic, Rudolf Bauer
Summary: R. holostea is a medicinal plant with antioxidant, antimicrobial, and anti-inflammatory properties. It contains phenolic acids, flavonoids, and flavonoid glucosides as its main constituents. It is widely distributed in Europe, Western Asia, and North Africa, and was previously used in salads or for the treatment of inflammatory disorders.
Article
Plant Sciences
Huyen Thi Tran, Nadine Kretschmer, Loi Huynh, Rudolf Bauer
Summary: Three carvotacetones isolated from Sphaeranthus africanus were tested against 60 cancer cell lines. Compound 1 showed the highest activity, inducing complete cell death in ACHN and UO-31 renal cancer cells. Compound 2 exhibited strong inhibitory effects on SK-MEL-5 melanoma and ACHN renal cancer cells, while compound 3 showed strong growth inhibitory effects on renal cancer cells.
Article
Plant Sciences
Teresa Pirker, Eva-Maria Pferschy-Wenzig, Evangelia Bampali, Valery Bochkov, Rudolf Bauer
Summary: The study aimed to investigate the anti-inflammatory properties of Osmanthus fragrans flowers and characterize their active principles and mechanisms of action. The results demonstrate the anti-inflammatory potential of the flower extracts, especially the glycolipid-enriched fraction, which may mediate its effects by inhibiting the TLR4 receptor complex.
JOURNAL OF ETHNOPHARMACOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Werner Seebacher, Michael Hoffelner, Ferdinand Belaj, Teresa Pirker, Muaaz Alajlani, Rudolf Bauer, Eva-Maria Pferschy-Wenzig, Robert Saf, Robert Weis
Summary: In this study, various 4-aminotetrahydropyridinylidene salts were reacted with aldehydes under alkaline conditions. The reaction successfully yielded 5-substituted beta-hydroxyketones only when aliphatic aldehydes were used. When aromatic aldehydes were used, 5-substituted beta-aminoketones or a single delta-diketone were obtained. The new compounds were characterized using spectroscopic methods and single crystal structure analysis, and some of them exhibited anticancer and antibacterial properties.
Article
Biochemistry & Molecular Biology
Eva-Maria Pferschy-Wenzig, Olaf Kunert, Timo Thumann, Christine Moissl-Eichinger, Rudolf Bauer
Summary: Silymarin, a mixture of flavonolignans from milk thistle fruits, has various pharmacological activities. However, its oral bioavailability is limited due to low water solubility and extensive metabolism. The study investigated the biotransformation of silymarin by gut microorganisms and identified multiple metabolites, including demethylation products and low molecular weight aromatic metabolites. The potential pharmacological activities of these gut microbial metabolites warrant further examination.
Article
Plant Sciences
R. M. Ammar, E. M. Pferschy-Wenzig, P. Van den Abbeele, L. Verstrepen, J. Ghyselinck, T. Thumann, R. Bauer
Summary: This study assessed the bidirectional interactions between STW 5-II and the human gut microbiome. The results showed that STW 5-II promoted the growth of beneficial bacteria and inhibited the growth of pathogenic bacteria. In addition, STW 5-II improved gut barrier function and had anti-inflammatory effects. These findings suggest that STW 5-II has a regulatory effect on gut health.
Article
Chemistry, Medicinal
Shuang Mei, Su Jiang, Yuting Wang, Han Jing, Peng Yang, Miao-Miao Niu, Jindong Li, Kai Yuan, Yan Zhang
Summary: This study identifies a dual-targeting peptide, AP-1, that effectively inhibits variants of concern (VOCs) of SARS-CoV-2 without impairing host cell viability. The findings suggest that AP-1 could be a promising broad-spectrum agent for treating emerging VOCs of SARS-CoV-2.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Hyeonjun Lee, Ju Yeon Lee, Hyunsoo Jang, Hye Young Cho, Minhee Kang, Sang Hyun Bae, Suin Kim, Eunji Kim, Jaebong Jang, Jin Young Kim, Young Ho Jeon
Summary: By using liquid chromatography-tandem mass spectrometry and nuclear magnetic resonance experiments, we identified new chemical moieties that bind to the target sites of the protein of interest, allowing for reversible binding and protein degradation. This method has the potential to expand the application of PROTAC technology.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Yingying Li, Xiyou Du, Xinru Kong, Yuelin Fang, Zhijing He, Dongzhu Liu, Hang Wu, Jianbo Ji, Xiaoye Yang, Lei Ye, Guangxi Zhai
Summary: This study proposes a novel nanoplatform based on the autophagy cascade to overcome the obstacles in chemo-immunotherapy. The platform combines chemotherapy and starvation therapy to initiate pro-death autophagy and enhance antigen presentation, while also remodeling the immunosuppressive tumor microenvironment. Furthermore, the study discovers a new therapeutic direction for the respiration inhibitor 3-bromopyruvic acid (3BP) in cancer treatment. Overall, this study offers an opportunity to improve antitumor efficacy and boost immune responses.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Bingsi Wang, Mingxu Ma, Yusen Dai, Pengfei Yu, Liang Ye, Wenyan Wang, Chunjie Sha, Huijie Yang, Yingjie Yang, Yunjing Zhu, Lin Dong, Shujuan Wei, Linlin Wang, Jingwei Tian, Hongbo Wang
Summary: Breast cancer is a common malignant tumor in women, and drug resistance remains a clinical challenge. In this study, a novel compound, G-5b, was developed with potent antagonistic and degradation activities comparable to the current drug fulvestrant. G-5b also showed improved stability and solubility. Mechanistically, G-5b engages the proteasome pathway to degrade ER, inhibiting the ER signaling pathway and inducing apoptosis and cell cycle arrest. In animal models, G-5b exhibited superior pharmacokinetics and pharmacodynamics properties. Overall, G-5b is a promising long-acting SERD worthy of further investigation and optimization.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Karoline B. Waitman, Larissa C. de Almeida, Marina C. Primi, Jorge A. E. G. Carlos, Claudia Ruiz, Thales Kronenberger, Stefan Laufer, Marcia Ines Goettert, Antti Poso, Sandra V. Vassiliades, Vinicius A. M. de Souza, Monica F. Z. J. Toledo, Neuza M. A. Hassimotto, Michael D. Cameron, Thomas D. Bannister, Leticia Costa-Lotufo, Joa o A. Machado-Neto, Mauricio T. Tavares, Roberto Parise-Filho
Summary: A series of hybrid inhibitors combining pharmacophores of known kinase inhibitors and benzohydroxamate HDAC inhibitors were synthesized and evaluated for their anticancer activity and pharmacokinetic properties. Compounds 4d-f exhibited promising cytotoxicity against hematological cells and moderate activity against solid tumor models. Compound 4d showed potent inhibition of multiple kinase targets and had stable interactions with HDAC and members of the JAK family. These compounds showed selective cytotoxicity with minimal effects on non-tumorigenic cells and favorable pharmacokinetic profiles.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Michal Sulik, Diana Fontinha, Dietmar Steverding, Szymon Sobczak, Michal Antoszczak, Miguel Prudencio, Adam Huczynski
Summary: This study describes the synthesis of the first-in-class ivermectin derivatives obtained through derivatization of the C13 position, along with the unexpected rearrangement of the macrolide ring. These derivatives show potential for antiparasitic activity and are important for the development of new antiparasitic agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Jun Liu, Qiu-Xian Chen, Wen-Fu Wu, Dong Wang, Si -Yu Zhao, Jia-Hao Li, Yi-Qun Chang, Shao-Gao Zeng, Jia-Yi Hu, Yu-Jie Li, Jia-Xin Du, Shu-Meng Jiao, Hai-Chuan Xiao, Qiang Zhang, Jun Xu, Jian-Fu Zhao, Hai -Bo Zhou, Yong-Heng Wang, Jian Zou, Ping-Hua Sun
Summary: A new anti-infective drug strategy has been discovered to attenuate virulence and modulate inflammation caused by drug-resistant Pseudomonas aeruginosa infections. Compound 5f inhibits biofilm formation, macrophage migration, and inflammatory response induced by P. aeruginosa, showing potential as a novel candidate against drug-resistant infections.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Liuzeng Chen, Ke Wang, Lingyun Wang, Wei Wang, Lifan Wang, Jia Li, Xiaohan Liu, Mengya Wang, Banfeng Ruan
Summary: In this study, a series of novel anti-inflammatory compounds were designed and synthesized based on the natural product pterostilbene skeleton. Among them, compound 8 showed the highest activity and exhibited its effects through inhibition of pro-inflammatory cytokines by blocking the NF-KB/MAPK signaling pathway. Compound 8 also demonstrated a good relieving effect on acute colitis in mice and showed good safety in acute toxicity experiments.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Si-Min Liang, Gui-Bin Liang, Hui-Ling Wang, Hong Jiang, Xian-Li Ma, Jian-Hua Wei, Ri-Zhen Huang, Ye Zhang
Summary: A series of novel multi-target antitumor agents were designed, synthesized, and evaluated. Some compounds exhibited significant antitumor activity and one compound showed excellent efficacy, limited toxicity, and low resistance. Further mechanism studies revealed that the compound exerted antitumor effects through multiple pathways.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)