Article
Plant Sciences
Jerald J. Nair, Johannes van Staden
Summary: The alkaloid principles found in the plant family Amaryllidaceae have shown potential antiviral activities against a wide range of pathogens. Their chemical diversity and efficacy against viral families make them promising candidates for antiviral drug discovery.
Article
Chemistry, Organic
Giorgio Rizzo, Gianluigi Albano, Teresa Sibillano, Cinzia Giannini, Roberta Musio, Fiorenzo G. Omenetto, Gianluca M. Farinola
Summary: This paper reports the application of a silk fibroin-supported Palladium catalyst (Pd/SF) in Suzuki-Miyaura and Ullmann coupling reactions of aryl chlorides. The existence of catalytic pockets where monoatomic palladium species can form stable complexes with SF is hypothesized and supported by experimental analysis. The size of the catalytic pocket of Pd/SF is estimated to be approximately 15 angstroms using computational modeling.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Medicine, Research & Experimental
Darja Koutova, Negar Maafi, Darina Muthna, Karel Kralovec, Jana Kroustkova, Filip Pidany, Abdul Aziz Timbilla, Eva Cermakova, Lucie Cahlikova, Martina Rezacova, Radim Havelek
Summary: The isoquinoline alkaloids found in Amaryllidaceae have potential for the development of new drugs. In this study, the cytotoxic activities of montanine and its derivatives were evaluated against multiple cancer cell lines, and it was found that montanine exhibited the most potent antiproliferative activity and induced apoptosis in MOLT-4 cells.
BIOMEDICINE & PHARMACOTHERAPY
(2023)
Article
Chemistry, Applied
Fabienne Hoffmann-Emery, Katrin Niedermann, Pankaj D. Rege, Manuel Konrath, Christian Lautz, Anne Katrin Kraft, Carine Steiner, Fritz Bliss, Andre Hell, Rolf Fischer, Diane E. Carrera, Danial Beaudry, Remy Angelaud, Sushant Malhotra, Francis Gosselin
Summary: A sustainable second-generation process for GDC-0134 was developed to meet the safety and greenness requirements of supplying pivotal clinical studies. The process involved the discovery of alternative solvents and improved reaction conditions, resulting in a significant reduction in process mass intensity and the successful production of a large amount of GDC-0134.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Multidisciplinary Sciences
Arnaud Vanden Broeck, Christophe Lotz, Robert Drillien, Lea Haas, Claire Bedez, Valerie Lamour
Summary: Human type IIA topoisomerases play a crucial role in regulating DNA topology and chromosome organization. The isoform Topo II alpha is a key target for anti-cancer compounds, forming ternary cleavage complexes with DNA. This study provides cryo-EM structures of the entire Topo II alpha nucleoprotein complex, shedding light on the allosteric connections between different domains and the role of the non-conserved C-terminal domain in regulating enzyme activities.
NATURE COMMUNICATIONS
(2021)
Article
Plant Sciences
D. Naidoo, J. C. Manning, L. P. Slavetinska, J. Van Staden
Summary: Isoquinoline alkaloids from the Amaryllidaceae family are valuable in drug discovery, with Distichamine 1 found in Crossyne guttata suggesting wider distribution than originally thought.
SOUTH AFRICAN JOURNAL OF BOTANY
(2021)
Article
Plant Sciences
Amanda Eiriz Feu, Jean Paulo de Andrade, Alejandro Pedro Ayala, Larissa Costa de Almeida, Leticia Costa-Lotufo, Jaume Bastida, Javier Ellena, Warley de Souza Borges
Summary: This study focused on isolating a main alkaloid component from a Brazilian indigenous plant, analyzing its structure through NMR and X-Ray Crystallography, and evaluating its cytotoxic activity against tumor cells.
SOUTH AFRICAN JOURNAL OF BOTANY
(2021)
Article
Plant Sciences
Jerald J. Nair, Johannes van Staden
Summary: Studies have shown that minor alkaloid groups in the Amaryllidaceae plant family have potential anti-cancer effects, with montanine and cripowellin groups demonstrating high antiproliferative activities. Despite their challenging molecular architectures, minor alkaloid groups can be adjusted structurally for target studies. Additionally, parent alkaloids are generally more effective cytotoxic agents than their corresponding semisynthetic derivatives.
Article
Biochemistry & Molecular Biology
Lorene Coelho Silva, Amabel Fernandes Correia, Joao Victor Dutra Gomes, Wanderson Romao, Larissa Campos Motta, Christopher William Fagg, Perola Oliveira Magalhaes, Damaris Silveira, Yris Maria Fonseca-Bazzo
Summary: This study evaluated the antifungal effects of two crude extracts of Crinum americanum L. on Candida species and found that these extracts have antifungal activity. The results are important for the development of new antifungal drugs.
Article
Microbiology
Seydou Ka, Natacha Merindol, Aissatou Aicha Sow, Amita Singh, Karima Landelouci, Melodie B. Plourde, Genevieve Pepin, Marco Masi, Roberta Di Lecce, Antonio Evidente, Matar Seck, Lionel Berthoux, Laurent Chatel-Chaix, Isabel Desgagne-Penix
Summary: The study found that Amaryllidaceae alkaloids (AAs) from plants of the Amaryllidaceae family have strong antiviral activity, with cherylline specifically inhibiting dengue virus and Zika virus replication. This suggests that AAs, including cherylline, could be a potential source of new antiviral drugs.
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY
(2021)
Article
Plant Sciences
Marilu Roxana Soto-Vasquez, Cecilia Anataly Rodriguez-Munoz, Luciana R. Tallini, Jaume Bastida
Summary: This study identified the alkaloid composition and bioactive potential of an extract from the endemic Peruvian plant species Ismene amancaes. The extract contained lycoramine and exhibited inhibitory activity against enzymes and the Plasmodium falciparum strain FCR-3.
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
Kyung-Hwa Jeon, Seojeong Park, Hae Jin Jang, Soo-Yeon Hwang, Aarajana Shrestha, Eung-Seok Lee, Youngjoo Kwon
Summary: The study revealed that AK-I-190, a novel topoisomerase II inhibitor, exerts potent inhibitory activity by intercalating into DNA without stabilizing the DNA-enzyme cleavage complex, resulting in less DNA toxicity compared to etoposide. AK-I-190 induces G1 arrest and effectively inhibits cell proliferation and colony formation in an androgen receptor-negative CRPC cell line, indicating the potential clinical relevance of topoisomerase II catalytic inhibitors in treating this type of prostate cancer.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Biochemistry & Molecular Biology
Dawei Li, Xiyu Chen, Rumeng Yan, Zeshan Jiang, Bing Zhou, Bei Lv
Summary: It was found that oligodeoxynucleotides (ODNs) containing G-quadruplexes can efficiently inhibit the activity of DNA topoisomerase I. Among them, the parallel propeller-type G-quadruplex is the most effective inhibitor. Combining G-quadruplexes with duplexes to form hybrids can enhance the inhibition efficiency. Moreover, a circular ODN with a G-quadruplex motif and DNA topoisomerase I binding site showed high inhibitory efficiency.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Chemistry, Organic
Petr Jansa, Ivana Cisarova, Eliska Matousova
Summary: This study synthesized analogues of bioactive Amaryllidaceae alkaloids with a five-membered ring C and a quaternary carbon center. The synthesis was carried out by closing a new heterocyclic ring B in different ways to obtain products with structural cores of naturally occurring alkaloids. The importance of this study lies in providing a synthetic approach to multiple structural types of potentially bioactive molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yuan-Ye Jhang, Tai-Ting Fan-Chiang, Jun-Min Huang, Jen-Chieh Hsieh
Article
Chemistry, Multidisciplinary
Wei-Lin Chen, Yuan-Ye Jhang, Jen-Chieh Hsieh
RESEARCH ON CHEMICAL INTERMEDIATES
(2017)
Article
Chemistry, Organic
Jen-Chieh Hsieh, Ya-Chun Hong, Chun-Ming Yang, Subramaniyan Mannathan, Chien-Hong Cheng
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Physical
Min-Hsien Chen, Jen-Chieh Hsieh, Yi-Hsien Lee, Chien-Hong Cheng
Article
Chemistry, Organic
Li-Hsuan Yeh, Hung-Kai Wang, Gangaram Pallikonda, Yu-Lun Ciou, Jen-Chieh Hsieh
Review
Chemistry, Organic
Jen-Chieh Hsieh, Haw-Lih Su
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Organic
Vijaykumar H. Thorat, Jen-Chieh Hsieh, Chien-Hong Cheng
Review
Chemistry, Multidisciplinary
Jen-Chieh Hsieh
Summary: This article describes the research on transition-metal-catalyzed cyclization reactions, focusing on four types of coupling reactions for efficient synthesis of N-containing aromatic heterocycles. These methods can be applied to the synthesis of relevant natural alkaloids and biologically active compounds.
Article
Biochemistry & Molecular Biology
Hasil Aman, Yu-Chiao Huang, Yu-Hao Liu, Yu-Lin Tsai, Min Kim, Jen-Chieh Hsieh, Gary Jing Chuang
Summary: A novel synthetic pathway has been developed for the synthesis of 3-(imino)isoindolin-1-ones through Co-catalyzed cyclization reaction, tolerating various substituents and providing moderate yields in most cases. The proposed reaction mechanism involves the formation of a five-membered aza-cobalacycle complex and subsequent nucleophilic addition and substitution reactions to yield the desired structures.
Article
Chemistry, Organic
Vijaykumar H. Thorat, Yu-Lin Tsai, Yong-Ran Huang, Chien-Hong Cheng, Jen-Chieh Hsieh
Summary: In this study, a nickel-catalyzed cyclization reaction was reported, which allowed the generation of polysubstituted biaryl sultams by reacting 1,2,3,4-benzothiatriazine-1,1-dioxides with arynes. The reaction exhibited high tolerance towards substituents on every subunit. Mechanistic investigation revealed the formation of a diradical intermediate, which reacted with a nickel complex to form a nickelacycle intermediate and underwent subsequent cyclization through aryne insertion.
Article
Chemistry, Organic
Vijaykumar H. Thorat, Jen-Chieh Hsieh
Summary: Here, we report a new nickel-catalyzed reaction that allows for the intramolecular denitrogenative dual annulation of aryl nitrile-containing 1,2,3-benzotriazine-4(3H)-ones, leading to the synthesis of polycyclic pyrroloquinazolinones. This reaction demonstrates a high tolerance towards a wide variety of substituents and can serve as a critical step in the synthesis of luotonin A, showcasing its high step economy.
Article
Chemistry, Organic
Vijaykumar H. Thorat, Hasil Aman, Yu-Lin Tsai, Gangaram Pallikonda, Gary Jing Chuang, Jen-Chieh Hsieh
Summary: This study explores the co-catalyzed reactions of 2-halobenzamides and alkynes to form isoquinolones or 2-vinyl benzamides, with the formation of selective products controlled by ligands. The mechanism study reveals that these reactions proceed through different pathways, involving radical processes and two-electron transfer activation of the C-X bond.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Hung-Kai Wang, Yu-Lun Chio, Gangaram Pallikonda, Hsyueh-Liang Wu, Haw-Lih Su, Jen-Chieh Hsieh
Article
Chemistry, Multidisciplinary
Jen-Chieh Hsieh, Yi-Hua Chu, Krishnamoorthy Muralirajan, Chien-Hong Cheng
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
