Pub Date : 2025-02-08DOI: 10.1016/j.tet.2025.134521
Marzieh Enjilzadeh, Ali Keivanloo, Mohammad Bakherad
New hybrid compounds, including imidazo[1,2-a]pyrimidin-2-yl(3-(substituted)quinoxalin-2-yl)methanone and its imidazo[1,2-a]pyridine analogs, have been successfully prepared via palladium-catalyzed reactions. The synthesis involved the reaction of 3-substituted-2-chloroquinoxalines with 2-amino-1-(prop-2-yn-1-yl)pyrimidinium/pyridinium bromide under optimized reaction conditions. These conditions included Pd(PPh3)2Cl2 (5 mol %), CuI (10 mol%) in the presence of Et3N in DMF at 70 °C, resulting in the formation of the desired hybrid compounds. Furthermore, imidazo[1,2-a]pyridine hybrid compounds were synthesized through one-pot multicomponent reactions of 2,3-dicholoroquinoxaline, 2-amino-1-(prop-2-yn-1-yl)pyridinium bromide, primary and secondary amines, under optimized conditions. These processes provided efficient protocols to synthesize novel imidazo[1,2-a]pyrimidine/pyridine based on quinoxaline through palladium-catalyzed reaction with high yields. A one-pot reaction, high reaction yields, energy efficiency, and a straightforward reaction process are significant advantages of this protocol.
{"title":"Synthesis of new hybrid compounds of imidazo[1,2-a]pyrimidine/pyridine based on quinoxaline through palladium-catalyzed coupling reactions and heteroannulation","authors":"Marzieh Enjilzadeh, Ali Keivanloo, Mohammad Bakherad","doi":"10.1016/j.tet.2025.134521","DOIUrl":"10.1016/j.tet.2025.134521","url":null,"abstract":"<div><div>New hybrid compounds, including imidazo[1,2-<em>a</em>]pyrimidin-2-yl(3-(substituted)quinoxalin-2-yl)methanone and its imidazo[1,2-<em>a</em>]pyridine analogs, have been successfully prepared via palladium-catalyzed reactions. The synthesis involved the reaction of 3-substituted-2-chloroquinoxalines with 2-amino-1-(prop-2-yn-1-yl)pyrimidinium/pyridinium bromide under optimized reaction conditions. These conditions included Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub> (5 mol %), CuI (10 mol%) in the presence of Et<sub>3</sub>N in DMF at 70 °C, resulting in the formation of the desired hybrid compounds. Furthermore, imidazo[1,2-<em>a</em>]pyridine hybrid compounds were synthesized through one-pot multicomponent reactions of 2,3-dicholoroquinoxaline, 2-amino-1-(prop-2-yn-1-yl)pyridinium bromide, primary and secondary amines, under optimized conditions. These processes provided efficient protocols to synthesize novel imidazo[1,2-<em>a</em>]pyrimidine/pyridine based on quinoxaline through palladium-catalyzed reaction with high yields. A one-pot reaction, high reaction yields, energy efficiency, and a straightforward reaction process are significant advantages of this protocol.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134521"},"PeriodicalIF":2.1,"publicationDate":"2025-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143387428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-08DOI: 10.1016/j.tet.2025.134522
Sunwu Song , Siyang Feng , Liangxuan Wang , Begoña Milián-Medina , Reinhold Wannemacher , Johannes Gierschner , Min Sang Kwon
In a recent study, we synthesized novel, color-pure blue emitters, based on a simple ‘pencil and paper’ concept, termed DOBFT and DOBFIT, inspired by our ‘Poly-Heteroaromatic Omni-Delocalization’ (PHOD) concept. The molecules' asymmetric structure, distinct from the DABNA framework, posed significant synthetic challenges, necessitating careful modification of existing strategies and considerable trial and error. While previous publications have primarily focused on the PHOD concept and the properties of DOBFT and DOBFIT, they often overlooked the complexities of their synthesis. In this paper, we provide a detailed account of the synthesis processes and challenges, offering valuable insights for researchers pursuing similar efforts. Additionally, we introduce a new molecule, DOBFITX, with its synthesis meticulously documented, along with a comprehensive, combined spectroscopic and computational analysis of the photophysical properties of these molecules.
{"title":"Synthesis and photophysics of color-pure blue emitters featuring oxaboraphenanthrene as a novel structural motif","authors":"Sunwu Song , Siyang Feng , Liangxuan Wang , Begoña Milián-Medina , Reinhold Wannemacher , Johannes Gierschner , Min Sang Kwon","doi":"10.1016/j.tet.2025.134522","DOIUrl":"10.1016/j.tet.2025.134522","url":null,"abstract":"<div><div>In a recent study, we synthesized novel, color-pure blue emitters, based on a simple ‘pencil and paper’ concept, termed DOBFT and DOBFIT, inspired by our ‘Poly-Heteroaromatic Omni-Delocalization’ (PHOD) concept. The molecules' asymmetric structure, distinct from the DABNA framework, posed significant synthetic challenges, necessitating careful modification of existing strategies and considerable trial and error. While previous publications have primarily focused on the PHOD concept and the properties of DOBFT and DOBFIT, they often overlooked the complexities of their synthesis. In this paper, we provide a detailed account of the synthesis processes and challenges, offering valuable insights for researchers pursuing similar efforts. Additionally, we introduce a new molecule, DOBFITX, with its synthesis meticulously documented, along with a comprehensive, combined spectroscopic and computational analysis of the photophysical properties of these molecules.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134522"},"PeriodicalIF":2.1,"publicationDate":"2025-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143396262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Three zinc porphyrin dendrimer analogs with rigid conjugated backbones were synthesized and connected via a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction to form a trimer with two flexible linkages. Comparison of the 1H NMR and UV–vis absorption spectra of the trimer with those of the corresponding monomers indicated that the trimer adopted an extended conformation in chloroform. The addition of a Y-shaped ligand with three pyridyl terminals to a chloroform solution of the trimer resulted in the formation of a 1:1 complex between the trimer and ligand. A binding constant of K = 2.7 × 106 M−1 was estimated by UV–vis titration. The characteristic up-field shift of the signals for pyridine protons was observed in the 1H NMR spectrum of the 1:1 mixture of the trimer and ligand. Theoretical calculations suggested that coordination of pyridyl terminals to three zinc porphyrin cores led to the trimer adopting a cyclic conformation.
{"title":"Ligand-induced transformation to cyclic conformation of trimers of porphyrin dendrimer analogs","authors":"Takumi Nakao , Yoshimitsu Tachi , Masatoshi Kozaki","doi":"10.1016/j.tet.2025.134523","DOIUrl":"10.1016/j.tet.2025.134523","url":null,"abstract":"<div><div>Three zinc porphyrin dendrimer analogs with rigid conjugated backbones were synthesized and connected via a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction to form a trimer with two flexible linkages. Comparison of the <sup>1</sup>H NMR and UV–vis absorption spectra of the trimer with those of the corresponding monomers indicated that the trimer adopted an extended conformation in chloroform. The addition of a Y-shaped ligand with three pyridyl terminals to a chloroform solution of the trimer resulted in the formation of a 1:1 complex between the trimer and ligand. A binding constant of <em>K</em> = 2.7 × 10<sup>6</sup> M<sup>−1</sup> was estimated by UV–vis titration. The characteristic up-field shift of the signals for pyridine protons was observed in the <sup>1</sup>H NMR spectrum of the 1:1 mixture of the trimer and ligand. Theoretical calculations suggested that coordination of pyridyl terminals to three zinc porphyrin cores led to the trimer adopting a cyclic conformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134523"},"PeriodicalIF":2.1,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143403012","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-05DOI: 10.1016/j.tet.2025.134518
Praveenakumara A. Valmiki , Lohit Naik , M.S. Thippeswamy , C.V. Maridevarmath , Arun K. Shetter , Amnah Mohammed Alsuhaibani , Moamen S. Refat , G.H. Malimath
In this study, a highly fluorescent fluorescein-based derivative (2FLC) was synthesized using a one-pot synthesis method. The structure of the molecule was confirmed through physicochemical analysis, including 1H NMR, FT-IR, and mass spectroscopy. The chemosensor property of 2FLC with different metal ions (Cu 2+, Al3+, Ag +, Hg2+, Mg2+, Fe2+, Co2+, K+, Zn2+, Ni2+, Pb2+, Cd2+ and Mn2+) is investigated through absorption and fluorescence studies in a water medium. Interestingly, it is observed that the 2FLC exhibited a remarkable turn-off fluorescence response upon adding Hg2+ ion as compared to different metal ions. Further, competitive metal ion studies indicate that the receptor 2FLC exhibits exceptional selectivity in detecting Hg2+ ion without being affected by other metal ions. The detection limit of 2FLC for targeted Hg2+ ion was 8.87 μM. The binding stoichiometry between the receptor 2FLC and the Hg2+ metal ion was verified using both Job's plot and the Benasi-Hildbrand methods and found to be 1:1. Theoretical studies and FT-IR spectra confirmed the strong binding and formation of 2FLC-Hg2+ complex. Overall, the results suggest that the newly synthesized water-soluble 2FLC molecule may be used as a chemosensor to detect Hg2+ ion.
{"title":"One pot synthesis of coumarin fused fluorescein derivative for mercury ion detection: An experimental and theoretical approach","authors":"Praveenakumara A. Valmiki , Lohit Naik , M.S. Thippeswamy , C.V. Maridevarmath , Arun K. Shetter , Amnah Mohammed Alsuhaibani , Moamen S. Refat , G.H. Malimath","doi":"10.1016/j.tet.2025.134518","DOIUrl":"10.1016/j.tet.2025.134518","url":null,"abstract":"<div><div>In this study, a highly fluorescent fluorescein-based derivative (2FLC) was synthesized using a one-pot synthesis method. The structure of the molecule was confirmed through physicochemical analysis, including <sup>1</sup>H NMR, FT-IR, and mass spectroscopy. The chemosensor property of 2FLC with different metal ions (Cu <sup>2+</sup>, Al<sup>3+</sup>, Ag <sup>+</sup>, Hg<sup>2+</sup>, Mg<sup>2+</sup>, Fe<sup>2+</sup>, Co<sup>2+</sup>, K<sup>+</sup>, Zn<sup>2+</sup>, Ni<sup>2+</sup>, Pb<sup>2+</sup>, Cd<sup>2+</sup> and Mn<sup>2+</sup>) is investigated through absorption and fluorescence studies in a water medium. Interestingly, it is observed that the 2FLC exhibited a remarkable turn-off fluorescence response upon adding Hg<sup>2+</sup> ion as compared to different metal ions. Further, competitive metal ion studies indicate that the receptor 2FLC exhibits exceptional selectivity in detecting Hg<sup>2+</sup> ion without being affected by other metal ions. The detection limit of 2FLC for targeted Hg<sup>2+</sup> ion was 8.87 μM. The binding stoichiometry between the receptor 2FLC and the Hg<sup>2+</sup> metal ion was verified using both Job's plot and the Benasi-Hildbrand methods and found to be 1:1. Theoretical studies and FT-IR spectra confirmed the strong binding and formation of 2FLC-Hg<sup>2+</sup> complex. Overall, the results suggest that the newly synthesized water-soluble 2FLC molecule may be used as a chemosensor to detect Hg<sup>2+</sup> ion.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134518"},"PeriodicalIF":2.1,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143387429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Click chemistry, celebrated for its efficiency and selectivity, has emerged as a powerful tool for the rapid synthesis of tetrazines. This study introduces a novel approach to accessing tetrazines from symmetrical azines and sodium azide, facilitating the streamlined construction of these versatile compounds. Renowned for their exceptional stability and reactivity, tetrazines are highly coveted in diverse fields including materials science, medicinal chemistry, and imaging. The newly synthesized tetrazine derivatives were rigorously characterized using a suite of spectroscopic techniques, including IR, 1H and 13C NMR, 2D NMR, and mass spectrometry. To assess their reactivity and stability, the energy gap (ΔE) was computed using density functional theory. Furthermore, in silico molecular docking studies were performed against the muscular dystrophy protein 2VD5 to explore its potential biological activity. This innovative synthetic strategy provides a robust platform for the expeditious development of a diverse array of tetrazine-based compounds with promising applications across various scientific domains.
{"title":"Click synthesis via 1,3-dipolar addition- A versatile route to tetrazine derivatives and In silico corroboration as anti-muscular dystrophy agent","authors":"Satheeshkumar Nagaraj, Karpagam Ezhilarasan, Rajalakshmi Ramarajan","doi":"10.1016/j.tet.2025.134520","DOIUrl":"10.1016/j.tet.2025.134520","url":null,"abstract":"<div><div>Click chemistry, celebrated for its efficiency and selectivity, has emerged as a powerful tool for the rapid synthesis of tetrazines. This study introduces a novel approach to accessing tetrazines from symmetrical azines and sodium azide, facilitating the streamlined construction of these versatile compounds. Renowned for their exceptional stability and reactivity, tetrazines are highly coveted in diverse fields including materials science, medicinal chemistry, and imaging. The newly synthesized tetrazine derivatives were rigorously characterized using a suite of spectroscopic techniques, including IR, <sup>1</sup>H and <sup>13</sup>C NMR, 2D NMR, and mass spectrometry. To assess their reactivity and stability, the energy gap (ΔE) was computed using density functional theory. Furthermore, in silico molecular docking studies were performed against the muscular dystrophy protein 2VD5 to explore its potential biological activity. This innovative synthetic strategy provides a robust platform for the expeditious development of a diverse array of tetrazine-based compounds with promising applications across various scientific domains.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134520"},"PeriodicalIF":2.1,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143349082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01DOI: 10.1016/j.tet.2024.134428
Azim Ziyaei Halimehjani, Nima Sadeghzadeh, Sina Moghaddam
Azoarenes are efficient intermediates in synthetic organic chemistry. In this review, the application of azoarenes for the synthesis of nitrogen-containing heterocyles including pyrroles, benzotriazoles, triazolidines, indoles, indazoles, oxindoles, quinolines and its reduced derivatives, phenazines, hydropyridazinones, cinnolines, benzimidazoles and other useful N-containing heterocycles are reviewed and discussed. For this purpose, the reaction of azoarenes with various organic small molecules such as alkenes, alkynes, azides, NO2 gas, nitroso, amino acids, azomethine ylides, canbonyl compounds, diazoesteres, sulfoxonium ylides, tosyl hydrazines, allyl halides, and many other reagents were investigated under metal/transition-metal catalysts, photocatalysts, or electrochemical conditions to afford the target heterocycles with at least one nitrogen atom. In this review, around 70 papers are summarized and discussed during the years 2000–2024.
偶氮烯类是合成有机化学中的高效中间体。本综述回顾并讨论了偶氮烯在合成含氮杂环方面的应用，包括吡咯、苯并三唑、三唑烷、吲哚、吲哚、氧吲哚、喹啉及其还原衍生物、吩嗪、哒嗪酮、噌啉、苯并咪唑和其他有用的含 N 杂环。为此，在金属/过渡金属催化剂、光催化剂或电化学条件下，研究了偶氮烯与各种有机小分子（如烯烃、炔烃、叠氮化物、NO2 气体、亚硝基、氨基酸、偶氮甲基酰化物、羰基化合物、重氮酯、亚砜酰化物、对甲苯基肼、烯丙基卤化物和许多其他试剂）的反应，从而得到至少含有一个氮原子的目标杂环。本综述对 2000-2024 年间约 70 篇论文进行了总结和讨论。
{"title":"The application of azoarenes in the synthesis of nitrogen-containing heterocycles","authors":"Azim Ziyaei Halimehjani, Nima Sadeghzadeh, Sina Moghaddam","doi":"10.1016/j.tet.2024.134428","DOIUrl":"10.1016/j.tet.2024.134428","url":null,"abstract":"<div><div>Azoarenes are efficient intermediates in synthetic organic chemistry. In this review, the application of azoarenes for the synthesis of nitrogen-containing heterocyles including pyrroles, benzotriazoles, triazolidines, indoles, indazoles, oxindoles, quinolines and its reduced derivatives, phenazines, hydropyridazinones, cinnolines, benzimidazoles and other useful <em>N</em>-containing heterocycles are reviewed and discussed. For this purpose, the reaction of azoarenes with various organic small molecules such as alkenes, alkynes, azides, NO<sub>2</sub> gas, nitroso, amino acids, azomethine ylides, canbonyl compounds, diazoesteres, sulfoxonium ylides, tosyl hydrazines, allyl halides, and many other reagents were investigated under metal/transition-metal catalysts, photocatalysts, or electrochemical conditions to afford the target heterocycles with at least one nitrogen atom. In this review, around 70 papers are summarized and discussed during the years 2000–2024.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134428"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182074","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01DOI: 10.1016/j.tet.2024.134423
Binbin Zhou , Huacan Xv , Ke Zhang , Xv Han , Shuhao Liu , Jiayu He , Jinwei Sun , Yuling Li , Yun Liu
A practical synthesis of indolizine-3-carboxylates has been developed via copper-promoted reaction of alkenoic acids with bromoesters and pyridines using air as the terminal oxidant. In this reaction, carboxyl group acts as a traceless substituent to activate carbon-carbon double bond. By this protocol, we have successfully obtained indolizine-3-carboxylates with aryl or alkyl group at 1-position or 2-position of indolizine motif. This protocol features advantages of simple reaction conditions as well as broad substituents kinds.
{"title":"An efficient approach to indolizine-3-carboxylates via Cu(I)-promoted decarboxylative cycloaddition of alkenoic acids","authors":"Binbin Zhou , Huacan Xv , Ke Zhang , Xv Han , Shuhao Liu , Jiayu He , Jinwei Sun , Yuling Li , Yun Liu","doi":"10.1016/j.tet.2024.134423","DOIUrl":"10.1016/j.tet.2024.134423","url":null,"abstract":"<div><div>A practical synthesis of indolizine-3-carboxylates has been developed <em>via</em> copper-promoted reaction of alkenoic acids with bromoesters and pyridines using air as the terminal oxidant. In this reaction, carboxyl group acts as a traceless substituent to activate carbon-carbon double bond. By this protocol, we have successfully obtained indolizine-3-carboxylates with aryl or alkyl group at 1-position or 2-position of indolizine motif. This protocol features advantages of simple reaction conditions as well as broad substituents kinds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134423"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181109","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01DOI: 10.1016/j.tet.2024.134425
Jiaxi Xu
Phosphetane derivatives are a class of four-membered saturated phosphorus-containing heterocycles and have been widely applied as phosphorus-containing chiral ligands in asymmetric catalytic organic reactions. Synthetic methods for phosphetane derivatives are divided mainly into double nucleophilic substitutions, electrophilic addition of phospheniums to olefins and subsequent cyclization, electrophilic ring expansions of cyclopropanes and phosphiranes, cycloaddition and electrocyclic reaction, etc. The scope, limitation, regio- and stereoselectivities, and proposed reaction mechanisms are also discussed for some methods. Further development for preparation of phosphetane derivatives and their application are also prospected.
{"title":"Synthesis of phosphetane derivatives","authors":"Jiaxi Xu","doi":"10.1016/j.tet.2024.134425","DOIUrl":"10.1016/j.tet.2024.134425","url":null,"abstract":"<div><div>Phosphetane derivatives are a class of four-membered saturated phosphorus-containing heterocycles and have been widely applied as phosphorus-containing chiral ligands in asymmetric catalytic organic reactions. Synthetic methods for phosphetane derivatives are divided mainly into double nucleophilic substitutions, electrophilic addition of phospheniums to olefins and subsequent cyclization, electrophilic ring expansions of cyclopropanes and phosphiranes, cycloaddition and electrocyclic reaction, etc. The scope, limitation, regio- and stereoselectivities, and proposed reaction mechanisms are also discussed for some methods. Further development for preparation of phosphetane derivatives and their application are also prospected.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134425"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182101","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01DOI: 10.1016/j.tet.2024.134414
Dang Viet Anh , Tran Hong Quang , Ninh Thi Ngoc , Tran Thi Hong Hanh , Nguyen Xuan Cuong , Nguyen Thi Thanh Ngan , Nguyen Ngoc Tung , Nguyen Hoai Nam , Chau Van Minh
Chemical investigation of the mangrove-derived fungus Aspergillus sp. DVXT-221 led to isolation of three undescribed ergot alkaloids, fumigaclavines K−M (1, 2, and 4), and seven known compounds, fumigaclavines I (3), C (5), and E (6), monomethylsulochrin (7), 8′-O-methylasterric acid (8), 2,3′-dimethylosoate (9), and chaetominine (10). Their structures were identified by comprehensive analyses of the spectroscopic methods, including NMR and HRESI mass spectra. The absolute configurations of 1, 2, and 4 were clarified by time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) spectroscopic analyses. Compound 2 contained the first example of N-methyl oxide among the previously reported ergot alkaloids. Compounds 1 and 3 showed weak cytotoxicity on both HepG2 and MCF7 cell lines, with IC50 values ranging from 61.1 ± 3.1 to 77.2 ± 1.5 μM. Compounds 1 and 9 exhibited stronger inhibitory effect on nitric oxide (NO) production in LPS-stimulated RAW264.7 cells, with IC50 values of 5.3 ± 0.2 and 8.7 ± 0.4 μM, respectively, whereas weaker NO inhibitory effects were observed for 2–4, 8, and 10, with IC50 values ranging from 20.5 ± 0.8 to 36.1 ± 2.3 μM. Both 1 and 9 were suggested to inhibit NO overproduction via down-regulating the action of iNOS protein by molecular docking simulations.
{"title":"Fumigaclavines K−M, undescribed ergot alkaloids from the mangrove-derived fungus Aspergillus sp. DVXT-221 with cytotoxic and NO inhibitory activities","authors":"Dang Viet Anh , Tran Hong Quang , Ninh Thi Ngoc , Tran Thi Hong Hanh , Nguyen Xuan Cuong , Nguyen Thi Thanh Ngan , Nguyen Ngoc Tung , Nguyen Hoai Nam , Chau Van Minh","doi":"10.1016/j.tet.2024.134414","DOIUrl":"10.1016/j.tet.2024.134414","url":null,"abstract":"<div><div>Chemical investigation of the mangrove-derived fungus <em>Aspergillus</em> sp. DVXT-221 led to isolation of three undescribed ergot alkaloids, fumigaclavines K−M (<strong>1</strong>, <strong>2</strong>, and <strong>4</strong>), and seven known compounds, fumigaclavines I (<strong>3</strong>), C (<strong>5</strong>), and E (<strong>6</strong>), monomethylsulochrin (<strong>7</strong>), 8′-O-methylasterric acid (<strong>8</strong>), 2,3′-dimethylosoate (<strong>9</strong>), and chaetominine (<strong>10</strong>). Their structures were identified by comprehensive analyses of the spectroscopic methods, including NMR and HRESI mass spectra. The absolute configurations of <strong>1</strong>, <strong>2</strong>, and <strong>4</strong> were clarified by time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) spectroscopic analyses. Compound <strong>2</strong> contained the first example of N-methyl oxide among the previously reported ergot alkaloids. Compounds <strong>1</strong> and <strong>3</strong> showed weak cytotoxicity on both HepG2 and MCF7 cell lines, with IC<sub>50</sub> values ranging from 61.1 ± 3.1 to 77.2 ± 1.5 μM. Compounds <strong>1</strong> and <strong>9</strong> exhibited stronger inhibitory effect on nitric oxide (NO) production in LPS-stimulated RAW264.7 cells, with IC<sub>50</sub> values of 5.3 ± 0.2 and 8.7 ± 0.4 μM, respectively, whereas weaker NO inhibitory effects were observed for <strong>2–4</strong>, <strong>8</strong>, and <strong>10</strong>, with IC<sub>50</sub> values ranging from 20.5 ± 0.8 to 36.1 ± 2.3 μM. Both <strong>1</strong> and <strong>9</strong> were suggested to inhibit NO overproduction via down-regulating the action of iNOS protein by molecular docking simulations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134414"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181146","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01DOI: 10.1016/j.tet.2024.134422
Jiahong Chen, Mengke Wang, Weichun Huang, You Zi
A mild and convenient method for synthesizing thioesters has been developed, from sulfenylchlorides and carboxylic acids via a phosphine mediated umpolung process. This approach efficiently produces a broad spectrum of thioesters from readily available carboxylic acids, including primary, secondary, and tertiary types, as well as bioactive molecules. The successful gram-scale reactions also validate its scalability and practical application.
{"title":"An efficient method for thioesterification of carboxylic acid with sulfenylchloride","authors":"Jiahong Chen, Mengke Wang, Weichun Huang, You Zi","doi":"10.1016/j.tet.2024.134422","DOIUrl":"10.1016/j.tet.2024.134422","url":null,"abstract":"<div><div>A mild and convenient method for synthesizing thioesters has been developed, from sulfenylchlorides and carboxylic acids via a phosphine mediated umpolung process. This approach efficiently produces a broad spectrum of thioesters from readily available carboxylic acids, including primary, secondary, and tertiary types, as well as bioactive molecules. The successful gram-scale reactions also validate its scalability and practical application.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134422"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181116","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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