Beilstein Journal of Organic Chemistry最新文献

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Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-02-11 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.23
Rita Toshe, Syeda J Khalid, Blondelle Matio Kemkuignou, Esteban Charria-Girón, Paul Eckhardt, Birthe Sandargo, Kunlapat Nuchthien, J Jennifer Luangsa-Ard, Till Opatz, Hedda Schrey, Sherif S Ebada, Marc Stadler
{"title":"Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus <i>Samsoniella aurantia</i>.","authors":"Rita Toshe, Syeda J Khalid, Blondelle Matio Kemkuignou, Esteban Charria-Girón, Paul Eckhardt, Birthe Sandargo, Kunlapat Nuchthien, J Jennifer Luangsa-Ard, Till Opatz, Hedda Schrey, Sherif S Ebada, Marc Stadler","doi":"10.3762/bjoc.21.23","DOIUrl":"10.3762/bjoc.21.23","url":null,"abstract":"<p><p>During the course of our studies on the secondary metabolism of rare, hitherto untapped Thai insect-associated fungi, the ethyl acetate (EtOAc) extract derived from solid-state cultivation of <i>Samsoniella aurantia</i> on rice afforded one previously undescribed tetramic acid derivative, farinosone D (<b>1</b>), along with the known 2-pyridones, farinosones A (<b>2</b>) and B (<b>3</b>), and the known cyclodepsipeptides beauvericins A-C (<b>4</b>-<b>6</b>). All isolated compounds were assessed for their antimicrobial and cytotoxic activities while farinosones D (<b>1</b>) and A (<b>2</b>) were selected for biofilm inhibitory activity assay. Farinosone B (<b>3</b>) and beauvericins A-C (<b>4</b>-<b>6</b>) showed significant cytotoxic activities with IC<sub>50</sub> values in the low micromolar to nanomolar range against several mammalian cell lines. On the other hand, farinosone A (<b>2</b>), which lacked potent cytotoxic effects, revealed potent antibiofilm activity, inhibiting approximately 70% of <i>Staphylococcus aureus</i> biofilms at concentrations as low as 3.9 µg/mL.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"327-339"},"PeriodicalIF":2.2,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11833177/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447838","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Red light excitation: illuminating photocatalysis in a new spectrum.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-02-07 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.22
Lucas Fortier, Corentin Lefebvre, Norbert Hoffmann
{"title":"Red light excitation: illuminating photocatalysis in a new spectrum.","authors":"Lucas Fortier, Corentin Lefebvre, Norbert Hoffmann","doi":"10.3762/bjoc.21.22","DOIUrl":"10.3762/bjoc.21.22","url":null,"abstract":"<p><p>Red-light-activated photocatalysis has become a powerful approach for achieving sustainable chemical transformations, combining high efficiency with energy-saving, mild conditions. By harnessing the deeper penetration and selectivity of red and near-infrared light, this method minimizes the side reactions typical of higher-energy sources, making it particularly suited for large-scale applications. Recent advances highlight the unique advantages of both metal-based and metal-free catalysts under red-light irradiation, broadening the range of possible reactions, from selective oxidations to complex polymerizations. In biological contexts, red-light photocatalysis enables innovative applications in phototherapy and controlled drug release, exploiting its tissue penetration and low cytotoxicity. Together, these developments underscore the versatility and impact of red-light photocatalysis, positioning it as a cornerstone of green organic chemistry with significant potential in synthetic and biomedical fields.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"296-326"},"PeriodicalIF":2.2,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809576/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389909","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-02-05 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.20
Abel Cárdenas, Zexin Jin, Yong Ni, Jishan Wu, Yan Xia, Francisco Javier Ramírez, Juan Casado
{"title":"Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity.","authors":"Abel Cárdenas, Zexin Jin, Yong Ni, Jishan Wu, Yan Xia, Francisco Javier Ramírez, Juan Casado","doi":"10.3762/bjoc.21.20","DOIUrl":"10.3762/bjoc.21.20","url":null,"abstract":"<p><p>Oxidized states of polycyclic aromatic hydrocarbons are of importance as they represent charged conductive species in organic semiconductor substrates. In this work, we investigated the properties of radical cations and dications of linear and angular [3]naphthylenes, consisting of fused aromatic naphthalenoid and antiaromatic cyclobutadienoid moieties and containing different degrees of paratropicity. Electronic absorption and vibrational Raman spectroscopies were used to describe the more relevant bonding changes. Stretching force constants were evaluated to monitor the aromatic-antiaromatic alternation pattern upon oxidation. They showed us that the dication of linear [3]naphthylene became an overall global π-electron delocalized molecule. This result was supported by nucleus independent chemical shift (NICS) calculations and anisotropy of the current induced density (ACID) plots, as they evidenced the presence of a perimetral diatropic global ring current upon oxidation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"277-285"},"PeriodicalIF":2.2,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809581/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389905","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-02-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.18
Dmitry E Shybanov, Maxim E Kukushkin, Eugene V Babaev, Nikolai V Zyk, Elena K Beloglazkina
{"title":"Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions.","authors":"Dmitry E Shybanov, Maxim E Kukushkin, Eugene V Babaev, Nikolai V Zyk, Elena K Beloglazkina","doi":"10.3762/bjoc.21.18","DOIUrl":"10.3762/bjoc.21.18","url":null,"abstract":"<p><p>A diffusion mixing technique with a volatile reagent was successfully used to generate crotonic condensation adducts of active methylene compounds and formaldehyde at room temperature in the absence of strong acids and bases. The formed adducts were highly reactive intermediates capable of reacting with dienes in a three-component reaction, leading to the formation of Diels-Alder main reaction products.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"262-269"},"PeriodicalIF":2.2,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809574/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389932","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-02-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.19
Islam S Marae, Jingyun Tan, Rengo Yoshioka, Zakaria Ziadi, Eugene Khaskin, Serhii Vasylevskyi, Ryota Kabe, Xiushang Xu, Akimitsu Narita
{"title":"Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[<i>rst</i>]pentaphene.","authors":"Islam S Marae, Jingyun Tan, Rengo Yoshioka, Zakaria Ziadi, Eugene Khaskin, Serhii Vasylevskyi, Ryota Kabe, Xiushang Xu, Akimitsu Narita","doi":"10.3762/bjoc.21.19","DOIUrl":"10.3762/bjoc.21.19","url":null,"abstract":"<p><p>A benzo[<i>rst</i>]pentaphene (BPP) substituted by an isopropoxy group (BPP-OiPr) was synthesized in a facile manner. Its photophysical properties were investigated by UV-vis absorption and fluorescence spectroscopy in compassion to pristine BPP and its oxidation product, benzo[<i>rst</i>]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP (13%). BPP-dione, when compared to the parent BPP, also displayed improved absorption and emission from the first excited singlet (S<sub>1</sub>) state with a PLQY of 62% and an intramolecular charge-transfer character. The rod-like nano- to microcrystals as well as longer wires of these BPPs were also revealed by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"270-276"},"PeriodicalIF":2.2,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809583/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389915","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-02-03 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.17
Zhenlei Zhang, Ying Wang, Xingxing Pan, Manqi Zhang, Wei Zhao, Meng Li, Hao Zhang
{"title":"Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI.","authors":"Zhenlei Zhang, Ying Wang, Xingxing Pan, Manqi Zhang, Wei Zhao, Meng Li, Hao Zhang","doi":"10.3762/bjoc.21.17","DOIUrl":"10.3762/bjoc.21.17","url":null,"abstract":"<p><p>A new synthetic method for disulfides and 3-sulfenylchromones is reported. This innovative approach is based on the tetrabutylammonium iodide (TBAI)/H<sub>2</sub>SO<sub>4</sub> reduction system using sodium sulfinate as key component, thus eliminating the need for thiols and redox reagents commonly used in traditional methods. Various disulfides and 3-sulfenylchromones were obtained in moderate to excellent yields through this methodology. Mechanistic studies indicate that thiosulfonates play an important role in the reaction process.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"253-261"},"PeriodicalIF":2.2,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11809575/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389922","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-31 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.16
Misato Suganuma, Daichi Kitagawa, Shota Hamatani, Seiya Kobatake
{"title":"Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory.","authors":"Misato Suganuma, Daichi Kitagawa, Shota Hamatani, Seiya Kobatake","doi":"10.3762/bjoc.21.16","DOIUrl":"10.3762/bjoc.21.16","url":null,"abstract":"<p><p>Aza-diarylethene has been developed as a new family of photochromic compounds. This study explores the photochromic properties and thermal back reactivities of various aza-diarylethene regioisomers (<b>N1</b>-<b>N4</b> and <b>I1</b>-<b>I4</b>) in <i>n</i>-hexane. These molecules exhibit fast thermally reversible photochromic reactions driven by 6π aza-electrocyclization. Kinetic analysis of the thermal back reaction revealed activation parameters, highlighting how the substitution position of the aryl group affects the thermal stability. Additionally, density functional theory calculations identified M06 and MPW1PW91 as the most accurate functionals for predicting the thermal back reactivity, closely matching the experimental data. These findings offer valuable insights for the design of advanced photochromic materials with tailored thermal and photophysical characteristics.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"242-252"},"PeriodicalIF":2.2,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11789678/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121747","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-30 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.15
Yujun Pang, Jinglan Yan, Nawaf Al-Maharik, Qian Zhang, Zeguo Fang, Dong Li
{"title":"Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles.","authors":"Yujun Pang, Jinglan Yan, Nawaf Al-Maharik, Qian Zhang, Zeguo Fang, Dong Li","doi":"10.3762/bjoc.21.15","DOIUrl":"10.3762/bjoc.21.15","url":null,"abstract":"<p><p>An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive CF<sub>2</sub>HCO<sub>2</sub>H or PhCF<sub>2</sub>COOH, along with benzimidazoles bearing unactivated alkenes and PhI(OAc)<sub>2</sub> as substrates, and proceeded without the need of any base, metal catalyst, photocatalyst or additive. In total, 24 examples were examined, and all of them successfully underwent cyclization reaction to produce the target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"234-241"},"PeriodicalIF":2.2,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11789676/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121854","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-28 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.14
Asahi Kanno, Ryo Tanifuji, Satoshi Yoshida, Sota Sato, Saori Maki-Yonekura, Kiyofumi Takaba, Jungmin Kang, Kensuke Tono, Koji Yonekura, Hiroki Oguri
{"title":"Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-<i>endo</i> cyclization.","authors":"Asahi Kanno, Ryo Tanifuji, Satoshi Yoshida, Sota Sato, Saori Maki-Yonekura, Kiyofumi Takaba, Jungmin Kang, Kensuke Tono, Koji Yonekura, Hiroki Oguri","doi":"10.3762/bjoc.21.14","DOIUrl":"10.3762/bjoc.21.14","url":null,"abstract":"<p><p>The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-<i>endo</i> cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-<i>endo</i> hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected involvement of a fluorescent intermediate in the cascade synthetic process.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"226-233"},"PeriodicalIF":2.2,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11789684/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121825","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide.
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-01-24 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.13
Marios Zingiridis, Danae Papachristodoulou, Despoina Menegaki, Konstantinos G Froudas, Constantinos G Neochoritis
{"title":"Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide.","authors":"Marios Zingiridis, Danae Papachristodoulou, Despoina Menegaki, Konstantinos G Froudas, Constantinos G Neochoritis","doi":"10.3762/bjoc.21.13","DOIUrl":"10.3762/bjoc.21.13","url":null,"abstract":"<p><p>C1 chemistry has a central role in the efficient utilization of single-carbon molecules, contributing significantly to sustainability, innovation and economic growth across various sectors. In this study, we present an efficient and rapid method for synthesizing a variety of heteroannulated pyrimidones using cyanoacetamide-based multicomponent reaction (MCR) chemistry. By utilizing specific MCR-based scaffolds as precursors and employing the abundant and inexpensive formamide as a C1 feedstock under neat conditions, we were able to efficiently access substituted thieno-, quinolino- and indolopyrimidones without the need of column chromatography. Further, a single-crystal X-ray structure was obtained, revealing certain geometrical features.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"217-225"},"PeriodicalIF":2.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11773184/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143057879","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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