Organic & Biomolecular Chemistry最新文献_第3页

Discovery of novel cinnamamide derivatives as potent antifungal agents: design, synthesis, and biological evaluation. 发现新的肉桂酰胺衍生物作为有效的抗真菌剂：设计，合成和生物学评价。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01168c

Yukang Liu, Xinyi Lu, Zhengyu Liu, Xiuyun Sheng, Jinkui Jia, Ting Zhao, Min Zhang, Liuqing Yang, Changsheng Yao

{"title":"Discovery of novel cinnamamide derivatives as potent antifungal agents: design, synthesis, and biological evaluation.","authors":"Yukang Liu, Xinyi Lu, Zhengyu Liu, Xiuyun Sheng, Jinkui Jia, Ting Zhao, Min Zhang, Liuqing Yang, Changsheng Yao","doi":"10.1039/d6ob01168c","DOIUrl":"https://doi.org/10.1039/d6ob01168c","url":null,"abstract":"This work was motivated by the severe impact of plant fungal diseases on agriculture and the numerous issues associated with traditional chemical fungicides. This study employed a molecular hybridization strategy to synthesize 25 novel cinnamamide compounds, 7a-7t and 8a-8e, and evaluated their antifungal activities against seven plant pathogenic fungi at a concentration of 50 mg L-1. These compounds exhibit inhibition rates ranging from 10.9% to 92.4%, with compound 8a showing high broad-spectrum antifungal efficacies. Compound 8e is highly selective and potent against Rhizoctonia cerealis, with an EC50 value of 13.80 mg L-1, making it 7-fold more potent than the control fungicide boscalid. Molecular docking studies suggest that compound 8a efficiently binds to succinate dehydrogenase through hydrogen bonds and hydrophobic interactions, with a binding energy of -7.7 kcal mol-1, slightly lower than that of boscalid (-7.4 kcal mol-1). This study provides evidence of cinnamamides being fungicidal.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316161","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}

引用次数: 0

An anthracene-based self-assembled macrocycle for recognition of fullerenes. 一种基于蒽基的自组装大环，用于识别富勒烯。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01466f

Fei Zeng, Lin-Li Tang, Jin-Jie Xie, Meng-Jie Tang, Man-Hua Ding

引用次数: 0

Eosin Y-catalyzed cross-dehydrogenative coupling under visible light: metal-free synthetic approaches. 可见光下伊红y催化的交叉脱氢偶联：无金属合成方法。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01377e

Priyanshu Prajapati, Satish Kumar Singh

{"title":"Eosin Y-catalyzed cross-dehydrogenative coupling under visible light: metal-free synthetic approaches.","authors":"Priyanshu Prajapati, Satish Kumar Singh","doi":"10.1039/d6ob01377e","DOIUrl":"https://doi.org/10.1039/d6ob01377e","url":null,"abstract":"Visible-light-driven photocatalysis has emerged as a transformative tool in organic synthesis, enabling diverse bond-forming processes under mild, sustainable conditions. Since 2011, among the range of organic photocatalysts, eosin Y (EY), a low-cost, metal-free organic dye, has gained significant prominence due to its strong visible-light absorption, suitable redox properties, and environmental benignity. Cross-coupling is one of the essential reactions which can enable desired C-C/C-heteroatom (X) (X = N, O, S, P) bond formation. Further cross dehydrogenative coupling (CDC) reactions are known for their unique selectivity as they form desired C-C/C-X bonds directly from C-H bonds without pre-functionalization of the substrates. EY has gained increasing significance in recent CDC reactions owing to its strong visible-light absorption and efficient SET capability, enabling mild oxidative C-H functionalization through metal-free pathways while offering environmentally benign alternatives to transition-metal photocatalysts and improved cross efficiency. Although reviews have broadly covered photoredox catalysis, EY chemistry and CDC, a focused assessment of eosin Y-mediated visible-light-driven CDC reactions remains limited. This review delineates the growing role of EY as a sustainable visible-light photocatalyst in CDC reactions, enabling efficient C-C/C-X bond formation under mild and metal-free conditions with emphasis on substrate scope, reaction conditions, mechanistic pathways, and metal-free versus metal-assisted approaches. Through a critical assessment of reported advances, current limitations, and unresolved challenges, this review highlights future opportunities to develop more selective, efficient, and sustainable cross-dehydrogenative coupling (CDC) methodologies.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316162","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}

引用次数: 0

Novel Borsche-Drechsel type cyclisation of 3-(2-cyclohexylidenehydrazinyl)quinoxalin-2(1H)-ones to construct tetrahydrobenzo[4,5]imidazo[1,2-a]quinoxalin-6(5H)-ones. 新型Borsche-Drechsel型环化3-（2-环己基肼基）喹啉-2(1H)- 1合成四氢苯并[4,5]咪唑[1,2-a]喹啉-6(5H)- 1。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-30 DOI: 10.1039/d6ob01350c

Vakhid A Mamedov, Liliya V Mustakimova, Victor V Syakaev, Il'dar Kh Rizvanov, Olga B Babaeva, Aidar T Gubaidullin, Oleg G Sinyashin

{"title":"Novel Borsche-Drechsel type cyclisation of 3-(2-cyclohexylidenehydrazinyl)quinoxalin-2(1H)-ones to construct tetrahydrobenzo[4,5]imidazo[1,2-a]quinoxalin-6(5H)-ones.","authors":"Vakhid A Mamedov, Liliya V Mustakimova, Victor V Syakaev, Il'dar Kh Rizvanov, Olga B Babaeva, Aidar T Gubaidullin, Oleg G Sinyashin","doi":"10.1039/d6ob01350c","DOIUrl":"https://doi.org/10.1039/d6ob01350c","url":null,"abstract":"Reported herein is a novel cascade Borsche-Drechsel type cyclisation of 3-(2-cyclohexylidenehydrazinyl)quinoxalin-2(1H)-ones, enabling the efficient construction of tetrahydrobenzo-fused imidazo[1,2-a]quinoxalin-6(5H)-one derivatives in good yields. Moreover, this strategy can be extended to other 3-(2-cycloalkylidenehydrazinyl)quinoxalin-2(1H)-one derivatives, providing access to cyclohepteno-, (Z)-cyclododeceno- and 1,2,3,4-tetrahydronaphthaleno-annulated imidazo[1,2-a]quinoxalin-6(5H)-ones in moderate to excellent yields (66-85%). The use of inexpensive and readily available starting materials, broad substrate scope, mild and eco-friendly reaction conditions, and the versatile synthetic utility of the resulting tetrahydrobenzo[4,5]imidazo[1,2-a]quinoxalin-6(5H)-ones render this protocol an attractive and practical synthetic methodology. It was found that tetrahydrobenzo[4,5]imidazo[1,2-a]quinoxalin-6(5H)-ones under standard oxidation conditions in the presence of DDQ unexpectedly undergo alkylation at the nitrogen atoms of the imidazole ring with the participation of xylene, which was used as a solvent. We expect that this first example of aza-Borsche-Drechsel cyclization and the new unconventional alkylation reaction described in this work will not only provide environmentally friendly methods for producing a wide range of tetrahydrobenzo[4,5]imidazo[1,2-a]quinoxalin-6(5H)-one derivatives but will also facilitate the further development of these types of reactions on other heterocyclic platforms.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149293320","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}

引用次数: 0

Organophotocatalytic hydrosilylation of unactivated α,β-unsaturated amides via aminyl radical-activated silylboronates. 通过氨基自由基活化的硅硼酸盐，有机光催化未活化的α，β-不饱和酰胺的硅氢化反应。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-30 DOI: 10.1039/d6ob01576j

Ronghui Huang, Jingtao Tang, Shilei Yan, Yang Zhang, Fen-Er Chen

引用次数: 0

Robust continuous-flow oxidation of aryl-alkyl sulfides to sulfoxides and sulfones over titanium silicalite-1 using diluted hydrogen peroxide. 用稀释的过氧化氢在硅酸钛-1上连续氧化芳基烷基硫化物生成亚砜和砜。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-30 DOI: 10.1039/d6ob01341d

Yoshihiro Kon, Haruna Hata, Shun-Ya Onozawa, Toshiyuki Yokoi, Masaru Yoshida, Shū Kobayashi

{"title":"Robust continuous-flow oxidation of aryl-alkyl sulfides to sulfoxides and sulfones over titanium silicalite-1 using diluted hydrogen peroxide.","authors":"Yoshihiro Kon, Haruna Hata, Shun-Ya Onozawa, Toshiyuki Yokoi, Masaru Yoshida, Shū Kobayashi","doi":"10.1039/d6ob01341d","DOIUrl":"https://doi.org/10.1039/d6ob01341d","url":null,"abstract":"A continuous-flow oxidation of sulfides was developed using a titanium silicalite-1 (TS-1) catalyst packed in a silica gel column and a single-phase MeCN solution containing diluted aqueous hydrogen peroxide (H2O2 aq.). Methyl phenyl sulfide afforded methyl phenyl sulfoxide in 91% yield at a residence time of 6.5 min (flow rate: 0.20 mL min-1), whereas increasing the H2O2 loading and reaction temperature afforded methyl phenyl sulfone in 99% yield at the same residence time and flow rate. The method was extended to a range of thioanisoles to afford the corresponding sulfoxides and sulfones, important motifs in pesticides and pharmaceutical intermediates. Notably, high yields were achieved with only 5-10% H2O2 aq., avoiding the use of more concentrated H2O2 aq. (>10%), which can accelerate oxidation but presents explosion hazards. The practicality of the system was further demonstrated by the long-term continuous oxidation of methyl phenyl sulfide to methyl phenyl sulfone, which maintained a yield of over 90% at a residence time of 13 min and a flow rate of 0.10 mL min-1 using a 1.3 mL column reactor for 170 h, producing 15 g of product.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149293295","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}

引用次数: 0

1-(2-Aminophenyl)-1H-pyrrole: a versatile building block for the synthesis of pyrrolo[1,2-a]quinoxaline frameworks. 1-（2-氨基苯基）- 1h -吡咯：合成吡咯[1,2-a]喹啉框架的通用构建块。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-29 DOI: 10.1039/d6ob01326k

Megha Kumari, Ashutosh Dey, Vikash Kumar, Rohit Kumar Maurya, Mahender Khatravath

{"title":"1-(2-Aminophenyl)-1H-pyrrole: a versatile building block for the synthesis of pyrrolo[1,2-a]quinoxaline frameworks.","authors":"Megha Kumari, Ashutosh Dey, Vikash Kumar, Rohit Kumar Maurya, Mahender Khatravath","doi":"10.1039/d6ob01326k","DOIUrl":"https://doi.org/10.1039/d6ob01326k","url":null,"abstract":"Pyrrolo[1,2-a]quinoxalines represent an important class of fused nitrogen-containing heterocycles that have attracted considerable attention because of their diverse biological activities and potential applications in functional materials. Among the various precursors employed for their synthesis, 1-(2-aminophenyl)-1H-pyrrole has emerged as a versatile and readily functionalizable precursor because of its unique ortho-amino-pyrrole arrangement. This review provides a comprehensive overview of recent advances in the synthesis of pyrrolo[1,2-a]quinoxaline derivatives using 1-(2-aminophenyl)-1H-pyrrole, with particular emphasis on developments reported during 2020-2026. The synthetic approaches are systematically classified according to their reaction design and cyclization modes, including Pictet-Spengler-type annulations, decarboxylative oxidative annulations, reductive cyclizations, radical-mediated transformations, transition-metal-catalyzed annulations, one-carbon synthon incorporation, multicomponent reactions, and metal-free oxidative processes. The review further discusses the advantages, synthetic applicability, and limitations of the reported methodologies, while identifying key challenges associated with catalyst dependence, harsh reaction conditions, limited substrate scope, and sustainability. Particular emphasis is placed on mechanistic insights, catalyst-controlled reactivity, substrate scope, and the synthetic utility of these methodologies for the rapid and efficient construction of molecular complexity.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149293274","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}

引用次数: 0

Bioisosteric sulfoxonium ylides as building blocks for accessing thiazole derivatives using flow chemistry. 生物等构亚砜酰化物作为流动化学获得噻唑衍生物的基础。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-29 DOI: 10.1039/d6ob01449f

Rouven Fritzius, Paul Wiebe, Jan H Griwatz, Armin Bauer, Anika Tarasewicz, Thomas C Maier, Christian Kramer, Lucas Vidal, Christophe Aïssa, María Méndez, Hermann A Wegner

{"title":"Bioisosteric sulfoxonium ylides as building blocks for accessing thiazole derivatives using flow chemistry.","authors":"Rouven Fritzius, Paul Wiebe, Jan H Griwatz, Armin Bauer, Anika Tarasewicz, Thomas C Maier, Christian Kramer, Lucas Vidal, Christophe Aïssa, María Méndez, Hermann A Wegner","doi":"10.1039/d6ob01449f","DOIUrl":"https://doi.org/10.1039/d6ob01449f","url":null,"abstract":"Replacement of aromatic motifs with saturated bioisosteres is a proven tactic for improving the pharmacokinetic profiles of lead compounds. We present a modular continuous-flow methodology for the rapid generation of structurally diverse benzene bioisosteres, specifically targeting sp3-rich architectures such as bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, and cubane. By implementing a packed-bed flow strategy for the generation of α-keto sulfoxonium ylides as key intermediates, we developed an efficient flow-based protocol for the synthesis of 2-aminothiazoles that tolerates a wide range of thioureas and thioamides. This approach enables the rapid construction of scaffold-diverse libraries, facilitating the fine-tuning of molecular properties. Comparative analysis reveals that these bioisosteric substitutions markedly improve aqueous solubility and reduce lipophilicity relative to their phenyl counterparts, while offering a tunable scaffold to modulate molecular properties without significantly altering polar surface area or topology. This work establishes a practical synthetic framework for the systematic bioisosteric optimization of drug candidates in medicinal chemistry campaigns.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149293310","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}

引用次数: 0

Radical initiators triggered by red light irradiation. 由红光照射引发的自由基引发剂。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-29 DOI: 10.1039/d6ob01335j

Chisato Ushiyama, Rintaro Tanikawa, Ann Shinohara, Yuu Fujima, Ken-Ichi Takao, Akihiro Ogura

引用次数: 0

Chemometric amino sugar mixture analysis with a chiroptical assay array. 氨基糖混合物的化学计量分析。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-29 DOI: 10.1039/d6ob01447j

F Safia Kariapper, Christian Wolf

引用次数: 0