European Journal of Organic Chemistry最新文献

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Photoinduced DNA Cleavage Using Bioinspired Photostable Flavin Analogues 使用生物启发的光稳定黄素类似物进行光诱导 DNA 切割

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401001

Dipayan Mondal , Ashutosh Kumar Mishra

Inspired by the photosensitization capability of the naturally occurring flavin derivatives, viz. riboflavin (RF), flavin mononucleotide (FMN), flavin adenine dinucleotide (FAD) and their photodegradation susceptibility due to the presence of ribityl/phosphate group; the current manuscript investigates the N10‐modified flavin analogues for their reactive oxygen species (ROS) generating capability and DNA cleavage activity, when irradiated with blue light. The effectiveness of superoxide anion generating property of photoexcited flavin analogs were determined using nitro blue tetrazolium (NBT) and gallic acid quenching experiments. Among the flavin analogues studied, the simple propylflavin (PFl) was found to be most photostable and efficient in the conditions studied. The carboxyl‐flavin (10Flc) displays behavior like that of FMN while the flavin‐aspartic acid conjugate (FA) was found to show properties in between the PFl and the 10Flc.

引用次数: 0

Aryl Radicals Generated from Aryl Pinacol Boronates Modify Peptides and Proteins 芳基频哪醇硼酸酯产生的芳基自由基可修饰肽和蛋白质

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401246

Haoyu Chen , Dongqing Wu , Julian Holzinger , Rainer Götz , Dorian Didier , Anne K. Schütz , Sabine Schneider , Pavel Kielkowski

We report here a distinct reaction, which generates aryl radicals from aryl pinacol boronates under mild aqueous conditions and can be used for peptide and protein modifications. The strategy leverages the versatile reactivity of aryl pinacol boronates to form aryl radicals in presence of ammonium persulfate (APS). The formed aryl radicals insert readily into peptide disulfide bonds while tolerating other functionalities. On the protein level, the reactivity extends beyond the disulfide bonds. The methodology benefits from the accessibility of starting aryl pinacol boronates, as well as biocompatible conditions. In contrast to conventional methods used for aryl radical generation, the strategy is metal‐free, does not require photoinduction and can be readily performed under aqueous conditions. The mechanism of the reactions was investigated by radical‐trapping experiments, spectroscopic analysis and oxygen scavenging. The presented approach broadens the application of aryl pinacol boronate esters in radical reactions.

我们在此报告一种独特的反应，它能在温和的水溶液条件下从硼酸芳基频哪醇酯中生成芳基自由基，并可用于肽和蛋白质修饰。该策略利用频哪醇硼酸芳基酯的多功能反应性，在过硫酸铵（APS）存在下形成芳基自由基。形成的芳基自由基很容易插入肽的二硫键，同时还能容忍其他官能团。在蛋白质层面，反应活性超出了二硫键的范围。这种方法得益于起始芳基频哪醇硼酸盐的易获得性以及生物相容性条件。与用于生成芳基自由基的传统方法相比，该方法不含金属，不需要光诱导，可在水性条件下轻松进行。通过自由基捕获实验、光谱分析和氧清除研究了反应的机理。所提出的方法拓宽了芳基频哪醇硼酸酯在自由基反应中的应用。

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引用次数: 0

Front Cover: p-Anisil as a Versatile Catalyst for the E-to-Z Photoisomerization of Activated Alkenes - Application in Late-Stage Modification of Small Molecule Drugs, Di- and Tripeptides (Eur. J. Org. Chem. 7/2025)

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202580701

Thanh V. Q. Nguyen, Peter R. Hansen

The Front Cover illustrates expedient access to complex Z-alkenes from drugs and oligopeptides through a two-step synthetic sequence: a metal-catalyzed, directed C−H bond olefination followed by an E-to-Z photoisomerization under blue light. While the former step is established in the literature, the latter requires the development of a highly effective and robust photocatalytic system. Key to the success is the discovery of p-anisil as a versatile photocatalyst that is able to convert E-alkenes to their Z-isomers with Z/E up to >99:1. During the course of this work, 11 Z-alkenes were successfully synthesized from five drugs and two oligopeptides, thus demonstrating the practicability of the concept. More information can be found in the Research Article by T. V. Q. Nguyen and P. R. Hansen (DOI: 10.1002/ejoc.202401338). Cover by T.V.Q.N. (AstraZeneca) and Dr. Binh Phan (Essity).

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引用次数: 0

Electrochemical Alkoxylation of Benzylic C(sp3)−H Bonds 苯基C(sp3)−H键的电化学烷氧化反应

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401227

Naixuan Zhao , Geyao Xie , Miao Zheng , Shunzhen Chang , Zhenwei Zhang , Guoxue He , Yu Zhou

We report an electrochemical process for the direct alkoxylation of benzylic C(sp³)−H bonds without the need for external oxidants or metal catalysts. This environmentally friendly and sustainable synthetic strategy facilitates the alkoxylation of C(sp³)−H in benzylic groups. The approach enables the late‐stage incorporation of complex alkoxy groups into bioactive molecules, providing potential applications in the synthesis of celestolide derivatives.

我们报道了一种不需要外部氧化剂或金属催化剂的苯基C(sp3)−H键直接烷氧基化的电化学过程。这种环境友好和可持续的合成策略有利于C(sp3)−H在苯基上的烷氧基化。该方法可以在后期将复杂的烷氧基结合到生物活性分子中，为合成星形脂衍生物提供了潜在的应用。

引用次数: 0

A Meta‐Analysis of Published Brønsted Plots Supports Brønsted's “Conventional” pKa Values: 14.00 for Water and 0.00 for H+(aq)

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401135

Todd P. Silverstein, Thomas Neils

In the early 1900s, Brønsted used two different pairs of pKa values for water and the aqueous proton: He denoted 14.00 and 0.00 (respectively) as the “conventional” values, and 15.74 and −1.74 (respectively) as the “rational” values. Although the conventional values have been supported by both experiment and theory, the rational values have been employed in the vast majority of studies involving Brønsted plots up to the present day. Here we present a meta‐analysis of 67 Brønsted plots published from 1924 to 2010, revealing that rational pKa’ values more frequently appear as statistical outliers (a greater than 80 % rejection rate) compared to conventional values (a roughly 50 % rejection rate) based on Q‐tests. Furthermore, in 85 % of examined plots, the conventional points align more closely with best‐fit lines. An evaluation of Hupe and Pohl's Marcus plots also shows a somewhat better fit with the conventional rather than the rational pKa’ values. Finally, in the bond length versus pKa investigations published by Brydon et al., all the rational points were statistically rejected, whereas the conventional values were accepted. From our statistical analyses, we conclude that a convincing majority of experimental evidence from published Brønsted plots leads one to question the validity of Brønsted's rational pKa’ values for water and the aqueous proton (15.74 and −1.74, respectively).

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引用次数: 0

Ring Opening and C(ω)‐S Coupling: Nickel‐Mediated Transformation of Alicyclic Alkoxyhydroperoxides 开环和C(ω)-S偶联：镍介导的脂环烷氧氢过氧化物转化

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401198

Dmitri I. Fomenkov , Roman A. Budekhin , Olga M. Mulina , Olga A. Komarova , Mikhail M. Doronin , Yulia Yu. Belyakova , Liang‐Nian He , Ivan A. Yaremenko , Alexander O. Terent'ev

Ozonolysis of cycloalkanone semicarbazones in alcohol containing solution with the subsequent addition of nickel (II) dithiocarbamates or xanthates was found to result in ω‐xanthyl or ω‐dithiocarbamyl carboxylic acid esters. The reaction proceeds in several steps. The initial one is cycloalkanone semicarbazone ozonolysis in the presence of alcohol, which leads to alicyclic alkoxyhydroperoxide. The second step is an extraordinary interaction between the alkoxyhydroperoxide and nickel (II) dithiocarbamate or xanthate, which proceeds via alkoxy radical formation and its subsequent β‐scission, resulting in C−S coupling products. The developed method allows to obtain ω‐xanthyl or ω‐dithiocarbamyl esters in yields up to 52 % relative to the initial cycloalkanone semicarbazone.

在含醇溶液中臭氧分解环烷酮缩氨基酮，随后加入镍（II）二硫代氨基甲酸酯或黄原酸酯，得到ω-黄原酸酯或ω-二硫代氨基甲酸酯。反应分几个步骤进行。第一个是环烷酮缩氨基脲在醇的存在下臭氧分解，生成脂环烷氧双氧水。第二步是烷氧氢过氧化物与二硫代氨基甲酸镍或黄药之间的特殊相互作用，通过烷氧基自由基的形成和随后的β-裂解，产生C-S偶联产物。所开发的方法可以得到ω-黄酮或ω-二硫代氨基酯，相对于最初的环烷酮缩氨基酮，收率高达52%。

引用次数: 0

Efficient Synthesis of Indolyl Benzo[b]carbazoles via Surfactant-Type Brønsted Acid-Catalyzed Three-Component Cyclization of Ortho-Formylarylketones with Indoles

IF 2.8 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401466

Jun Yang, Tianxing Li, Hui Jin, Lixin Zhang

The surfactant-type Brønsted acid-catalyzed multi-component cascade reaction of ortho-formylarylketones with indoles was investigated in an aqueous medium for the synthesis of indolyl benzo[b]carbazoles. The reaction was carried out in the presence of dodecylbenzenesulfonic acid, which was initiated by two consecutive nucleophilic additions of indoles to the aldehyde group of ortho-formylarylketones, followed by a Friedel−Crafts-type cyclization and dehydrative aromatization. This protocol afforded the desired products in good yields under mild conditions and demonstrated a broad substrate scope.

引用次数: 0

Greening the Synthesis of 2,3‐Dihydrobenzofuran Selenides: I2/TBHP‐Promoted Selenocyclization of 2‐Allylphenols 2,3‐二氢苯并呋喃硒化物的合成：I2/TBHP‐促进2‐烯丙基酚的硒环化

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401243

Ricardo H. Bartz , Pedro S. Souza , Lucas E. B. Iarocz , Paola S. Hellwig , Prof. Raquel G. Jacob , Prof. Márcio S. Silva , Prof. Eder J. Lenardão , Prof. Gelson Perin

In this work we describe the synthesis of selenium‐containing dihydrobenzofurans through the selenocyclization reaction of 2‐allylphenols. The reaction procedure uses only an I₂/TBHP oxidant system at room temperature, enabling an efficient synthesis of 2‐[(organoselanyl)methyl]‐2,3‐dihydrobenzofurans. The products are formed immediately after the addition of the oxidant system in a mixture of 2‐allylphenol and diorganyl diselenide, in the absence of solvent, at mild experimental conditions. Furthermore, control experiments were carried out, including ⁷⁷Se NMR analyses to identify intermediates, which contributed to the elucidation of the reaction mechanism.

在这项工作中，我们描述了通过2烯丙基酚的硒环化反应合成含硒二氢苯并呋喃。该反应过程在室温下仅使用I2/TBHP氧化剂体系，可以有效合成2‐[（有机硅基）甲基]‐2,3‐二氢苯并呋喃。在没有溶剂的情况下，在温和的实验条件下，在2 -烯丙基苯酚和二有机二烯的混合物中加入氧化剂系统后，产物立即形成。此外，还进行了对照实验，包括77Se NMR分析，以确定中间体，这有助于阐明反应机理。

引用次数: 0

Synthesis of 4‐Iodoimidazole Nucleosides: A Biocatalyzed Whole Cell Approach

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202400950

Lautaro A. M. Giaimo , Dr. Leticia Lafuente , Dr. Romina N. Fernández Varela , Dr. Matías L. Nóbile , Dr. Adolfo M. Iribarren , Dr. Elizabeth S. Lewkowicz

Nucleoside analogues are biologically active drugs that are well known for their therapeutic properties. Chemical synthesis of these compounds is complex due to time constraints, contaminant methodologies, and numerous steps involved. In contrast, biocatalyzed synthesis, particularly using microorganisms, offers many advantages. In this work, we introduce the synthesis of 4‐iodoimidazole‐ribonucleoside, through a microbial transglycosylation biocatalyzed by Erwinia amylovora whole cells, selected as the optimal catalyst for this biotransformation upon evaluating our microbial collection. Parameters were analyzed to optimize the reaction, and the use of this biocatalyst in transglycosylation with other natural and non‐natural bases and different sugar donor nucleosides was also verified.

引用次数: 0

Construction of Dibenzo[a,c]Carbazoles through Oxidative Diels‐Alder Reaction of 2‐Phenyl‐1H‐Indoles and Benzynes 2 -苯基- 1H -吲哚与苯的Diels - Alder氧化反应构建二苯并[a，c]咔唑

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry

Pub Date : 2025-02-17 DOI: 10.1002/ejoc.202401241

Xinlu Xu , Yanqiao Wang , Weijie Xu , Qi Wei , Xin Ruan , Xiaofeng Zhang , Prof. Qiufeng Huang

We present here a convenient synthesis of the dibenzo[a,c]carbazoles via oxidative [4+2] Diels‐Alder cycloaddition of 2‐phenyl‐1H‐indoles with benzynes. The features of this protocol include the use of readily available raw materials, molecular oxygen as the oxidant, it being free of transition‐metal‐catalyst, and convenient method for the preparation of π‐extended dibenzo[a,c]carbazoles.

本文报道了2 -苯基- 1H -吲哚与苯的氧化[4+2]Diels−Alder环加成法合成二苯并[a，c]咔唑的方法。该方案的特点是使用了现成的原料，以分子氧为氧化剂，无过渡金属催化剂，制备π -延伸二苯并[a，c]咔唑的方法简便。

引用次数: 0

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