Quantum mechanical tunneling offers an alternative dynamical pathway to the classical (thermal) overcoming of energetic barriers, by penetrating these barriers instead. Recent years have shed light on its impact on organic synthesis in terms of kinetics, reaction outcomes, and lifetimes (and thus feasibility) of reactive intermediates or supposedly stable products. This concept article summarizes recent computational and experimental studies and illuminates how the insights from these studies, for example, regarding the concepts of tunneling control and instability, should inform synthesis design and optimization.
{"title":"Role of Quantum Tunneling in Synthetic Organic Chemistry","authors":"Tim Schleif , Ashim Nandi","doi":"10.1002/ejoc.202500656","DOIUrl":"10.1002/ejoc.202500656","url":null,"abstract":"<div><div>Quantum mechanical tunneling offers an alternative dynamical pathway to the classical (thermal) overcoming of energetic barriers, by penetrating these barriers instead. Recent years have shed light on its impact on organic synthesis in terms of kinetics, reaction outcomes, and lifetimes (and thus feasibility) of reactive intermediates or supposedly stable products. This concept article summarizes recent computational and experimental studies and illuminates how the insights from these studies, for example, regarding the concepts of tunneling control and instability, should inform synthesis design and optimization.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 45","pages":"Article e202500656"},"PeriodicalIF":2.7,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145289277","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}
Chaimaa Sadraoui , Giacomo Trapasso , Feriel Abid , Paula S. S. Lacerda , Andreia F. Sousa , Fabio Aricò
Thermoplastic polyesters (PEs), with their versatile properties, are indispensable in everyday life. However, increasing concerns about the environmental impact of fossil‐based polymers have driven research into renewable alternatives. Among bio‐based polymers, furan‐derived PEs such as poly(ethylene furanoate) (PEF) have garnered significant attention. The synthesis of PEF, as well as other similar 2,5‐furandicarboxylic acid (FDCA)‐based polymers, is mainly based on bulk polycondensation (PC) that in general requires elevated temperatures and low pressure, making the process energy‐intensive and vulnerable to thermo‐oxidative degradation. In this view, entropically driven ring opening polymerization (ED‐ROP) might represent an interesting potential alternative since it requires milder conditions and is intrinsically more atom economic. From these premises, this work focuses on developing an alternative synthetic strategy to bio‐based PEs through ED‐ROP of macrocycles derived from FDCA dimethyl ester (FDME). These macrocycles were prepared by reacting FDME with diols via pseudo‐high dilution condensation (PHDC) using dibutyltin(IV) oxide as a catalyst and cyclopentyl methyl ether as a recyclable green solvent. Isolation of the pure macrocycles is achieved by simple crystallization from the reaction mixture. Subsequent ROP of pure macrocycles is investigated as a viable route to prepare the related PEs in mild reaction conditions.
{"title":"A Greener Approach to 2,5‐Furandicarboxylate Macrocycles and their Entropically Driven Ring Opening Polymerization","authors":"Chaimaa Sadraoui , Giacomo Trapasso , Feriel Abid , Paula S. S. Lacerda , Andreia F. Sousa , Fabio Aricò","doi":"10.1002/ejoc.202500737","DOIUrl":"10.1002/ejoc.202500737","url":null,"abstract":"<div><div>Thermoplastic polyesters (PEs), with their versatile properties, are indispensable in everyday life. However, increasing concerns about the environmental impact of fossil‐based polymers have driven research into renewable alternatives. Among bio‐based polymers, furan‐derived PEs such as poly(ethylene furanoate) (PEF) have garnered significant attention. The synthesis of PEF, as well as other similar 2,5‐furandicarboxylic acid (FDCA)‐based polymers, is mainly based on bulk polycondensation (PC) that in general requires elevated temperatures and low pressure, making the process energy‐intensive and vulnerable to thermo‐oxidative degradation. In this view, entropically driven ring opening polymerization (ED‐ROP) might represent an interesting potential alternative since it requires milder conditions and is intrinsically more atom economic. From these premises, this work focuses on developing an alternative synthetic strategy to bio‐based PEs through ED‐ROP of macrocycles derived from FDCA dimethyl ester (FDME). These macrocycles were prepared by reacting FDME with diols via pseudo‐high dilution condensation (PHDC) using dibutyltin(IV) oxide as a catalyst and cyclopentyl methyl ether as a recyclable green solvent. Isolation of the pure macrocycles is achieved by simple crystallization from the reaction mixture. Subsequent ROP of pure macrocycles is investigated as a viable route to prepare the related PEs in mild reaction conditions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 45","pages":"Article e202500737"},"PeriodicalIF":2.7,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145288720","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}
Kaushal Naithani , Arka Das , Mendragutti Shireesha , Mamta Kumari , Subhadeep Roy , Subhendu Bhowmik
An ultrasound‐assisted in‐water intramolecular (3 + 2) cycloaddition reaction is reported for the synthesis of fused‐pyrrolizidine and indolizidine frameworks. This approach eliminates the need for organic solvents, harsh reagents, and high temperatures. The method's practicality is demonstrated by gram‐scale synthesis, and the anticancer properties of the resulting compounds against the triple‐negative breast cancer cell line are demonstrated.
{"title":"Ultrasound‐Assisted In‐Water [3 + 2] Cycloaddition for the Synthesis of Fused Pyrrolizidine and Indolizidine Scaffolds with Anticancer Activity","authors":"Kaushal Naithani , Arka Das , Mendragutti Shireesha , Mamta Kumari , Subhadeep Roy , Subhendu Bhowmik","doi":"10.1002/ejoc.202500690","DOIUrl":"10.1002/ejoc.202500690","url":null,"abstract":"<div><div>An ultrasound‐assisted in‐water intramolecular (3 + 2) cycloaddition reaction is reported for the synthesis of fused‐pyrrolizidine and indolizidine frameworks. This approach eliminates the need for organic solvents, harsh reagents, and high temperatures. The method's practicality is demonstrated by gram‐scale synthesis, and the anticancer properties of the resulting compounds against the triple‐negative breast cancer cell line are demonstrated.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 45","pages":"Article e202500690"},"PeriodicalIF":2.7,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145255778","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}
Oleksandr S. Liashuk, Bohdan Moroz, Kostiantyn P. Melnykov, Serhii Holovach, Dmytro Lesyk, Yaroslav Lesyk, Daniil Skrypnik, Yuliia Holota, Petro Borysko, Andrey A. Filatov, Oleksandr O. Grygorenko
The Front Cover shows a calm night sky filled with molecular constellations—gem-difluorinated fused bicyclic amines. At the center, a radiant CF2 fragment with a glowing halo symbolizes its strong influence on the compound’s properties (basicity and lipophilicity). Building silhouettes represent places from all over Ukraine that have some special significance to the authors. Labels on the buildings indicate the key methods used for the compound physicochemical characterization. More information can be found in the Research Article by O. O. Grygorenko and co-workers (DOI: 10.1002/ejoc.202500728). Cover design by O. S. Liashuk.
封面展示了一个平静的夜空，充满了分子星座——宝石二氟化融合双环胺。在中心，一个带有发光晕的辐射CF2片段象征着它对化合物性质（碱度和亲脂性）的强烈影响。建筑的剪影代表了乌克兰各地对作者有特殊意义的地方。建筑物上的标签表明了用于化合物物理化学表征的关键方法。更多信息可以在O. O. Grygorenko及其同事的研究文章中找到（DOI: 10.1002/ejoc.202500728）。封面设计：O. S. Liashuk。
{"title":"Front Cover: Basicity and Lipophilicity of gem-Difluorinated Saturated Bicyclic Amines: Advanced Building Blocks for Drug Discovery (Eur. J. Org. Chem. 45/2025)","authors":"Oleksandr S. Liashuk, Bohdan Moroz, Kostiantyn P. Melnykov, Serhii Holovach, Dmytro Lesyk, Yaroslav Lesyk, Daniil Skrypnik, Yuliia Holota, Petro Borysko, Andrey A. Filatov, Oleksandr O. Grygorenko","doi":"10.1002/ejoc.70216","DOIUrl":"10.1002/ejoc.70216","url":null,"abstract":"<p><b>The Front Cover</b> shows a calm night sky filled with molecular constellations—<i>gem</i>-difluorinated fused bicyclic amines. At the center, a radiant CF<sub>2</sub> fragment with a glowing halo symbolizes its strong influence on the compound’s properties (basicity and lipophilicity). Building silhouettes represent places from all over Ukraine that have some special significance to the authors. Labels on the buildings indicate the key methods used for the compound physicochemical characterization. More information can be found in the Research Article by O. O. Grygorenko and co-workers (DOI: 10.1002/ejoc.202500728). Cover design by O. S. Liashuk.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 45","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.70216","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145718391","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We describe a hexafluoroisopropanol (HFIP)-promoted epoxide ring-opening cyclization of readily accessible 2-[(2-substituted-1-naphthyloxy)methyl]-3-aryloxiranes, proceeding via a regioselective 7-endo cyclization at the peri (C8) position of the naphthalene ring. This transformation provides a new class of naphtho[1,8-bc]oxepine derivatives with complete regio- and diastereoselectivity. The C2 substituent on the naphthalene framework, along with the π-activating aryl group on the epoxide, plays a pivotal role in enabling the reaction. The method operates under mild conditions, tolerates a broad substrate scope, and is readily amenable to gram-scale synthesis. Moreover, the versatility of this strategy is underscored by its successful extension to the diastereoselective synthesis of oxepino[4,3,2-cd]indoles.
{"title":"Synthesis of Naphtho[1,8-bc]oxepines Through an HFIP-Promoted Peri-Selective Arene–Epoxide Cyclization","authors":"Jahnabi Das, Abhijit Gogoi, Sajal Kumar Das","doi":"10.1002/ejoc.202501042","DOIUrl":"https://doi.org/10.1002/ejoc.202501042","url":null,"abstract":"We describe a hexafluoroisopropanol (HFIP)-promoted epoxide ring-opening cyclization of readily accessible 2-[(2-substituted-1-naphthyloxy)methyl]-3-aryloxiranes, proceeding via a regioselective 7-<i>endo</i> cyclization at the <i>peri</i> (C8) position of the naphthalene ring. This transformation provides a new class of naphtho[1,8-<i>bc</i>]oxepine derivatives with complete regio- and diastereoselectivity. The C2 substituent on the naphthalene framework, along with the <i>π</i>-activating aryl group on the epoxide, plays a pivotal role in enabling the reaction. The method operates under mild conditions, tolerates a broad substrate scope, and is readily amenable to gram-scale synthesis. Moreover, the versatility of this strategy is underscored by its successful extension to the diastereoselective synthesis of oxepino[4,3,2-<i>cd</i>]indoles.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145711394","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}
A stereoselective synthesis of protected macrocyclic lactone core structure of 13 E ‐disciformycin B was accomplished in a convergent fashion employing commercially available (4 S ,5 S )‐2,2‐dimethyl‐1,3‐dioxolane‐4,5‐dicarboxylate, tiglic aldehyde and ( R )‐Roche ester. Key transformations include an Aldol reaction, CBS reduction, Takai olefination, Julia olefination, Nozaki–Hiyama–Kishi (NHK) reaction, and Yamaguchi esterification reaction.
{"title":"Stereoselective Synthesis of Protected 12‐Membered Macrolide Antibiotic 13 E ‐Disciformycin B Aglycone","authors":"Naresh Gantasala, Sankara Rao Patta, Srihari Pabbaraja","doi":"10.1002/ejoc.202500950","DOIUrl":"https://doi.org/10.1002/ejoc.202500950","url":null,"abstract":"A stereoselective synthesis of protected macrocyclic lactone core structure of 13 <jats:italic>E</jats:italic> ‐disciformycin B was accomplished in a convergent fashion employing commercially available (4 <jats:italic>S</jats:italic> ,5 <jats:italic>S</jats:italic> )‐2,2‐dimethyl‐1,3‐dioxolane‐4,5‐dicarboxylate, tiglic aldehyde and ( <jats:italic>R</jats:italic> )‐Roche ester. Key transformations include an Aldol reaction, CBS reduction, Takai olefination, Julia olefination, Nozaki–Hiyama–Kishi (NHK) reaction, and Yamaguchi esterification reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"135 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704257","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}
Herein, we report an efficient and scalable synthesis of the core skeleton of elacestrant, a selective estrogen receptor degrader used in breast cancer treatment. The present synthesis features simple synthetic transformations, involving one‐pot conversion of 6‐hydroxy‐1‐tetralone into a cyclic olefin followed by copper‐catalyzed arylation of the cyclic olefin (iodometathesis) with a diaryliodonium salt as a key strategy to achieve the core skeleton on a gram scale. This procedure was extended to the total synthesis of (±)‐elacestrant by employing two different coupling strategies: reductive amination of an aldehyde and nucleophilic substitution of a bromo compound with the core skeleton.
{"title":"Practical Synthesis of Elacestrant, an FDA‐Approved Selective Estrogen Receptor Degrader","authors":"Chandra Shekhar, Pranay Kothuri, Srivari Chandrasekhar, Kiranmai Nayani","doi":"10.1002/ejoc.202501030","DOIUrl":"https://doi.org/10.1002/ejoc.202501030","url":null,"abstract":"Herein, we report an efficient and scalable synthesis of the core skeleton of elacestrant, a selective estrogen receptor degrader used in breast cancer treatment. The present synthesis features simple synthetic transformations, involving one‐pot conversion of 6‐hydroxy‐1‐tetralone into a cyclic olefin followed by copper‐catalyzed arylation of the cyclic olefin (iodometathesis) with a diaryliodonium salt as a key strategy to achieve the core skeleton on a gram scale. This procedure was extended to the total synthesis of (±)‐elacestrant by employing two different coupling strategies: reductive amination of an aldehyde and nucleophilic substitution of a bromo compound with the core skeleton.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"386 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145704287","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}
Olesia Vasylets, Niclas Kulhanek, Michael Kirchner, Richard Göttlich
A series of novel substituted biimidazo[1,5-a]pyridine derivatives are synthesized via a robust three-step, bidirectional approach. The strategy involves an initial Negishi homocoupling of bromopicolinonitrile, followed by the formation of diketones with aryl Grignard reagents, and concludes with a double cyclization using substituted arylamines to afford a library of biimidazo[1,5-a]pyridines. Selected dimers are structurally characterized by single-crystal X-ray diffraction. In addition, the impact of substitution patterns and connectivity within the biimidazo[1,5-a]pyridine framework on their photoluminescent properties is systematically investigated. The key substitution position on imidazo[1,5-a]pyridine core for tuning optical properties is identified. Furthermore, density functional theory (DFT) calculations are conducted to complement the experimental findings, offering a deeper understanding of the electronic structure, planarity, highest occupied molecular orbital and lowest unoccupied molecular orbital properties that influence their performance as organic light-emitting materials for optoelectronic applications.
{"title":"Symmetrical Imidazo[1,5-a]pyridine Dimers as Novel Organic Light Emitters: Bidirectional Synthesis and Photoluminescence Characterization","authors":"Olesia Vasylets, Niclas Kulhanek, Michael Kirchner, Richard Göttlich","doi":"10.1002/ejoc.202500888","DOIUrl":"https://doi.org/10.1002/ejoc.202500888","url":null,"abstract":"A series of novel substituted biimidazo[1,5-<i>a</i>]pyridine derivatives are synthesized via a robust three-step, bidirectional approach. The strategy involves an initial Negishi homocoupling of bromopicolinonitrile, followed by the formation of diketones with aryl Grignard reagents, and concludes with a double cyclization using substituted arylamines to afford a library of biimidazo[1,5-<i>a</i>]pyridines. Selected dimers are structurally characterized by single-crystal X-ray diffraction. In addition, the impact of substitution patterns and connectivity within the biimidazo[1,5-<i>a</i>]pyridine framework on their photoluminescent properties is systematically investigated. The key substitution position on imidazo[1,5-<i>a</i>]pyridine core for tuning optical properties is identified. Furthermore, density functional theory (DFT) calculations are conducted to complement the experimental findings, offering a deeper understanding of the electronic structure, planarity, highest occupied molecular orbital and lowest unoccupied molecular orbital properties that influence their performance as organic light-emitting materials for optoelectronic applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145697086","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}
Zixin Huang, Qiaoli Luo, Jing Shen, Xiaoling Su, Liu Yang, Hang Li, Ao Qi, Weiguang Yang, Hua Ye
Copper‐catalyzed reactions of 2‐benzothiazolimines, terminal ynones, and sulfonyl azides afforded benzothiazolopyrimidine diastereomers. The transformation involved a tandem CuAAC/ring‐cleavage/[4 + 2] cycloaddition procedure with one‐pot synthesis under mild conditions. The benzothiazolopyrimidine diastereomers could be isolated, and their structure is confirmed by X‐ray single‐crystal diffraction.
{"title":"Synthesis of Benzothiazolopyrimidine Diastereomers Through a Copper‐Catalyzed Azide–Alkyne Cycloaddition/Ring‐Cleavage/[4 + 2] Cycloaddition Sequence","authors":"Zixin Huang, Qiaoli Luo, Jing Shen, Xiaoling Su, Liu Yang, Hang Li, Ao Qi, Weiguang Yang, Hua Ye","doi":"10.1002/ejoc.202500714","DOIUrl":"https://doi.org/10.1002/ejoc.202500714","url":null,"abstract":"Copper‐catalyzed reactions of 2‐benzothiazolimines, terminal ynones, and sulfonyl azides afforded benzothiazolopyrimidine diastereomers. The transformation involved a tandem CuAAC/ring‐cleavage/[4 + 2] cycloaddition procedure with one‐pot synthesis under mild conditions. The benzothiazolopyrimidine diastereomers could be isolated, and their structure is confirmed by X‐ray single‐crystal diffraction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"79 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145680548","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}
Emilien Mengel, Khaoula Cherkani El Hassani, Pascal Lemiere, François Dupire, Charlotte Collet, Katalin Selmeczi, Sandrine Lamandé‐Langle, Nadia Pellegrini Moïse
Multifunctional platforms are essential tools in biomedical research, particularly to develop dual imaging probes that combine, for example, fluorescence imaging (FLI) and positron emission tomography (PET). We report the design of a modular trisubstituted 1,3,5‐triazine scaffold synthesized from 2,4,6‐trichloro‐1,3,5‐triazine via sequential nucleophilic aromatic substitutions with amino‐functionalized spacers. Orthogonal protecting groups enabled selective conjugation with a cyanine dye (Cy) and a DOTA chelator for FLI and PET, respectively. The third arm was functionalized with DUPA, a prostate‐specific membrane antigen (PSMA)‐targeting pseudopeptide, via CuAAC chemistry. Despite unsuccessful attempts with Cy7 derivative (IR780), dual labeling with Cy5 and DOTA was achieved efficiently. Compound 19 exhibited optical properties comparable to commercial Cy5. These results highlight the versatility of this synthetic strategy and the potential of 19 as a dual‐modality imaging agent.
{"title":"Functionalization of 1,3,5‐Triazines: A Modular Entry to Cyanine‐Conjugated Imaging Probes","authors":"Emilien Mengel, Khaoula Cherkani El Hassani, Pascal Lemiere, François Dupire, Charlotte Collet, Katalin Selmeczi, Sandrine Lamandé‐Langle, Nadia Pellegrini Moïse","doi":"10.1002/ejoc.202500938","DOIUrl":"https://doi.org/10.1002/ejoc.202500938","url":null,"abstract":"Multifunctional platforms are essential tools in biomedical research, particularly to develop dual imaging probes that combine, for example, fluorescence imaging (FLI) and positron emission tomography (PET). We report the design of a modular trisubstituted 1,3,5‐triazine scaffold synthesized from 2,4,6‐trichloro‐1,3,5‐triazine via sequential nucleophilic aromatic substitutions with amino‐functionalized spacers. Orthogonal protecting groups enabled selective conjugation with a cyanine dye (Cy) and a DOTA chelator for FLI and PET, respectively. The third arm was functionalized with DUPA, a prostate‐specific membrane antigen (PSMA)‐targeting pseudopeptide, via CuAAC chemistry. Despite unsuccessful attempts with Cy7 derivative (IR780), dual labeling with Cy5 and DOTA was achieved efficiently. Compound 19 exhibited optical properties comparable to commercial Cy5. These results highlight the versatility of this synthetic strategy and the potential of 19 as a dual‐modality imaging agent.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145673950","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}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号