{"title":"1,8-Naphthalimide derivatives as small molecules with multi-applications in chemistry and biology.","authors":"Sanaullah, Krzysztof Walczak","doi":"10.1039/d5ob00657k","DOIUrl":"https://doi.org/10.1039/d5ob00657k","url":null,"abstract":"<p><p>1,8-Naphthalimide and its derivatives have attracted attention from scientists because of their ease of synthesis, flexible structural modifications, and notable optical properties such as good fluorescence, large Stokes shifts, high quantum yields, unique photostability, and well documented biological activities. This review focuses on the modifications at the imide nitrogen and the naphthalene core of 1,8-naphthalimides through nucleophilic substitution reactions and examines their effect on the chemical, photophysical, and biological properties of these compounds. Furthermore, the wide range of applications of these compounds in the fields of chemistry and biology have also been discussed in detail. In terms of chemistry, their efficient electron transporting capabilities support their use in the development of organic light-emitting diodes (OLEDs) and high performance dyes and as ligands in the synthesis of metal complexes. In the field of biology, their outstanding capabilities in cell imaging and DNA intercalation along with their function as unique fluorescent probes underscores their utility in molecular diagnostics and targeted therapeutics. This review critically examines and bridges the diverse applications of 1,8-naphthalimides and their derivatives across the chemical and biological sciences over the past fifteen years.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144309225","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}
Geneviève F O'Keefe, Dawson J Konowalchuk, Dalida L Akl, Dennis G Hall
{"title":"Selective monophosphorylation of cyclic diols and polyols <i>via</i> hemiboronic acid catalysis.","authors":"Geneviève F O'Keefe, Dawson J Konowalchuk, Dalida L Akl, Dennis G Hall","doi":"10.1039/d5ob00813a","DOIUrl":"https://doi.org/10.1039/d5ob00813a","url":null,"abstract":"<p><p>The phosphorylation of organic molecules is a biologically essential chemical transformation. Consequently, there is high demand for methods that allow for the direct, selective, and catalytic monophosphorylation of diols and complex polyols. Due to their ability to form reversible covalent bonds with hydroxy (-OH) groups, hemiboronic acids present the unique capacity to catalytically activate diols in a nucleophilic manner. Herein, we disclose a hemiboronic acid-catalyzed monophosphorylation protocol, amenable to a variety of acyclic and cyclic diols, along with the site-selective functionalization of polyols including saccharides. Mechanistic analyses comprising of kinetic experiments and computational investigation were performed to probe for the origin of the observed site-selectivities. We propose that the observed site-selectivity originates from a difference in calculated nucleophilicity between the diol oxygens in the lower energy epimer of the reactive complex, which also exhibits a kinetically stabilizing hydrogen bonding effect with the approaching electrophile.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144300751","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}
Carla Marie Stork, Elisabeth Glöckler, Volker Derdau, Philipp Schnieders, Siegfried R Waldvogel
{"title":"Selective hydrogen isotope exchange on sulfonamides, sulfilimides and sulfoximines by electrochemically generated bases.","authors":"Carla Marie Stork, Elisabeth Glöckler, Volker Derdau, Philipp Schnieders, Siegfried R Waldvogel","doi":"10.1039/d5ob00799b","DOIUrl":"https://doi.org/10.1039/d5ob00799b","url":null,"abstract":"<p><p>We present a mild, metal-free electrochemical method to selectively add deuterium to the position α of the sulfur atom in sulfonamides, sulfilimides, and sulfoximines using a simple two-electrode setup under galvanostatic conditions. Our method is based on readily available NMR solvent DMSO-<i>d</i><sub>6</sub> as the deuterium source and reusable glassy carbon electrodes. A low current density ensures functional group tolerance and enables selective incorporation of deuterium into pharmaceutically relevant moieties. With deuterium incorporation up to 97% the method stands out as a new possibility to label molecules electrochemically without the use of toxic and expensive transition-metal catalysts.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144281750","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}
{"title":"Harnessing the reactivity of captodative radicals: photocatalytic α-pyridination of glycyl derivatives through reversible radical coupling.","authors":"Ken Yamazaki, Shuta Akimoto, Tomoya Miura","doi":"10.1039/d5ob00675a","DOIUrl":"https://doi.org/10.1039/d5ob00675a","url":null,"abstract":"<p><p>Captodative radicals that are highly stabilized by the presence of both electron-donating and electron-withdrawing groups exhibit unique reactivity in organic syntheses. These radicals are known to be less reactive towards radical-radical coupling reactions due to the presence of a shielding occupied molecular orbital. Herein we describe a photocatalytic synthetic strategy for the coupling of two different captodative radicals, which are generated from glycyl derivatives and 4-cyanopyridines. An aromatization is incorporated as the driving force after a reversible radical-radical coupling process. This method can be applied to a wide variety of peptides, providing pharmaceutically relevant pyridyl-functionalized products under mild reaction conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144281749","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}
Caitlin A McCadden, Diana P Łomowska-Keehner, Tracy Qu, Jordan Nafie, Tyler A Alsup, Jeffrey D Rudolf
{"title":"Discovery of a plant-like tridomain bifunctional <i>syn</i>-abieta-7,13-diene synthase in <i>Streptomyces</i>.","authors":"Caitlin A McCadden, Diana P Łomowska-Keehner, Tracy Qu, Jordan Nafie, Tyler A Alsup, Jeffrey D Rudolf","doi":"10.1039/d5ob00724k","DOIUrl":"10.1039/d5ob00724k","url":null,"abstract":"<p><p>Bacteria have been long proposed to harbor ancestral forms of the bifunctional terpene synthases found in plants. Recent studies described the first identification of these fused bacterial diterpene cyclases/synthases (DCSs). Using genome mining, we found candidate proteins in bacteria that were bioinformatically identified to possess both classes of terpene synthase domains. Here, we report the discovery of a plant-like tridomain bifunctional DCS from <i>Streptomyces albulus</i>. A diterpene overproduction system in <i>E. coli</i> enabled the isolation and structural elucidation of <i>syn</i>-abieta-7,13-diene by NMR, GC-MS, and VCD.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12164552/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144281748","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}
{"title":"Highly enantioselective hydrogenation of 2-pyridyl ketones enabled by Ir-<i>f</i>-phamidol catalyst.","authors":"Lei Xu, Gen-Qiang Chen, Xumu Zhang","doi":"10.1039/d5ob00833f","DOIUrl":"https://doi.org/10.1039/d5ob00833f","url":null,"abstract":"<p><p>Herein, we report a highly efficient and enantioselective Ir-<i>f</i>-phamidol catalysed hydrogenation of 2-pyridyl ketones, enabling the synthesis of chiral pyridyl-substituted secondary alcohols with exceptional enantioselectivity (up to >99% ee) and remarkable catalytic efficiency (S/C up to 10 000). The broad substrate scope, high efficiency and enantioselectivity, mild conditions, and successful gram-scale demonstration of this reaction highlight a significant advancement in chiral alcohol synthesis and underscore its practicality and industrial relevance.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144273679","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}
Bence S Nagy, Fegyverneki Dániel, Péter Szalai, András Kotschy, Márió Gyuris
{"title":"Direct catalytic synthesis of β-acylamino cyclobutanones <i>via</i> three-component Mannich reactions.","authors":"Bence S Nagy, Fegyverneki Dániel, Péter Szalai, András Kotschy, Márió Gyuris","doi":"10.1039/d4ob01543f","DOIUrl":"https://doi.org/10.1039/d4ob01543f","url":null,"abstract":"<p><p>Herein, a versatile, robust, and solvent-free method is reported for the synthesis of novel β-acylamino cyclobutanone derivatives exploiting a Cu(OTf)<sub>2</sub>/TIPSCl-promoted Mannich-type three-component approach. The present work expands the utilization of a ring-strained ketone as well as various amide derivatives as amine equivalents, which has remained relatively underexplored due to their low reactivity profile. Following a rapid optimization of the reaction conditions, a relevant set of β-acylamino cyclobutanone derivatives has been designed and generated. Furthermore, the synthetic utility of our process has been demonstrated <i>via</i> a dual Au(I)/Ag(I)-catalyzed intramolecular hydroxygenation reaction to showcase a representative post-Mannich transformation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144273678","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}
{"title":"Indole-2-carboxamide: a versatile synthetic handle for the synthesis of diversely substituted polycyclic indole structures.","authors":"Akshay Kamble, Priyanka Deore, Vanshika Agrawal, Adesh Chauhan, Haneesha Gulipelli, Satyasheel Sharma","doi":"10.1039/d5ob00761e","DOIUrl":"https://doi.org/10.1039/d5ob00761e","url":null,"abstract":"<p><p>Indoles are among the most important N-heterocycles found in natural products, with a wide range of biological and pharmacological properties. The synthesis of naturally occurring complex indole derivatives as well as bioactive synthetic molecules has progressed tremendously. Since many of the bioactive, naturally occurring indole molecules possess polycyclic frameworks, it became essential to develop these scaffolds. In this context, indole derivatives have been utilized as precursors for the synthesis of many important polycyclic indole frameworks. These polycyclic indole molecules also include a fused indole motif. In this regard, there are many fused indole ring systems which can be accessed by indole-2-carboxamide as a key precursor through intramolecular and intermolecular cyclization reactions. This review summarizes the synthetic advancements for the construction of polycyclic fused indole molecules, which have indole-2-carboxamide as a synthetic precursor, and also discusses the synthetic potential and perspective of this essential scaffold. Furthermore, the reaction mechanism of the formation of various fused polycyclic indoles has also been discussed.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144273680","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}
Damian Jagleniec, Katarzyna Sęktas, Łukasz Dobrzycki, Miłosz Ludwinek, Anna Nasulewicz-Goldeman, Joanna Wietrzyk, Jan Romański
{"title":"Multifunctional supramolecular receptors: aqueous ion recognition, HCl sensing and cytotoxic potential.","authors":"Damian Jagleniec, Katarzyna Sęktas, Łukasz Dobrzycki, Miłosz Ludwinek, Anna Nasulewicz-Goldeman, Joanna Wietrzyk, Jan Romański","doi":"10.1039/d5ob00585j","DOIUrl":"https://doi.org/10.1039/d5ob00585j","url":null,"abstract":"<p><p>We describe the design, synthesis, and binding behavior of three supramolecular receptors aimed at selective ion-pair recognition in aqueous and organic media. Incorporating squaramide and tertiary amine functionalities, these receptors exhibit strong affinities for anions and ion pairs, especially in the presence of sodium cations. Notably, protonation of the tertiary amine in receptor 1 significantly enhances its water solubility and anion-binding affinity by increasing the acidity of the squaramide protons, thereby strengthening interactions with chloride anions even in competitive, water-rich environments. Receptor 3, modified with a pyrene unit, functions as a fluorescence sensor capable of extracting chloride from aqueous phases into organic solvents, indicating potential applications in molecular sensing and ion transport. Preliminary biological assays reveal that these compounds exhibit cytotoxic activity comparable to cisplatin on specific cell lines, suggesting promise as therapeutic agents. This study highlights the utility of multifunctional receptors in aqueous ion-pair recognition and transport, with implications for both environmental and biomedical applications.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144273681","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}
Shi-Kai Jiang, Heng Lei, Ji-Hang Shen, Xi Shen, Xiao-Jun Ji, Zhi-Gang Zhang
{"title":"Biosynthesis of 5-hydroxymethyl-2-furancarboxylic acid from 5-hydroxymethylfurfural <i>via</i> new whole-cell biocatalysts.","authors":"Shi-Kai Jiang, Heng Lei, Ji-Hang Shen, Xi Shen, Xiao-Jun Ji, Zhi-Gang Zhang","doi":"10.1039/d5ob00783f","DOIUrl":"https://doi.org/10.1039/d5ob00783f","url":null,"abstract":"<p><p>The selective oxidation of biomass-derived 5-hydroxymethylfurfural (HMF) to value-added furan compounds presents significant challenges due to the inherent high reactivity of HMF. In this study, two microorganisms were identified as whole-cell biocatalysts for the synthesis of 5-hydroxymethylfuroic acid (HMFCA) from HMF. The cells of <i>Pseudochrobactrum</i> sp. B2L and <i>Lysinibacillus</i> sp. B2P showed susceptibility to low pH conditions that result from the accumulation of the HMFCA product. Nevertheless, they exhibited high tolerance to the HMF substrate and the 2,5-bis(hydroxymethyl)furan (BHMF) intermediate during the reaction process. Under optimized conditions, a concentration of 200 mM HMF was nearly completely converted into HMFCA, achieving a yield of 99% by utilizing the cells of both microorganisms. Upon increasing the HMF substrate concentration to 300 mM, HMFCA yields of up to 80% were obtained, demonstrating excellent catalytic performance. The identification of <i>Pseudochrobactrum</i> sp. B2L and <i>Lysinibacillus</i> sp. B2P as biocatalysts for the synthesis of HMFCA expands the biocatalytic repertoire available for the sustainable production of bio-based chemicals from HMF. Furthermore, these findings contribute valuable insights for the future identification of related enzymes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144264851","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}