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Regulation of a chromenylium fluorophore with a built-in recognition site for the detection of sulfite† 调节一个内置识别位点的亚硫酸盐检测的铬荧光团。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-25 DOI: 10.1039/D5OB00504C
Anqi Hou, Yuanyuan Wu, Yumeng Liu, Chang Liu, Huirong Yao and Xianshun Zeng
{"title":"Regulation of a chromenylium fluorophore with a built-in recognition site for the detection of sulfite†","authors":"Anqi Hou, Yuanyuan Wu, Yumeng Liu, Chang Liu, Huirong Yao and Xianshun Zeng","doi":"10.1039/D5OB00504C","DOIUrl":"10.1039/D5OB00504C","url":null,"abstract":"<p >A double charged cationic pyridinium-fused chromenylium analogue <strong>DMCQ</strong> with an acceptor–π–acceptor (A–π–A) electronic structure was designed and prepared for the sensitive and selective detection of SO<small><sub>3</sub></small><small><sup>2−</sup></small>. Undergoing a Michael addition reaction with SO<small><sub>3</sub></small><small><sup>2−</sup></small> at the built-in pyridinium moiety in the chromenylium fluorophore, the π-electron structure of the chromenylium skeleton transferred from an (A–π–A) to (A–π–D) system along with a prominent fluorescence enhancement. Based on this specific addition reaction, the <strong>DMCQ</strong> probe exhibits high selectivity for the detection of SO<small><sub>3</sub></small><small><sup>2−</sup></small> over other biologically related species within a wide pH range (4–10). As the highly electron-deficient nature of the pyridinium-fused chromenylium accelerated the reaction with SO<small><sub>3</sub></small><small><sup>2−</sup></small>, the probe presented a rapid response time (60 s), together with high sensitivity (33 nM). Besides, <strong>DMCQ</strong> could not only image SO<small><sub>3</sub></small><small><sup>2−</sup></small> in living cells but also monitor SO<small><sub>3</sub></small><small><sup>2−</sup></small> in food and water samples with a satisfactory recovery of 81.30–112.89%.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5148-5153"},"PeriodicalIF":2.9,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143958520","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
A formal [4 + 1] annulation incorporating styrylogous aldol condensation to access functionalized 2-styryl-benzofurans† 一种正式的[4 + 1]环化反应，结合苯乙烯醛缩合反应获得功能化的2-苯乙烯苯并呋喃。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-25 DOI: 10.1039/D5OB00348B
Manyam Subbi Reddy, Kandivalasa Kamala and Surisetti Suresh
{"title":"A formal [4 + 1] annulation incorporating styrylogous aldol condensation to access functionalized 2-styryl-benzofurans†","authors":"Manyam Subbi Reddy, Kandivalasa Kamala and Surisetti Suresh","doi":"10.1039/D5OB00348B","DOIUrl":"10.1039/D5OB00348B","url":null,"abstract":"<p >Despite the well-established aldol reaction and its vinylogous variants, the styrylogous version has been scarcely reported. Herein, we have introduced a styrylogous aldol condensation reaction. A novel base-mediated formal [4 + 1] annulation, integrating <em>O</em>-allylation and styrylogous aldol condensation, has been disclosed. This transformation involves <em>ortho</em>-hydroxyaryl aldehydes/ketones in conjunction with distally-activated cinnamyl (pseudo)halides. The presented transition metal-free process forms C–O and C<img>C bonds, enabling the synthesis of functionalized 2-styryl-benzofuran derivatives in moderate to good yields. The application potential of the developed method has been demonstrated in the efficient syntheses of 2-aminostyryl-benzofuran derivatives, which have proven to act as potent inhibitors for Aβ fibril formation related to Alzheimer's disease (AD).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5096-5100"},"PeriodicalIF":2.9,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955960","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
Synthesis of 1,3,4-thiadiazoles from elemental sulfur via three-component cyclization under metal-free conditions† 无金属条件下单质硫三组分环化合成1,3,4-噻二唑。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-25 DOI: 10.1039/D5OB00554J
Chuanquan Chu, Yu Liu, Min Mao, Dahan Wang, Jinbing Liu, Huaixin Wei, Mingming Yu and Jinhui Cai
{"title":"Synthesis of 1,3,4-thiadiazoles from elemental sulfur via three-component cyclization under metal-free conditions†","authors":"Chuanquan Chu, Yu Liu, Min Mao, Dahan Wang, Jinbing Liu, Huaixin Wei, Mingming Yu and Jinhui Cai","doi":"10.1039/D5OB00554J","DOIUrl":"10.1039/D5OB00554J","url":null,"abstract":"<p >In this work, we demonstrate the synthesis of a variety of 2,5-disubstituted 1,3,4-thiadiazoles in 28–85% yields <em>via</em> three-component cyclization of 2-methylquinolines, arylhydrazides, and S powder under metal-free conditions. This approach stands out due to its broad substrate scope, excellent functional group tolerance, additive-free nature, base-free nature, easy operation, and simple reaction system. This work offers a simple, concise, and convenient pathway for the assembly of a variety of 1,3,4-thiadiazoles, which is complementary to previous methods.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5101-5105"},"PeriodicalIF":2.9,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955326","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
cis-Amide promotion in α-ABpeptoid foldamers via triazolium side chains. 顺酰胺通过三唑侧链促进α- ab肽样折叠体。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-25 DOI: 10.1039/d5ob00355e
Jungyeon Kim, Ganesh A Sable, Kang Ju Lee, Hyun-Suk Lim, Min Hyeon Shin
{"title":"<i>cis</i>-Amide promotion in α-ABpeptoid foldamers <i>via</i> triazolium side chains.","authors":"Jungyeon Kim, Ganesh A Sable, Kang Ju Lee, Hyun-Suk Lim, Min Hyeon Shin","doi":"10.1039/d5ob00355e","DOIUrl":"https://doi.org/10.1039/d5ob00355e","url":null,"abstract":"<p><p>Precise control of amide bond rotation is crucial for the construction of well-defined three-dimensional structures in peptidomimetic foldamers. We previously introduced α-ABpeptoids as a new class of peptoid foldamers incorporating backbone chirality and demonstrated their folding propensities. However, the rotational isomerism of their backbone amide bonds remains largely unregulated. Here, we report the development of α-ABpeptoids functionalized with triazolium side chains that promote <i>cis</i>-amide bond formation. A series of α-ABpeptoid oligomers bearing neutral triazole or cationic triazolium side chains were synthesized and analyzed by NMR and circular dichroism spectroscopy. The triazolium-functionalized α-ABpeptoids exhibited a strong preference for <i>cis</i>-amide geometry, resulting in enhanced conformational homogeneity. These findings establish triazolium substitution as an effective strategy for conformational control in α-ABpeptoid foldamers, expanding their utility in the design of structured, functional peptidomimetics.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955083","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
Enhanced glucose regulation potential of C-peptide mimics† 增强c肽模拟物的葡萄糖调节潜能。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-25 DOI: 10.1039/D5OB00318K
Alpana Boruah, Nazim Uddin Afzal, Sayari Saha, Anusmrita Mazumdar, Dibyajyoti Ozah, Thaneswar Bora, Panchami Prabhakaran, Prasenjit Manna and Arup Roy
{"title":"Enhanced glucose regulation potential of C-peptide mimics†","authors":"Alpana Boruah, Nazim Uddin Afzal, Sayari Saha, Anusmrita Mazumdar, Dibyajyoti Ozah, Thaneswar Bora, Panchami Prabhakaran, Prasenjit Manna and Arup Roy","doi":"10.1039/D5OB00318K","DOIUrl":"10.1039/D5OB00318K","url":null,"abstract":"<p >The connecting peptide (C-peptide), once relegated as an epiphenomenon in insulin biosynthesis, has now been recognized for its capacity to instigate molecular effects along with important physiological functions. These findings suggest that C-peptide is a hormonally active molecule responsible for controlling a number of diabetes-related complications, in addition to proinsulin processing. Notably, it demonstrates cellular responsiveness and acts as a robust biomarker for beta cell functions, with a half-life longer than that of insulin. Herein, we investigated the effect of some synthetic C-peptide mimics on glucose homeostasis, specifically focusing on glucose uptake, GLUT4 translocation and associated membrane trafficking processes. The glucose utilization potential of some of the C-peptide mimics in L6 muscle myotubes was significantly better than that of the human C-peptide. One of the synthesized C-peptide mimics, <strong>CP8</strong>, showed glucose metabolism akin to insulin, including potential for Akt phosphorylation and IRβ autophosphorylation. Also, it showed the ability to mitigate intramolecular reactive oxygen species production. The results obtained here highlight the potential of C-peptide mimics on glucose metabolism, as well as interaction with Akt and IRβ, positioning them as promising candidates for future diabetes research.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5163-5173"},"PeriodicalIF":2.9,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143957292","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
Investigation of the factors influencing the selectivity and response times of glyoxal-selective probes† 乙二醛选择性探针的选择性和响应时间的影响因素研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-25 DOI: 10.1039/D5OB00366K
Yuanyuan Wu, Chang Liu, Huirong Yao, Song He, Liancheng Zhao and Xianshun Zeng
{"title":"Investigation of the factors influencing the selectivity and response times of glyoxal-selective probes†","authors":"Yuanyuan Wu, Chang Liu, Huirong Yao, Song He, Liancheng Zhao and Xianshun Zeng","doi":"10.1039/D5OB00366K","DOIUrl":"10.1039/D5OB00366K","url":null,"abstract":"<p >In this work, four <em>o</em>-phenylenediamine-conjugated fluorescent probes <strong>1–4</strong> with different substituents on the amino group have been designed and prepared to investigate the factors influencing the selectivity and response times of the probes toward glyoxal (GO). The introduced substituted groups, including <em>n</em>-propyl, iso-propyl, <em>tert</em>-butyl, and phenyl, <strong>1–4</strong> displayed sufficient selectivity toward GO. Due to the fact that GO normally exists in a hydrated state in aqueous media, the reaction rates between <strong>1–4</strong> and GO exhibited significant deviation from the steric hindrance effects of most organic reactions. Compounds <strong>3</strong> and <strong>4</strong> with bulky substituted groups presented faster reaction rates with GO than those of compounds <strong>1–2</strong>. To further elucidate the properties of these compounds, we selected compound <strong>3</strong> as the representative compound, because of its best selectivity and fast response time, for detailed investigation of the recognition behaviors both in aqueous solution and in living cells. Probe <strong>3</strong> exhibited high selectivity and high sensitivity toward GO with a large Stokes shift (&gt;100 nm), making it highly suitable for <em>in vivo</em> imaging research.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5139-5147"},"PeriodicalIF":2.9,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951922","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
Photoinduced N-heterocyclic nitrenium-catalyzed single electron reduction of α-chloro esters for phenanthridine synthesis† 光诱导n -杂环氮催化α-氯酯单电子还原合成菲咯啶。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-24 DOI: 10.1039/D5OB00530B
Ling Zhou, Xiao-Xue Pei, Wei Gong, He Sheng and Zhu-Sheng Yang
{"title":"Photoinduced N-heterocyclic nitrenium-catalyzed single electron reduction of α-chloro esters for phenanthridine synthesis†","authors":"Ling Zhou, Xiao-Xue Pei, Wei Gong, He Sheng and Zhu-Sheng Yang","doi":"10.1039/D5OB00530B","DOIUrl":"10.1039/D5OB00530B","url":null,"abstract":"<p >Visible-light photoredox catalysis has revolutionized synthetic methodologies by enabling sustainable radical-mediated transformations under mild conditions. Herein, we report a catalytic protocol employing N-heterocyclic nitrenium (NHN) iodide salts to drive the photoreduction of α-chloro esters, generating alkyl radicals that participate in annulation with 2-isocyanobiaryls for the modular synthesis of phenanthridine derivatives. This approach is characterized by easily available NHNs and operational simplicity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5122-5125"},"PeriodicalIF":2.9,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956292","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
Visible-light-promoted phosphine-mediated synthesis of thioesters and thioalkynes from sodium arylsulfinates† 可见光促进膦介导的芳基亚磺酸钠合成硫酯和硫代炔。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-24 DOI: 10.1039/D5OB00453E
Sen Chen, Yu Yu and Min Chen
{"title":"Visible-light-promoted phosphine-mediated synthesis of thioesters and thioalkynes from sodium arylsulfinates†","authors":"Sen Chen, Yu Yu and Min Chen","doi":"10.1039/D5OB00453E","DOIUrl":"10.1039/D5OB00453E","url":null,"abstract":"<p >We herein report a facile method to access thioesters and thioalkynes <em>via</em> a visible-light-promoted phosphine-mediated radical deoxyfunctionalization of sodium arylsulfinates with activated acids and iodoalkynes, respectively. The introduction of acid additives could facilitate the generation of arylthiyl radicals <em>via</em> tuning the equilibrium between arylsulfinate salts and the corresponding sulfinic acids, which favours the formation of thioesters while disfavouring the formation of thioalkynes. This protocol also features readily available starting materials, good functional group tolerance and practical applicability, for example, in the late-stage functionalization of non-steroidal anti-inflammatory drugs (NSAIDs).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5174-5181"},"PeriodicalIF":2.9,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951140","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
Concise organocatalyzed epoxidation based total synthesis of (−)- and (+)-trans-posticlures and (−)-(6Z,9Z,4S,5S)-trans-4,5-epoxynonadeca-6,9-diene† 基于简洁有机催化环氧化的(-)-和(+)-反式位姿和(-)-(6Z,9Z,4S,5S)-反式4,5-环氧壬二烯的全合成
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-24 DOI: 10.1039/D5OB00597C
Rodney A. Fernandes and Gulenur N. Khatun
{"title":"Concise organocatalyzed epoxidation based total synthesis of (−)- and (+)-trans-posticlures and (−)-(6Z,9Z,4S,5S)-trans-4,5-epoxynonadeca-6,9-diene†","authors":"Rodney A. Fernandes and Gulenur N. Khatun","doi":"10.1039/D5OB00597C","DOIUrl":"10.1039/D5OB00597C","url":null,"abstract":"<p >A concise, flexible and efficient organocatalytic strategy has been developed for the enantioselective synthesis of (−)-<em>trans</em>- and (+)-<em>trans</em>-posticlures, along with (−)-(6<em>Z</em>,9<em>Z</em>,4<em>S</em>,5<em>S</em>)-<em>trans</em>-4,5-epoxynonadeca-6,9-diene which are remarkable natural <em>trans</em>-epoxide pheromones. The key transformations in this approach involve an organocatalyzed asymmetric Jørgensen epoxidation and stereoselective (<em>Z</em>)-Wittig olefination. Notably, the Jørgensen epoxidation step ensures excellent enantiopurity (up to 97% ee) in the synthesis of the target pheromone antipodes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 21","pages":" 5159-5162"},"PeriodicalIF":2.9,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955220","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
Red-shifted photoredox generation and trapping of alkyl radicals towards bioorthogonality. 红移光氧化还原的产生和向生物正交的烷基自由基的捕获。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-23 DOI: 10.1039/d5ob00476d
David Montoto, Uxía Deus-Lorenzo, María Tomás-Gamasa, José L Mascareñas, Mauro Mato
{"title":"Red-shifted photoredox generation and trapping of alkyl radicals towards bioorthogonality.","authors":"David Montoto, Uxía Deus-Lorenzo, María Tomás-Gamasa, José L Mascareñas, Mauro Mato","doi":"10.1039/d5ob00476d","DOIUrl":"https://doi.org/10.1039/d5ob00476d","url":null,"abstract":"<p><p>The photocatalytic generation and trapping of alkyl radicals is a powerful synthetic tool in organic chemistry, but it remains underexplored in biological settings. Here, we present two photoredox systems that leverage green- or red-light irradiation for the activation and subsequent Giese coupling of redox-active alkyl phthalimide esters. Besides utilizing mild low-energy light sources, these reactions operate with biocompatible BnNAH or NADH as electron donor. Notably, they display compatibility with air, water and biologically relevant conditions, including cell-culture media or even cell lysates. This work marks a significant step towards integrating synthetic alkyl-radical chemistry into biological settings.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951657","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
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