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Synthesis and evaluation of N-arylsulfonylated succinimides as activity-based probes. n -芳基磺酰基琥珀酰亚胺活性探针的合成及评价。
IF 1.4 4区 化学
Synlett Pub Date : 2025-10-01 Epub Date: 2025-05-25 DOI: 10.1055/s-0043-1775487
Jo Chvatal, Dat T Nguyen, Alexondra S Xie, William H Parsons
{"title":"Synthesis and evaluation of <i>N</i>-arylsulfonylated succinimides as activity-based probes.","authors":"Jo Chvatal, Dat T Nguyen, Alexondra S Xie, William H Parsons","doi":"10.1055/s-0043-1775487","DOIUrl":"10.1055/s-0043-1775487","url":null,"abstract":"<p><p>Activity-based protein profiling (ABPP) technology has served as a powerful platform for studying proteins for more than two decades. However, the further growth of this field depends on the development of new probe structures to expand the proportion of the proteome that can be studied using these methods. Inspired by previous reports of succinimide-containing covalent inhibitors for proteases, we synthesized a panel of potential probe structures with a succinimide reactive group and a terminal alkyne tag suitable for subsequent azide-alkyne click chemistry. Members of this panel with an <i>N</i>-arylsulfonyl linker produce labeling of both purified serine proteases as well as proteins in complex cellular lysates. We found that one of these probes labels the human rhomboid protease RHBDL2 at low micromolar concentrations and can be competed with active-site inhibitors. Our studies establish succinimide as a new reactive group for the development of activity-based probes and offer a new chemical tool for studying a class of enzymes with limited functional characterization.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"36 16","pages":"2603-2608"},"PeriodicalIF":1.4,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12478521/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145207639","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Iron-Catalyzed Stereoselective Nitrogen Atom Transfer for 1,2-cis-Selective Glycosylation. 铁催化的1,2-顺式选择性糖基化的立体选择性氮原子转移。
IF 1.4 4区 化学
Synlett Pub Date : 2025-08-20 DOI: 10.1055/a-2654-5609
Hao Xu, Dakang Zhang, Zixiang Jiang, Le Yin, Spencer I Clark, Pinzhi Wang, Jordan D Lamar, Adam M Cohen
{"title":"Iron-Catalyzed Stereoselective Nitrogen Atom Transfer for 1,2-<i>cis</i>-Selective Glycosylation.","authors":"Hao Xu, Dakang Zhang, Zixiang Jiang, Le Yin, Spencer I Clark, Pinzhi Wang, Jordan D Lamar, Adam M Cohen","doi":"10.1055/a-2654-5609","DOIUrl":"https://doi.org/10.1055/a-2654-5609","url":null,"abstract":"<p><p>This account highlights an iron-catalyzed exclusively 1,2-<i>cis</i>-selective glycosylation method for aminoglycoside synthesis. This selective nitrogen atom transfer reaction is effective for a broad range of glycosyl donors and acceptors, and it can be operated in a reiterative fashion and scaled up to the multi-gram scale. Mechanistic studies revealed a unique yet generally applicable glycosylation mechanism in which the iron catalyst activates a glycosyl acceptor and an oxidant when it facilitates the cooperative atom transfer of both moieties to a glycosyl donor in an exclusively <i>cis</i>-selective manner.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":" ","pages":""},"PeriodicalIF":1.4,"publicationDate":"2025-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12373121/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144969969","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors. 不对称异硫原脲催化合成3,4-二氢吡喃的（4+2）环加成-3-乙酸乙酯与Michael受体。
IF 1.4 4区 化学
Synlett Pub Date : 2025-08-18 DOI: 10.1055/a-2659-8340
Mario Hofer, Magdalena Piringer, Anna Scheucher, Lukas S Vogl, Mario Waser
{"title":"Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors.","authors":"Mario Hofer, Magdalena Piringer, Anna Scheucher, Lukas S Vogl, Mario Waser","doi":"10.1055/a-2659-8340","DOIUrl":"10.1055/a-2659-8340","url":null,"abstract":"<p><p>We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":" ","pages":""},"PeriodicalIF":1.4,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7618023/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144970018","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Iron-Catalyzed Cross-Electrophile Coupling. 铁催化的交叉亲电偶联。
IF 1.4 4区 化学
Synlett Pub Date : 2025-04-01 Epub Date: 2024-11-11 DOI: 10.1055/s-0043-1775420
Julius Semenya, Yuanjie Yang, Elias Picazo
{"title":"Iron-Catalyzed Cross-Electrophile Coupling.","authors":"Julius Semenya, Yuanjie Yang, Elias Picazo","doi":"10.1055/s-0043-1775420","DOIUrl":"10.1055/s-0043-1775420","url":null,"abstract":"<p><p>Metal-catalyzed cross-coupling reactions have transformed molecular synthesis. Although metal-catalyzed reactions have been used for cross-electrophile coupling reactions, they remain challenging due to homodimer formation. Recently, our group developed an iron-catalyzed cross-electrophile coupling of benzyl halides and disulfides to produce thioethers without the use of an exogenous reductant or photoredox conditions, and with undetectable levels of elimination. This Synpacts article highlights both our design strategy to obviate detrimental homodimer formation and the generality of the method.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"36 7","pages":"755-758"},"PeriodicalIF":1.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12463455/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145186735","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Development of a Triethylborane Mediated Giese Cyclization/Aldol Reaction Cascade for the Total Synthesis of Ganoapplanin. 三乙基硼烷介导的gese环化/Aldol反应级联反应的建立及全合成甘子甜素的研究。
IF 1.4 4区 化学
Synlett Pub Date : 2025-01-24 DOI: 10.1055/a-2501-4079
Nicolas Müller, Ondřej Kováč, Alexander Rode, Daniel Atzl, Thomas Magauer
{"title":"Development of a Triethylborane Mediated Giese Cyclization/Aldol Reaction Cascade for the Total Synthesis of Ganoapplanin.","authors":"Nicolas Müller, Ondřej Kováč, Alexander Rode, Daniel Atzl, Thomas Magauer","doi":"10.1055/a-2501-4079","DOIUrl":"https://doi.org/10.1055/a-2501-4079","url":null,"abstract":"<p><p>We present our synthetic endeavors towards the <i>Ganoderma</i> meroterpenoid ganoapplanin. This natural product was isolated from a <i>Ganoderma</i> fungus in 2016 and was found to be an inhibitor for T-type voltage-gated calcium channels. Our synthetic approach is based on a powerful intramolecular Giese cyclization/intermolecular aldol cascade to link the northern aromatic to the southern terpenoid fragment. This article highlights the synthetic studies that ultimately led to the successful development of the key cascade reaction, culminating in the first total synthesis of ganoapplanin. 1Introduction2Synthesis of the Southern Terpenoid Fragment3Synthesis of the Northern Terpenoid Fragment4Triethylborane Mediated Giese Cyclization/Aldol Reaction Cascades5Completion of the Total Synthesis of Ganoapplanin6Conclusion.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":" ","pages":""},"PeriodicalIF":1.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7617367/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144970013","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst 清洁反应条件下的无受体脱氢反应：以支撑镍氮氧化物为催化剂合成 2-芳基/烷基喹唑啉酮
IF 2 4区 化学
Synlett Pub Date : 2024-09-18 DOI: 10.1055/a-2388-9487
Vageesh MM, Omkar Patil, Hima PP, Raju Dey
{"title":"Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst","authors":"Vageesh MM, Omkar Patil, Hima PP, Raju Dey","doi":"10.1055/a-2388-9487","DOIUrl":"https://doi.org/10.1055/a-2388-9487","url":null,"abstract":"<p>We report here a Ni-NPs-catalyzed one-pot synthesis of 2-alkyl/aryl quinazolinone motifs <i>via</i> acceptorless dehydrogenation of alcohol, condensation of an aldehyde intermediate with 2-aminobenzamide, followed by a second dehydrogenation of the cyclized intermediate. The protocol is atom-economical and require earth-abundant Ni as the catalyst. The present report involves the annulation of 2-aminobenzamide with various types of primary alcohols, including aryl/heteroaryl methanol, and aliphatic alcohols, and produces high yields of the desired products under neat conditions. The catalyst was synthesized <i>via</i> a high-temperature pyrolysis strategy, using ZIF-8 as the sacrificial template. The Ni NPs@N-C catalyst was characterized by XPS, HR-TEM, HAADF-STEM, XRD, and ICP-MS. The catalyst is stable even in air at room temperature and displayed excellent activity in the acceptorless dehydrogenative coupling synthesis of quinazolinones and could be recycled five times without appreciable loss of its activity.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"29 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261305","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Comparison of the Effects of Stirring and Standing on Chemical Reactions 搅拌和静置对化学反应影响的比较
IF 2 4区 化学
Synlett Pub Date : 2024-09-18 DOI: 10.1055/a-2384-7220
Xianting Huang, Jianyou Zhao, Qingxu Wang, Pengkai Fang, Wei Xie, Meng Chen, Hongliang Han, Lanlan Zhang, Jiatai Zhang, Fan Wang, Zhong-Quan Liu
{"title":"Comparison of the Effects of Stirring and Standing on Chemical Reactions","authors":"Xianting Huang, Jianyou Zhao, Qingxu Wang, Pengkai Fang, Wei Xie, Meng Chen, Hongliang Han, Lanlan Zhang, Jiatai Zhang, Fan Wang, Zhong-Quan Liu","doi":"10.1055/a-2384-7220","DOIUrl":"https://doi.org/10.1055/a-2384-7220","url":null,"abstract":"<p>For hundreds of years, it seems that people have needed stirring to conduct chemical experiments. This operation can be seen everywhere in chemical, pharmaceutical, and materials laboratories and factories. People generally believe that stirring helps with processes such as material dispersion, dissolution, and collision, thereby enabling more-efficient reactions. However, why do chemical reactions that occur in Nature not require stirring? What are the facts? For this purpose, we investigated a total of 329 organic chemical reactions in eight categories and 25 types, including 26 chemical reactions magnified to gram or even kilogram levels. Under the same conditions of temperature, humidity, pressure, and reaction time, we compared the reaction yields under stirring and standing conditions. More than 600 results showed that stirring or not stirring had almost no effect on the efficiency of chemical reactions in solution. If most chemists performing reactions turned off the agitator, it would not be difficult to imagine how much electricity could be saved!</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"41 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Sustainable N-Formylation of Anilines: Harnessing Aleuritic Acid as a Renewable Formyl Source 苯胺的可持续 N-甲酰化：利用阿留申酸作为可再生甲酰基来源
IF 2 4区 化学
Synlett Pub Date : 2024-09-18 DOI: 10.1055/a-2388-9578
Hetavi A. Vadariya, Gaurav Badhani, B. Mohamed Farves, Krupa N. Boda, Subbarayappa Adimurthy
{"title":"Sustainable N-Formylation of Anilines: Harnessing Aleuritic Acid as a Renewable Formyl Source","authors":"Hetavi A. Vadariya, Gaurav Badhani, B. Mohamed Farves, Krupa N. Boda, Subbarayappa Adimurthy","doi":"10.1055/a-2388-9578","DOIUrl":"https://doi.org/10.1055/a-2388-9578","url":null,"abstract":"<p>\u0000<i>N</i>-Formylation of anilines using a renewable aleuritic acid as an eco-friendly and sustainable formylating source has been developed. <i>para</i>-Substituted anilines generally provided good yields, while moderate yields were observed with <i>meta</i>- and <i>ortho</i>-substituted derivatives. <i>In situ</i> generated formic acid through oxidative cleavage of aleuritic acid serve as a formyl source, which has been confirmed through control experiments.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"195 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Nickel-Catalyzed O-Methylation of Cinnamic Acid Using DMSO as Methyl Surrogate 镍催化肉桂酸的 O-甲基化反应（使用二甲基亚砜作为甲基替代物
IF 2 4区 化学
Synlett Pub Date : 2024-09-16 DOI: 10.1055/a-2384-6807
Hrishikesh Talukdar, Prodeep Phukan
{"title":"Nickel-Catalyzed O-Methylation of Cinnamic Acid Using DMSO as Methyl Surrogate","authors":"Hrishikesh Talukdar, Prodeep Phukan","doi":"10.1055/a-2384-6807","DOIUrl":"https://doi.org/10.1055/a-2384-6807","url":null,"abstract":"<p>A new method for the <i>O</i>-methylation of cinnamic acid employing DMSO as the methylating agent has been devised, employing a Ni-DMAP complex as catalyst along with Ag<sub>2</sub>O and dimethylamine as additives. This protocol demonstrates broad substrate compatibility and good tolerance towards various functional groups. The key advantages of this approach include the utilization of cost-effective catalysts, moderate to high yield of the products, and short reaction time.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"26 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261307","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Skeletal Reorganization: Approaches towards the Synthesis of Aza-Heterocyclic Cores 骨架重组：合成氮杂环核心的方法
IF 2 4区 化学
Synlett Pub Date : 2024-09-12 DOI: 10.1055/a-2384-6583
Dwaipayan Das, Rahul Dev Mandal, Prasun Mukherjee, Pranabes Bhattacharya, Asish R. Das
{"title":"Skeletal Reorganization: Approaches towards the Synthesis of Aza-Heterocyclic Cores","authors":"Dwaipayan Das, Rahul Dev Mandal, Prasun Mukherjee, Pranabes Bhattacharya, Asish R. Das","doi":"10.1055/a-2384-6583","DOIUrl":"https://doi.org/10.1055/a-2384-6583","url":null,"abstract":"<p>The impetuous development of the pharmaceutical industry and material science stimulates the search for new synthetic approaches and new methods for the synthesis and functionalization of aza-heterocycles; these are some of the key objectives of modern organic chemistry. As a result, an advanced method towards the synthesis of functionalized N-heterocycles that circumvents the limitations associated with traditional methods needs to be devised. In recent decades, rearrangement/reorganization reactions have emerged as a powerful tool for the efficient synthesis of the aza-heterocycle. In this illustration, we summarize some our recent efforts in the development of few complex aza-heterocyclic cores.</p> <p>1 Introduction</p> <p>2 Skeletal Rearrangement of Small Heterocycles via Domino Ring-Opening and Ring-Closing (DROC) Strategy</p> <p>3 Ru(II)-Catalyzed Skeletal Rearrangement of the Quinazoline Ring</p> <p>4 Lewis Acid Catalyzed Skeletal Rearrangement of Furans to Indolizine Cores</p> <p>5 Skeletal Rearrangement of Donor–Acceptor Cyclopropanes via Domino Ring-Opening and Ring-Closing (DROC) Strategy</p> <p>6 Lewis Acid Mediated Skeletal Rearrangement of Donor–Acceptor Spirocyclopropylpyrazolones</p> <p>7 Skeletal Rearrangement through Ring Distortion Strategy</p> <p>8 Conclusion</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"58 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210257","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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