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Silver-catalyzed regioselective synthesis of (E)-vinyl sulfones from nitroolefins and thiophenols
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155425
Kaiyang Zhou , Xinyi Wang , Can Wang , Yunfeng Chen
{"title":"Silver-catalyzed regioselective synthesis of (E)-vinyl sulfones from nitroolefins and thiophenols","authors":"Kaiyang Zhou ,&nbsp;Xinyi Wang ,&nbsp;Can Wang ,&nbsp;Yunfeng Chen","doi":"10.1016/j.tetlet.2024.155425","DOIUrl":"10.1016/j.tetlet.2024.155425","url":null,"abstract":"<div><div>An efficient silver-catalyzed synthesis of (<em>E</em>)-vinyl sulfones was developed by denitrative radical cross-coupling of readily available thiophenols and nitroolefins. This reaction is initiated by generation of a thiyl radical or a sulfonyl radical from the thiophenol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155425"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159586","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
Cyclocondensation of o-aminophenols with α-ketothioesters in acidic media: A facile synthesis of 2-acylbenzoxazoles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155418
Kumar Kavya , Mallesha Nayak Sahana , Toreshettahally R. Swaroop , Bilagumba T. Sridhar , Kempegowda Mantelingu
{"title":"Cyclocondensation of o-aminophenols with α-ketothioesters in acidic media: A facile synthesis of 2-acylbenzoxazoles","authors":"Kumar Kavya ,&nbsp;Mallesha Nayak Sahana ,&nbsp;Toreshettahally R. Swaroop ,&nbsp;Bilagumba T. Sridhar ,&nbsp;Kempegowda Mantelingu","doi":"10.1016/j.tetlet.2024.155418","DOIUrl":"10.1016/j.tetlet.2024.155418","url":null,"abstract":"<div><div>We herein report the cyclocondensation of o-aminophenols with α-ketothioesters in acidic media for the highly regioselective synthesis of 2-acylbenzoxazoles in DMF at 80 °C. The generality of the reaction was demonstrated by using various o-aminophenols and α-ketothioesters bearing electron donating and electron withdrawing groups. In the absence and catalytic amount of acid, isomeric mixture of products: benzoxazoles and benzo[b][1,4]oxazin-2-ones were observed. Notably, in the presence of equivalent amount of acid, exclusively and regioselectively benzoxazoles are formed. The probable mechanism of formation of benzoxazoles is also presented.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155418"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159580","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
Biocatalytic synthesis of β-carboline analogues with anti-myocardial fibrosis effect using the amide bond synthetase MarA
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155410
Qing Shi , Jing-Jing Liu , Lu-Jia Wang , Hui Mao , Yu-Yang Zhang , Bo Wei , Shuang-Jun Lin , Ai-Jun Hou
{"title":"Biocatalytic synthesis of β-carboline analogues with anti-myocardial fibrosis effect using the amide bond synthetase MarA","authors":"Qing Shi ,&nbsp;Jing-Jing Liu ,&nbsp;Lu-Jia Wang ,&nbsp;Hui Mao ,&nbsp;Yu-Yang Zhang ,&nbsp;Bo Wei ,&nbsp;Shuang-Jun Lin ,&nbsp;Ai-Jun Hou","doi":"10.1016/j.tetlet.2024.155410","DOIUrl":"10.1016/j.tetlet.2024.155410","url":null,"abstract":"<div><div>The β-carboline scaffold and amide bond have great potential for drug discovery as consisting in many marketed pharmaceuticals and drug candidates. Compared to the chemical method, enzymatic synthesis of amide with nontoxicity and mild reaction conditions has received great attention. In this study, the amide bond synthetase MarA was characterized, and a series of novel amide-containing β-carboline analogues were synthesized by MarA-catalyst. Compound <strong>5b</strong> having fluorine substitution, and compound <strong>5n</strong> possessing an <em>N</em>-methyl substituent, showed excellent anti-myocardial fibrosis effects, which were found to be superior to the positive control drug, captopril. Our study provides MarA as a new green biocatalytic strategy for the synthesis of new β-carboline analogues with anti-fibrotic properties.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155410"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159581","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
Construction of functionalized naphtho[2,1-c]chromene scaffolds by Diels-Alder reaction using benzyne as dienophiles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155430
Chuanlin Lan, Yingyi Wang, Feng Sha, Xinyan Wu, Yian Cui, Yi Zheng
{"title":"Construction of functionalized naphtho[2,1-c]chromene scaffolds by Diels-Alder reaction using benzyne as dienophiles","authors":"Chuanlin Lan,&nbsp;Yingyi Wang,&nbsp;Feng Sha,&nbsp;Xinyan Wu,&nbsp;Yian Cui,&nbsp;Yi Zheng","doi":"10.1016/j.tetlet.2024.155430","DOIUrl":"10.1016/j.tetlet.2024.155430","url":null,"abstract":"<div><div>In this study, a direct synthetic methodology for the construction of dihydronaphtho[2,1-<em>c</em>]chromene scaffold derivatives has been developed. Via the benzyne-participating Diels-Alder route, the naphtho[2,1-<em>c</em>]chromene skeleton possessing promising biological activity could be efficiently furnished under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155430"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159587","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
Stereocontrolled synthesis of an α–monosubstituted α–amino acid derivative from a Ugi reaction product
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155488
Shuntaro Tsukamoto, Yuki Suzuki, Masato Oikawa
{"title":"Stereocontrolled synthesis of an α–monosubstituted α–amino acid derivative from a Ugi reaction product","authors":"Shuntaro Tsukamoto,&nbsp;Yuki Suzuki,&nbsp;Masato Oikawa","doi":"10.1016/j.tetlet.2025.155488","DOIUrl":"10.1016/j.tetlet.2025.155488","url":null,"abstract":"<div><div>We report herein an unprecedented concept for an enantiospecific synthetic strategy for α–amino acid derivatives starting from Ugi four-component coupling reaction employing chiral amine, via a chiral morpholinone intermediate. This concept was proven by the successful synthesis of (<em>S</em>)–<em>N</em>–Ac–<em>tert</em>–leucine.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155488"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150501","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
Facile Synthesis of 15N-Labeled Amino Acids Using 15N-Ammonium Salt
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155490
Kuga Arima, Kenichi Matsuda, Toshiyuki Wakimoto
{"title":"Facile Synthesis of 15N-Labeled Amino Acids Using 15N-Ammonium Salt","authors":"Kuga Arima,&nbsp;Kenichi Matsuda,&nbsp;Toshiyuki Wakimoto","doi":"10.1016/j.tetlet.2025.155490","DOIUrl":"10.1016/j.tetlet.2025.155490","url":null,"abstract":"<div><div><sup>15</sup>N-Labeled amino acids are utilized across a wide range of research fields in biology and chemistry. However, <sup>15</sup>N-labeled materials are typically not readily available, hindering broader applications despite their versatility. In this study, we developed a facile synthetic method for <sup>15</sup>N-labeled amino acid hydrochlorides, using a cost-effective and easy-to-handle <sup>15</sup>N-ammonium salt as the <sup>15</sup>N source. This method employs <sup>15</sup>N-labeled phthalimide as a key synthetic intermediate, which is subsequently coupled with hydroxy acid derivatives under Mitsunobu conditions to afford the corresponding amino acids, providing efficient access to various <sup>15</sup>N-labeled amino acids.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155490"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150504","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
Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155491
Koki Sugiura , Yuta Morishita , Yuto Shimoda , Takashi Fujimoto , Tomoyuki Fujita , Ayumi Tsutsui
{"title":"Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers","authors":"Koki Sugiura ,&nbsp;Yuta Morishita ,&nbsp;Yuto Shimoda ,&nbsp;Takashi Fujimoto ,&nbsp;Tomoyuki Fujita ,&nbsp;Ayumi Tsutsui","doi":"10.1016/j.tetlet.2025.155491","DOIUrl":"10.1016/j.tetlet.2025.155491","url":null,"abstract":"<div><div>Polyamines are important biological compounds. Mammals, including humans, biosynthesize polyamines in vivo or ingest them as food constituents. Spermidine is a reactive nucleophilic polyamine that reacts readily with aldehydes and carbonyls. In this study, a new tetrahydropyrimidine compound (MG-HSpd) is reported from the reaction of spermidine with methylglyoxal, a carbonyl stress substance produced by autoxidation of glucose. MG-HSpd was confirmed as a constituent of wheat germ crackers after the reaction of spermidine and methylglyoxal during the baking process.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155491"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150502","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
NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155489
Nilesh B. Patil , Rhutuja Patil , Ganesh U. Chaturbhuj
{"title":"NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime","authors":"Nilesh B. Patil ,&nbsp;Rhutuja Patil ,&nbsp;Ganesh U. Chaturbhuj","doi":"10.1016/j.tetlet.2025.155489","DOIUrl":"10.1016/j.tetlet.2025.155489","url":null,"abstract":"<div><div>This report describes an efficient method for synthesizing isoxazolines from aldoximes using NCBSI as a reagent. In this protocol, <em>N</em>-chloro-<em>N</em>-(phenylsulfonyl)benzene sulfonamide (NCBSI) oxidized aldoximes into nitrile oxide. The nitrile oxide underwent 1,3-dipolar cycloaddition to alkenes, giving isoxazolines in good to excellant yields. Furthermore, the precursor <em>N</em>-(phenylsulfonyl)benzene sulfonamide was recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155489"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150503","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
Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155487
Yu Bao, HaiHui Zhu, Hai Huang
{"title":"Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition","authors":"Yu Bao,&nbsp;HaiHui Zhu,&nbsp;Hai Huang","doi":"10.1016/j.tetlet.2025.155487","DOIUrl":"10.1016/j.tetlet.2025.155487","url":null,"abstract":"<div><div>Selective nonclassic propargylic substitutions have been a research focus in recent years. Herein, we developed a tandem γ-selective propargylic substitution and ring closure reaction of vinyl ethynylethylene carbonates (VEECs), efficiently synthesizing a series of 4<em>H</em>-pyran compounds. Additionally, the synthetic applications demonstrated that the products have significant synthetic potential in the synthesis of spirocyclic compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155487"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143132699","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
Multifunctional Cys labeling-directed N-terminus-selective stapling strategy development
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-24 DOI: 10.1016/j.tetlet.2025.155480
Yabo Deng , Yisheng Cao , Yi Zhou , Zhiqiang Shen , Danna Chen , Shunqing Wang , Wenjin Yan , Jian Han , Jinqi Huang
{"title":"Multifunctional Cys labeling-directed N-terminus-selective stapling strategy development","authors":"Yabo Deng ,&nbsp;Yisheng Cao ,&nbsp;Yi Zhou ,&nbsp;Zhiqiang Shen ,&nbsp;Danna Chen ,&nbsp;Shunqing Wang ,&nbsp;Wenjin Yan ,&nbsp;Jian Han ,&nbsp;Jinqi Huang","doi":"10.1016/j.tetlet.2025.155480","DOIUrl":"10.1016/j.tetlet.2025.155480","url":null,"abstract":"<div><div>Protein bioconjugation technology integrates the fields of synthetic chemistry and molecular biology, where <em>N</em>-terminal amino groups are increasingly targeted for site-specific modification strategies due to their unique properties. Herein, we report a novel approach to achieve bioconjugation of cysteine and <em>N</em>-terminal amino groups using multifunctional allyl sulfone-activated esters. The experiments were performed in a biocompatible environment (pH 7.4, 10 mM PBS, 37 °C) with universal sequence compatibility for unprotected random peptides of different lengths. Cyclic peptides show desirable late functionalization modifications (including biotin, alkynyl, and PEG et al.).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155480"},"PeriodicalIF":1.5,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150495","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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