Tetrahedron Letters最新文献

One-pot multicomponent photo-induced eosin-Y catalyzed synthesis of 2-amino oxa/thiazine derivatives 单锅多组分光诱导曙红-Y 催化合成 2-氨基氧杂/噻嗪衍生物

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-06 DOI: 10.1016/j.tetlet.2024.155339

Km Garima , Vishal Srivastava , Praveen P. Singh , Pravin K. Singh

引用次数: 0

Controllable hydrogenation of arylacetylenes with NaBH4 catalyzed by palladium nanoparticles in a fixed-bed system 固定床系统中钯纳米颗粒催化的芳基乙炔与 NaBH4 的可控氢化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-05 DOI: 10.1016/j.tetlet.2024.155355

Wei Zhang, Guohao Wu, Ying Wang, Yanhua Zhang

引用次数: 0

Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response 设计和合成基于萘二甲酰亚胺的 CO 荧光探针，实现三色检测和开关响应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-03 DOI: 10.1016/j.tetlet.2024.155357

Junyu Zhang , Guoling Li , Xuguang Zhu, Huilong Xu, Zhonghai Ni, Yun Zhao

{"title":"Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response","authors":"Junyu Zhang , Guoling Li , Xuguang Zhu, Huilong Xu, Zhonghai Ni, Yun Zhao","doi":"10.1016/j.tetlet.2024.155357","DOIUrl":"10.1016/j.tetlet.2024.155357","url":null,"abstract":"<div><div>Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586186","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

Total synthesis of natural benzoazepinoquinolinone alkaloid irrepairzepine via Au(I)-catalyzed cycloisomerization and regioselective functionalization 通过金(I)催化的环异构化和区域选择性官能化全合成天然苯并氮杂卓喹啉酮生物碱伊瑞西平

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-28 DOI: 10.1016/j.tetlet.2024.155338

Jeonghwan Park , Sujin Lee , Young Taek Han

引用次数: 0

Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates 相转移催化的芳基乙酸酯的对映选择性 α-烷基化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-28 DOI: 10.1016/j.tetlet.2024.155347

Yinuo Xiao, Zhenpeng Li, Changming Xu

引用次数: 0

Development of scalable processes to prepare a key chiral, nonracemic intermediate en route to LpxC inhibitors for Gram-negative infections 开发可扩展工艺，制备用于革兰氏阴性感染的 LpxC 抑制剂途径中的关键手性非外消旋中间体

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-24 DOI: 10.1016/j.tetlet.2024.155336

Calin D. Sferdean , Tuba Jaherun , Denis M. Sobieray , Rajendran Vairagoundar , Ronald J. VanderRoest , Valerie S. Westrick , Samir Ghosh , Kent A. Mills , Dominic Millheim , Jason D. Koch , Darryl Hester , Kamran Falahatpisheh , Daniel P. Walker

{"title":"Development of scalable processes to prepare a key chiral, nonracemic intermediate en route to LpxC inhibitors for Gram-negative infections","authors":"Calin D. Sferdean , Tuba Jaherun , Denis M. Sobieray , Rajendran Vairagoundar , Ronald J. VanderRoest , Valerie S. Westrick , Samir Ghosh , Kent A. Mills , Dominic Millheim , Jason D. Koch , Darryl Hester , Kamran Falahatpisheh , Daniel P. Walker","doi":"10.1016/j.tetlet.2024.155336","DOIUrl":"10.1016/j.tetlet.2024.155336","url":null,"abstract":"<div><div>Deaths resulting from drug-resistant Gram-negative bacterial infections are a growing public health concern. Pyridone methylsulfone hydroxamic acid LpxC inhibitors, such as <strong>1</strong>, are being developed for the treatment of serious Gram-negative infections. Carboxylic acid <strong>2</strong> is a key intermediate in the synthesis of analogs of type <strong>1</strong>. The current synthesis of <strong>2</strong> is unsuitable as a manufacturing process due to safety concerns and high cost. Two scalable and potentially lower cost processes have been developed, one based on chromatographic resolution of a novel intermediate and a second based on a classical resolution of the key intermediate <strong>3</strong>. The advantages of these new chemical approaches are illustrated in the process details described in this letter.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142552887","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

An entry to spiro-fused sultams via electrochemical brominative ipso-annulation of N-aryl alkynyl sulphonamides 通过 N-芳基炔基磺酰胺的电化学溴化异烷基化反应进入螺融舒坦类化合物领域

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-22 DOI: 10.1016/j.tetlet.2024.155330

Chada Raji Reddy , Maramoni Shivudu , Anjali Rathaur

引用次数: 0

Scalable synthesis of sulfonium and selenonium peptides for selective methyllysine reader crosslinking 用于选择性甲赖氨酸读取器交联的锍肽和硒肽的规模化合成

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-21 DOI: 10.1016/j.tetlet.2024.155332

Yingxiao Gao , Feng Feng , Mingxuan Wu

{"title":"Scalable synthesis of sulfonium and selenonium peptides for selective methyllysine reader crosslinking","authors":"Yingxiao Gao , Feng Feng , Mingxuan Wu","doi":"10.1016/j.tetlet.2024.155332","DOIUrl":"10.1016/j.tetlet.2024.155332","url":null,"abstract":"<div><div>Lysine methylation readers are an important class of proteins that bind site-specifically methylated proteins for downstream regulation. Chemical probes that crosslink lysine methylation readers are highly desired to investigate the proteins from cellular samples. We recently reported NleS<sup>+</sup>me2 (norleucine-ε-dimethylsulfonium) as dimethyllysine mimic selectively crosslinks corresponding methyllysine readers. Although the sulfonium tools exhibited great promise, the synthetic availability may limit broad applications. In order to incorporate the unnatural amino acid, <em><span>l</span></em>-Fmoc-NleSme-OH (Fmoc: fluorenyl methoxycarbonyl) was synthesized as an important building block for solid-phase peptide synthesis (SPPS) in the previous synthetic route. It took six steps with resolution of racemic mixture and radical mediated thiol-ene reaction. As a result, the synthesis was not scalable with only 4.4 % overall yield. Here we report a much-improved synthesis method so that diverse NleS<sup>+</sup>me2 peptides could be readily prepared. In addition, the new method enables preparation of selenonium peptides for methyllysine reader crosslinking. We thus believe this synthetic method will be widely used to prepare sulfonium and selenonium probes for site-selective crosslinking.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142532503","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-enalcarbenoids: Rapid access to 1,7-disubstituted indoles via [4+2] benzannulation between diazoenals and N-substituted pyrroles 铜烯碳酰胺：通过重氮烯醛和 N-取代的吡咯之间的 [4+2] 苯并annulation 快速获得 1,7-二取代的吲哚

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-19 DOI: 10.1016/j.tetlet.2024.155331

Bapurao Sudam Lad, Pratap Kumar Mandal, Rahul Chakrawarti, Sreenivas Katukojvala

引用次数: 0

An improved synthesis of alkyl AMP esters 烷基 AMP 酯的改进合成法

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-10-18 DOI: 10.1016/j.tetlet.2024.155329

Taiwo E. Esan , Charles L. Lail III , Drashti G. Daraji , Damian J. Krysan , Timothy J. Hagen

{"title":"An improved synthesis of alkyl AMP esters","authors":"Taiwo E. Esan , Charles L. Lail III , Drashti G. Daraji , Damian J. Krysan , Timothy J. Hagen","doi":"10.1016/j.tetlet.2024.155329","DOIUrl":"10.1016/j.tetlet.2024.155329","url":null,"abstract":"<div><div>Enzymes belonging to the Acyl-CoA/NRPS/Luciferase (ANL) superfamily of enzymes, are significant targets in drug development. One member of this superfamily is Acetyl-CoA Synthetase (ACS). This enzyme is an emerging target for the treatment of various infectious diseases and cancer. Alkyl AMP esters have emerged as potent inhibitors of ACS. Previous methods for synthesizing these esters often involved water-based reactions or necessitate purification through reverse phase prep-HPLC or ion-exchange chromatography. To address these challenges, we developed a new approach utilizing 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) to couple 5′-adenylic acid to the corresponding alcohol, utilizing triethylamine as the base. This method yielded primary, secondary, unsaturated, and cyclic alcohols in excellent yields. Importantly, we optimized the reaction conditions to achieve excellent yield and purity without the need for reverse phase prep-HPLC or ion exchange chromatography. Instead, purification was achieved through silica gel chromatography using Biotage ® Sfar spherical silica gel.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142532502","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