Tetrahedron Letters最新文献_第9页

An insights into structural diversity of β-lactam scaffold towards varied medicinal applications: A comprehensive update (2020–2024) 洞察β-内酰胺支架的结构多样性，实现多种药物应用：全面更新（2020-2024 年）

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-16 DOI: 10.1016/j.tetlet.2024.155383

Ankita Garg, Teesha Thakral, Rajat Dhiman, Aman Bhalla

{"title":"An insights into structural diversity of β-lactam scaffold towards varied medicinal applications: A comprehensive update (2020–2024)","authors":"Ankita Garg, Teesha Thakral, Rajat Dhiman, Aman Bhalla","doi":"10.1016/j.tetlet.2024.155383","DOIUrl":"10.1016/j.tetlet.2024.155383","url":null,"abstract":"<div><div>β-Lactams have long been a cornerstone in the treatment of various bacterial infections, largely due to their unique structure–activity relationship with pathogenic bacteria. Significant efforts have been devoted in the literature to the development of novel β-lactam compounds and their subsequent medicinal evaluation. Moreover, the structural diversity in β-lactam derivatives has garnered significant interest in medicinal arena. Therefore, in this review thoroughly discusses the impact of structural diversity on various medicinal applications, which can be achieved through multiple synthetic approaches, including stereoselective reactions, heterocyclic fusion, regioselective modifications, and metal-catalyzed transformations. Additionally, the occurrence of functional groups such as electron-donating or electron-withdrawing groups in structurally diverse β-lactam scaffolds has been explored to assess their medicinal impact. Furthermore, β-lactam compounds have increasingly attracted interest in medicinal chemistry because of their many other remarkable biological activities. Through the analysis of stereoselectivity, heterocyclic motifs, and the impacts of functional groups, we highlight the compounds noteworthy for medicinal applications, including anti-bacterial, anti-fungal, anti-cancer, anti-oxidant, anti-diabetic, anti-viral, anti-tubercular, anti-inflammatory, analgesic and anti-malarial activity. Owing to these captivating pharmacological properties, this review provides a comprehensive update on the varied medicinal applications of β-lactam scaffolds, emphasizing a wide range of examples from 2020 to 2024.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155383"},"PeriodicalIF":1.5,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699271","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

Visible-light-induced hydrosulfonylation of alkynes driven by electron-donor–acceptor (EDA) complexes 电子供体-受体（EDA）复合物驱动的可见光诱导的炔烃氢磺化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-16 DOI: 10.1016/j.tetlet.2024.155368

Xiao-De An , Hui-Yun Wang , Long-Xue Wang , Wen-Tao Jiang , Jia-Jun Xu , Qing-Quan Sheng , Qixue Qin , Ying Fu

引用次数: 0

Electricity-driven reductive coupling reaction of imines with N-(acyloxy)phthalimides 亚胺与 N-(酰氧基)邻苯二甲酰亚胺的电驱动还原偶联反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-14 DOI: 10.1016/j.tetlet.2024.155367

Xiaoye Liu, Leilei Feng

引用次数: 0

Synthesis of (bicyclo[2.2.0]hex-1-yl)methanal and Arrhenius parameters for thermal rearrangement: Radical stabilizing effect of aldehyde substituents on highly strained CC bonds (bicyclo[2.2.0]hex-1-yl)methanal 的合成和热重排的 Arrhenius 参数：醛取代基对高应变 CC 键的辐射稳定作用

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-13 DOI: 10.1016/j.tetlet.2024.155369

Anita Nowienski , Murray G. Rosenberg , Udo H. Brinker

{"title":"Synthesis of (bicyclo[2.2.0]hex-1-yl)methanal and Arrhenius parameters for thermal rearrangement: Radical stabilizing effect of aldehyde substituents on highly strained CC bonds","authors":"Anita Nowienski , Murray G. Rosenberg , Udo H. Brinker","doi":"10.1016/j.tetlet.2024.155369","DOIUrl":"10.1016/j.tetlet.2024.155369","url":null,"abstract":"<div><div>Bicyclo[2.2.0]hexane rearranges to hexa-1,5-diene via the cyclohexane-1,4-diyl diradical. The 1-formyl substituted derivative was sought to evaluate the effect of a CHO-group on the rate of rearrangement. (Bicyclo[2.2.0]hex-1-yl)methanal was prepared for the first time in a multistep synthesis starting from hexachlorocyclopentadiene. The pivotal last step was achieved by Swern oxidation of (bicyclo[2.2.0]hex-1-yl)methanol at <em>T</em> = –60 °C. The carbon skeleton of the alcohol precursor remains intact under those conditions. Thermolysis of the aldehyde to 2-methylenehex-5-enal follows a first-order rate law between <em>T</em> = 322.85–361.51 K (<em>T</em><sub>avg</sub> = 343.30 K). Seven rate constants <em>k<sub>T</sub></em> were used to plot log <em>k<sub>T</sub></em> vs. 1/<em>T</em>, which provided the Arrhenius parameters for the rearrangement: activation energy (<em>E</em><sub>a</sub>) = 25.4 ± 1.0 kcal/mol and pre-exponential factor (<em>A</em><sub>343</sub>) = 1.66 × 10<sup>12</sup> s<sup>−1</sup>. The <em>E</em><sub>a</sub> is 10.6 kcal/mol below that of the unsubstituted archetype bicyclo[2.2.0]hexane. This sizable change in <em>E</em><sub>a</sub> reflects the radical stabilization energy of the CHO-group in 1-formylcyclohexane-1,4-diyl.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155369"},"PeriodicalIF":1.5,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699269","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

Three new macrocarpene-type sesquiterpenes and three new ent-kaurane-type diterpenoids isolated from the styles and stigmas of Zea mays L. 从玉米花柱和柱头中分离出三种新的大果萜类倍半萜和三种新的ent-kaurane类二萜。

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-13 DOI: 10.1016/j.tetlet.2024.155359

Ming Zhao , Eryan Wu , Yini Yang , Liqiu Sun , Zhichun Shi , Yingnan Zhao , Jun Li , Dan Wang

引用次数: 0

Synthetic studies on fusicoccin A: Enantioselective synthesis of the C-ring fragment 夫西可辛 A 的合成研究：C 环片段的对映选择性合成

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-12 DOI: 10.1016/j.tetlet.2024.155364

Kanae Hayashi, Masahisa Nakada

引用次数: 0

Photochemical direct C3 cyanoalkylation of quinoxalin-2(1H)-ones with cyclobutanone oxime esters under catalyst-free conditions 无催化剂条件下喹喔啉-2(1H)-酮与环丁酮肟酯的光化学直接 C3 氰烷基化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-12 DOI: 10.1016/j.tetlet.2024.155363

Jing Liu , Liting Liu , Zhiqi Lei , Xi Chen , Xia Zhao , Kui Lu

引用次数: 0

Synthesis and evaluation of cyclic peptide-dasatinib conjugates as anti-melanoma agents 作为抗黑色素瘤药物的环肽-达沙替尼共轭物的合成与评估

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-10 DOI: 10.1016/j.tetlet.2024.155365

Shaban Darwish , Dorna Davani-Davari , Shirley Tong , Rakesh Kumar Tiwari , Sun Yang , Keykavous Parang

{"title":"Synthesis and evaluation of cyclic peptide-dasatinib conjugates as anti-melanoma agents","authors":"Shaban Darwish , Dorna Davani-Davari , Shirley Tong , Rakesh Kumar Tiwari , Sun Yang , Keykavous Parang","doi":"10.1016/j.tetlet.2024.155365","DOIUrl":"10.1016/j.tetlet.2024.155365","url":null,"abstract":"<div><div>Herein, we synthesized two amphiphilic cyclic peptides, incorporating tryptophan and arginine residues, linked to dasatinib via a Cathepsin B-sensitive tetrapeptide (Gly-Phe-Leu-Gly). To mitigate steric hindrance and optimize drug release, we integrated two different linkers, succinate and glutarate, between the drug and peptide. The synthesis involved solid-phase techniques for the assembly of the peptide, followed by the coupling of the peptide on-resin with the linker, mild cleavage, and solution-phase cyclization. Conjugation of the peptide-attached linker with dasatinib was conducted in the presence of <em>N</em>-methylmorpholine and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), generating the novel prodrugs. The synthesized compounds were characterized by high-resolution mass spectrometry MALDI, and the purity was confirmed by analytical HPLC. The synthesized cyclic peptide-dasatinib conjugates containing glutarate and succinate linkers were further evaluated against human melanoma A375 cells, which exhibited IC<sub>50</sub> values of 4.2 μM and 8.8 μM, respectively. Variations in cytotoxicity could be attributed to linker properties affecting intracellular drug release or prodrug uptake.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155365"},"PeriodicalIF":1.5,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662342","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

Formal synthesis of ferruginol methyl ether via an acid-catalysed intramolecular Diels–Alder cycloaddition 通过酸催化分子内 Diels-Alder 环加成正式合成阿魏精醇甲醚

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-08 DOI: 10.1016/j.tetlet.2024.155362

Mariana Macías Alonso , Lucía S. Andrés , Joaquín González Marrero

{"title":"Formal synthesis of ferruginol methyl ether via an acid-catalysed intramolecular Diels–Alder cycloaddition","authors":"Mariana Macías Alonso , Lucía S. Andrés , Joaquín González Marrero","doi":"10.1016/j.tetlet.2024.155362","DOIUrl":"10.1016/j.tetlet.2024.155362","url":null,"abstract":"<div><div>Aromatic abietane diterpenoids, known for their wide range of biological and pharmaceutical activities, have attracted considerable interest from synthetic and medicinal chemists. Although some aromatic abietane diterpenoids are naturally abundant, many are only available in limited quantities, constraining their use in detailed biological investigations. We initiated a project to synthesize these compounds, and as our first approach, we describe the formal synthesis of ferruginol methyl ether. Starting from tiglic aldehyde (<strong>6</strong>) and 2-bromo-5-methoxybenzoic acid (<strong>11</strong>), we synthesized the triene (<strong>3</strong>) in nine steps. The key transformation involved an acid-catalysed intramolecular Diels-Alder (IMDA) cyclisation of triene (<strong>3</strong>), leading to the formation of 12-methoxy-19-norpodocarpa-4(18),8,11,13-tetraene (<strong>14</strong>) as the primary product, with an overall yield of 17.3 % across ten steps. While the yield is modest, this approach provides a novel pathway for synthesizing abietane-type compounds. We are actively exploring strategies to improve the overall yield and developing an asymmetric synthesis variant.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155362"},"PeriodicalIF":1.5,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656549","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

Synthesis of (2,3-dihydrobenzofuran-3-yl)acetic acids from salicylic aldehydes: Trimethylsilyl as traceless activating group 从水杨醛合成 (2,3-二氢苯并呋喃-3-基)乙酸：三甲基硅作为无踪活化基团

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2024-11-08 DOI: 10.1016/j.tetlet.2024.155354

Evgeny M. Buev, Polina A. Khardina, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh

引用次数: 0