Tetrahedron最新文献_第3页

[3 + 2] cycloaddition of quinazoline-derived azomethine imines with electron-deficient alkenes to access functionalized fused tricyclic tetrahydropyrazolo[1,5-c]quinazoline frameworks [3 + 2]喹唑啉衍生的亚甲基亚胺与缺电子烯烃的环加成得到功能化的三环四氢吡唑啉[1,5-c]喹唑啉框架

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-29 DOI: 10.1016/j.tet.2025.134749

Kai-Kai Wang , Ya-Fei Li , Ran Bi , Xue-Hao Wang , Xue Xue , Peng Lu , Yue-Yao Ma , Na-Na Zhao , Guo-Yi Yan

{"title":"[3 + 2] cycloaddition of quinazoline-derived azomethine imines with electron-deficient alkenes to access functionalized fused tricyclic tetrahydropyrazolo[1,5-c]quinazoline frameworks","authors":"Kai-Kai Wang , Ya-Fei Li , Ran Bi , Xue-Hao Wang , Xue Xue , Peng Lu , Yue-Yao Ma , Na-Na Zhao , Guo-Yi Yan","doi":"10.1016/j.tet.2025.134749","DOIUrl":"10.1016/j.tet.2025.134749","url":null,"abstract":"<div><div>A classical Huisgen 1,3-dipolar cycloaddition reaction between quinazoline-derived azomethine imines and electron-deficient alkenes has been developed. This reaction offers a dearomatization strategy for the direct synthesis of functionalized fused tricyclic tetrahydropyrazolo[1,5-<em>c</em>]quinazoline frameworks, which contain two contiguous stereocenters. The reaction proceeds under mild conditions and achieves high yields (95–98 %), with excellent regio- and diastereoselectivity (up to >25:1 dr). Furthermore, this protocol is characterized by the use of easily available starting materials, a broad substrate scope, good functional group compatibility, straightforward operation, and 100 % atom economy. Additionally, the synthetic utility of this methodology was further demonstrated through synthetic transformations. The structure and relative configuration of the typical product were unambiguously established by single-crystal X-ray diffraction analysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134749"},"PeriodicalIF":2.1,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144166461","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

Transition metal-free direct C(sp2)-H thiocyanation of 2-iminothiazolines at room temperature 室温下2-亚氨基噻唑啉的无金属直接C(sp2)-H硫氰化反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-28 DOI: 10.1016/j.tet.2025.134756

Umang Pithadiya , Naimish Dobariya , Vaibhav D. Prajapati , Ronak V. Prajapati , Vishal B. Purohit , Vicky Jain , Sharad C. Karad

引用次数: 0

Drimane based substituted pyrano-oxepines from labdane diterpene sclareol; stereoselective synthesis, molecular docking simulations and in silico ADMET prediction studies 从唇丹二萜戊二醇提取的吡喃基取代氧平类化合物立体选择合成，分子对接模拟和ADMET预测研究

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-28 DOI: 10.1016/j.tet.2025.134758

Gulzar Hussain , Umar Ul Islam , Yogesh P. Bharitkar , Avinash Madhesiya , Tejender S. Thakur , Syed Khalid Yousuf

{"title":"Drimane based substituted pyrano-oxepines from labdane diterpene sclareol; stereoselective synthesis, molecular docking simulations and in silico ADMET prediction studies","authors":"Gulzar Hussain , Umar Ul Islam , Yogesh P. Bharitkar , Avinash Madhesiya , Tejender S. Thakur , Syed Khalid Yousuf","doi":"10.1016/j.tet.2025.134758","DOIUrl":"10.1016/j.tet.2025.134758","url":null,"abstract":"<div><div>Sclareol, a labdane diterpene alcohol, has been studied for the stereoselective synthesis of drimane-based aryl, alkyl, and heteroaryl substituted pyrano-oxepines. The synthesis process involves two main steps: first, generating a homoallylic alcohol from sclareol, followed by TMSOTf-mediated Prins cyclization using various aldehydes. This approach is characterized by its broad substrate scope, short reaction times, and complete stereoselectivity. The synthesized derivatives were fully characterized using a various spectroscopic techniques, including 1D and 2D NMR, high-resolution mass spectrometry (HRMS), and X-ray diffraction. To investigate their potential as anticancer agents, all synthesized compounds underwent molecular docking studies against BRCA1 proteins, which are key targets in breast cancer therapy. The analysis revealed that the derivatives exhibited better binding affinity values, ranging from −6.6 to −8.3 kcal/mol, compared to the parent molecule sclareol, which had a binding affinity of −5.6 kcal/mol. Notably, compound <strong>14</strong> displayed the most favorable interaction with a binding affinity of −8.3 kcal/mol. Furthermore, ADMET studies and normal mode analysis (NMA) simulations indicated that the synthesized drimane-based pyrano[3,4]oxepines possess favorable drug-like properties and structural stability. These compounds exhibit ideal physicochemical characteristics, excellent oral bioavailability, promising pharmacokinetic behavior, and minimal toxicity risk. These results highlight the potential of drimane-based pyrano[3,4]oxepine derivatives as promising candidates for the development of effective breast cancer inhibitors.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134758"},"PeriodicalIF":2.1,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144184517","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 (hydroxymethyl)(methylsulfonyl)pyrano[3,2-b]pyran derivatives using a basic ionic liquid, [(HOCH2)2C(CH3)NH3+][HCOO−], as a green catalyst 以碱性离子液体[(HOCH2)2C(CH3)NH3+][HCOO−]为绿色催化剂合成（羟甲基）（甲基磺酰基）吡喃[3,2-b]吡喃衍生物

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-27 DOI: 10.1016/j.tet.2025.134755

Farhad Shirzaei, Hamid Reza Shaterian

引用次数: 0

Near-infrared fluorescent probe for real-time monitoring of sulfhydryl dynamics in acute alcoholic liver injury models 近红外荧光探针实时监测急性酒精性肝损伤模型巯基动力学

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-27 DOI: 10.1016/j.tet.2025.134750

Qiyu Chen , Qian Liu , Ruipeng Shen , Zhiyuan Wang , Tao Ma , Baoxin Zhang , Dongzhu Duan

{"title":"Near-infrared fluorescent probe for real-time monitoring of sulfhydryl dynamics in acute alcoholic liver injury models","authors":"Qiyu Chen , Qian Liu , Ruipeng Shen , Zhiyuan Wang , Tao Ma , Baoxin Zhang , Dongzhu Duan","doi":"10.1016/j.tet.2025.134750","DOIUrl":"10.1016/j.tet.2025.134750","url":null,"abstract":"<div><div>Acute alcoholic liver injury (AALI) is characterized by liver inflammation and dysfunction, primarily due to excessive alcohol consumption, which triggers oxidative stress and fatty degeneration. Thiols play a crucial role in mitigating oxidative stress-induced cell damage, owing to their antioxidant and detoxifying properties. Consequently, accurate monitoring of intracellular thiol levels is essential for assessing the severity and progression of AALI. To achieve this, we developed a series of near-infrared fluorescent probes by conjugating 2, 4-dinitrobenzenesulfonyl chloride with a dicyanoisophorone core. Comprehensive analysis revealed <strong>DIP-Br</strong> as the optimal probe, demonstrating exceptional thiol sensitivity, high selectivity, and rapid detection capability under physiological pH conditions. We then applied <strong>DIP-Br</strong> in cellular oxidative stress models and AALI mouse models, which revealed significant fluctuations in thiol levels. This finding underscores the probe's ability to monitor dynamic redox processes in vivo, providing valuable insights into the molecular mechanisms of AALI. Furthermore, <strong>DIP-Br</strong> demonstrates significant potential as a diagnostic and management tool for oxidative stress-related diseases, thereby advancing redox biology research and supporting the development of targeted therapeutic strategies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134750"},"PeriodicalIF":2.1,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144178737","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

Construction of an AIE-active fluorescent probe for rapid detection of ClO− in intracellular and extracellular microenvironments of live cells 构建aie活性荧光探针，快速检测活细胞胞内和胞外微环境中的氯离子

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-27 DOI: 10.1016/j.tet.2025.134753

Xiaozhua Qin , Yao Liu , Hang Wu , Chenlin Xu , Lu Wang , Xinchao Wang , Ge Ding

{"title":"Construction of an AIE-active fluorescent probe for rapid detection of ClO− in intracellular and extracellular microenvironments of live cells","authors":"Xiaozhua Qin , Yao Liu , Hang Wu , Chenlin Xu , Lu Wang , Xinchao Wang , Ge Ding","doi":"10.1016/j.tet.2025.134753","DOIUrl":"10.1016/j.tet.2025.134753","url":null,"abstract":"<div><div>Hypochlorite (ClO<sup>−</sup>) possesses properties of oxidation and plays an important role in defending against microbial attacks, thus, it is of great scientific and practical significance to develop a simple and convenient probe to recognize and detect ClO<sup>−</sup>. In this contribution, we have designed and constructed a tetraphenylethylene (TPE)-based AIE-active fluorescent probe <strong>TPEQ-ClO<sup>-</sup></strong> for rapid (within 100 s) and selective monitoring of ClO<sup>−</sup>, which contained a ClO<sup>−</sup> sensitive segment boronic ester, and in the presence of ClO<sup>−</sup>, the boronic ester group could be cut off and cause compound <strong>TPEQ</strong> formation, which turned on the AIE properties and realized dramatic enhancement in fluorescence intensity. Scanning electron microscopic (SEM) further demonstrated the AIE behavior of compound <strong>TPEQ,</strong> optical experiments confirmed that the probe possessed high selectivity, fast response time, and low detection limit (0.32 nM). In addition, <strong>TPEQ-ClO<sup>-</sup></strong> displayed good cell penetration and lower cytotoxicity, which created a available condition for the detection of ClO<sup>−</sup> inside and outside cells.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134753"},"PeriodicalIF":2.1,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144166462","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

Hydrogen-bond-induced Aza-Michael addition of imidazoles and quinones without additional base and DFT calculations 氢键诱导的咪唑和醌的Aza-Michael加成，无需额外的碱和DFT计算

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-27 DOI: 10.1016/j.tet.2025.134748

Wenjing Lu, Yongjun Zhang, Kun Bi, Zhirong Zhao, Xianqiang Huang, Guodong Shen

引用次数: 0

Visible-light mediated oxidative Diels-Alder reaction of hydroxylamines and 1,3-dienes 可见光介导的羟胺和1,3-二烯氧化Diels-Alder反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-27 DOI: 10.1016/j.tet.2025.134752

Meijun Zhu , Lanqin Liu , Yujie Zhi , Hong Hou

引用次数: 0

Photoinduced oxidation of benzylic hydrogens using N-bromosuccinimide 利用n -溴琥珀酰亚胺光诱导氧化苯基氢