Tetrahedron最新文献_第9页

Synergistic Pd(OAc)2/CuI-catalyzed alkynylation of β-lactam derivative via Sonogashira coupling Pd(OAc)2/CuI 催化的通过 Sonogashira 偶联的 β-内酰胺衍生物的协同炔化反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-03 DOI: 10.1016/j.tet.2024.134290

Rachana Upadhyay, Amit B. Patel

{"title":"Synergistic Pd(OAc)2/CuI-catalyzed alkynylation of β-lactam derivative via Sonogashira coupling","authors":"Rachana Upadhyay, Amit B. Patel","doi":"10.1016/j.tet.2024.134290","DOIUrl":"10.1016/j.tet.2024.134290","url":null,"abstract":"<div><div>Herein, a novel approach of bimetallic Pd(OAc)<sub>2</sub>/CuI-catalyzed alkynylation of 3-chloroazetidin-2-one (<em>β</em>-lactam derivative) with terminal alkyne <em>via</em> tandem C–C bond activation/Sonogashira-type cross-coupling reaction is developed. This synthesis encompasses a sequence of inert Csp<sup>3</sup>–X/Csp–H functionalization processes involving the coupling of the C(sp<sup>3</sup>) adjacent to the 3-chloroazetidin-2-one with the C(sp) of a terminal alkyne. The final analogs are synthesized by means of the indole-benzothiazole Schiff base formation, cyclization of the Schiff base to generate the <em>β</em>-lactam derivative, and Sonogashira coupling to afford a C(sp<sup>3</sup>)–C(sp) bond. In addition, indole, benzothiazole, and azetidine-2-one have been identified to be highly efficient heterocyclic scaffolds with a range of pharmacological benefits. It encouraged us to discover a hybrid compound that had each of these moieties. Cooperation between two different metals is essential for the successful implementation of this approach. Specifically, the interaction between the Pd and Cu centers in the transmetallation step is depicted through a plausible mechanistic route. The reaction conditions have been optimized by varying catalyst and ligand loadings, bases, temperatures, and solvents. The reaction is highly efficient, yielding alkynylated products in up to 84 % yield with a wide range of substrates and functional group tolerance, thereby serving as a functional model for the Sonogashira coupling reaction.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134290"},"PeriodicalIF":2.1,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425566","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

A helical salicylaldehyde Schiff base exhibiting aggregation-induced emission and selective recognition of Cu2+ ions 一种螺旋状水杨醛席夫碱，具有聚集诱导发射和选择性识别 Cu2+ 离子的特性

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-02 DOI: 10.1016/j.tet.2024.134288

Mao-Juan Tian, Hua-Qing Tian, Tao Jiang, Huan-Huan Yu, Chao Huang, Bi-Xue Zhu, Chun Zhu

{"title":"A helical salicylaldehyde Schiff base exhibiting aggregation-induced emission and selective recognition of Cu2+ ions","authors":"Mao-Juan Tian, Hua-Qing Tian, Tao Jiang, Huan-Huan Yu, Chao Huang, Bi-Xue Zhu, Chun Zhu","doi":"10.1016/j.tet.2024.134288","DOIUrl":"10.1016/j.tet.2024.134288","url":null,"abstract":"<div><div>A racemic salicylaldehyde Schiff base (<strong>L</strong>) containing a pyridine-2,6-dicarboxamide scaffold was successfully synthesized and characterized. <strong>L</strong> exhibited a typical aggregation-induced emission (AIE) characteristic in the mixed solvent of THF/H<sub>2</sub>O. The UV–Vis absorption spectra and fluorescence emission spectra showed a high selectivity and sensitivity of <strong>L</strong> for the recognition of Cu<sup>2+</sup> over other ions in the solution of THF/H<sub>2</sub>O (2:3), and indicated <strong>L</strong> can be used as a turn-off fluorescent probe for Cu<sup>2+</sup>. The stoichiometric ratio, association constant, and the detection limit of probe <strong>L</strong> toward Cu<sup>2+</sup> were estimated using Job's plot method, UV–Vis spectra titration, and fluorescence spectra titration. More importantly, a Cu(II) complex was synthesized from the coordination interaction of probe <strong>L</strong> with Cu<sup>2+</sup> and characterized by X-ray crystal diffraction technique. The crystal structure well illustrated the binding mode of <strong>L</strong> with Cu<sup>2+</sup>, contributing to the further understanding of the coordination mechanism.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134288"},"PeriodicalIF":2.1,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425568","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

I2-promoted direct C–H arylselenylation of pyrrolo[1,2-a]quinoxalines I2 促进的吡咯并[1,2-a]喹喔啉的直接 C-H 芳基硒化反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-30 DOI: 10.1016/j.tet.2024.134287

Di Hao , Zhen Yang , Luigi Vaccaro , Ping Liu , Bin Dai

引用次数: 0

An acid-mediated synthesis of substituted naphthalenes from ortho-alkynyl tertiary benzylic alcohols 酸介导的邻炔基三级苄醇合成取代萘的方法

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-29 DOI: 10.1016/j.tet.2024.134285

Puja Singh, Sreenivasulu Chinnabattigalla, Komal Goel, Ravi Kishore Dakoju, Satyanarayana Gedu

引用次数: 0

Synthesis of exocyclic enaminone-based thiohydantoins as potent antifungal agents 合成外环烯酮基硫代氢蒽作为强效抗真菌剂

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-29 DOI: 10.1016/j.tet.2024.134286

Ulises F. Reyes-González , Edson Barrera , Daniela Martínez-López , R. Israel Hernández-Benitez , Julio López , Omar Gómez-García , Dulce Andrade-Pavón , Lourdes Villa-Tanaca , Paola Castillo-Juárez , Francisco Delgado , Joaquín Tamariz

引用次数: 0

1,2,3-Triazole nilotinib analogues: Synthesis and Cytotoxic activity 1,2,3-三唑尼洛替尼类似物：合成与细胞毒性活性

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-26 DOI: 10.1016/j.tet.2024.134284

Leticia Almazán-Sánchez , María Teresa Ramírez-Apan , David Morales-Morales , Marco A. García-Eleno , Erick Cuevas-Yañez

引用次数: 0

Synthesis and BSA binding study of the Cu(II) complex and applications of it to enhance catalytic activity for C(Sp2)-H bond functionalization and for the synthesis of polyhydroquinolines Cu(II) 复合物的合成和 BSA 结合研究及其在提高 C(Sp2)-H 键官能化催化活性和合成多氢喹啉中的应用

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-25 DOI: 10.1016/j.tet.2024.134278

Aminul Islam , Kakoli Malakar , Marappan Velusamy , Pranab Ghosh

{"title":"Synthesis and BSA binding study of the Cu(II) complex and applications of it to enhance catalytic activity for C(Sp2)-H bond functionalization and for the synthesis of polyhydroquinolines","authors":"Aminul Islam , Kakoli Malakar , Marappan Velusamy , Pranab Ghosh","doi":"10.1016/j.tet.2024.134278","DOIUrl":"10.1016/j.tet.2024.134278","url":null,"abstract":"<div><div>Among the various copper-catalyzed coupling reactions, <em>C</em>–S and <em>C</em>–N bond-forming reactions have carried off plentiful recognition due to their demand in the synthesis of molecules having biological and pharmaceutical impact. Organo-copper complex has an incontestable supremacy over the other catalytic complex due to its low cost and the use of readily accessible and stable ligands. As a consequence and in continuation of our explorative studies in this direction, an efficient and novel organo-copper complex has been synthesized and characterized by spectroscopic (NMR, FT-IR) and single crystal X-ray diffraction (XRD) methods. The synthesized stable metal complex has fascinating physical, chemical, biological and catalytic properties. In the chemical exploration refer to protein-metal interactions; we have often used Bovine Serum Albumin (BSA) protein. The synthesized copper complex has the potential to form coordinate bonds with functional groups present in BSA, together with amino acid residues and the protein backbone. The binding of metal complexes to BSA has outstanding imputation in medicinal chemistry. For enhancement of the catalytic activity of the organo-copper complex, we have evaluated it in carbon-hetero bond formation reactions where it proffered an influential tool for the establishment of <em>C</em>–S and <em>C</em>–N bonds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134278"},"PeriodicalIF":2.1,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425567","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

Facile synthesis of 2-substituted benzofurans by intermolecular [3+2] cycloaddition of benzoquinone and vinyl azides under air 在空气中通过苯醌和乙烯基叠氮化物的分子间 [3+2] 环加成法简便合成 2-取代的苯并呋喃

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-21 DOI: 10.1016/j.tet.2024.134277

Pengfei Sun , Xin Yu , Fang Wei

引用次数: 0

Trichoglutamides A to C from yellow Tricholoma species 来自黄色毛喉类的毛喉酰胺 A 至 C

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-20 DOI: 10.1016/j.tet.2024.134276

Yumiko Oba , Yuri Nakamura , Mitsuru Kondo , Jing Wu , Makoto Urai , Motohiro Tomizawa , Hirokazu Kawagishi , Kimiko Hashimoto

引用次数: 0

DMSO suppresses duclauxin biosynthetic pathway in Talaromyces sp. (strain IQ-313) and untaps terpenoids, polyketides and meroterpenoids biosynthesis DMSO 可抑制 Talaromyces sp.（菌株 IQ-313）的杜仲苷生物合成途径，并解除萜类化合物、多酮类化合物和经萜类化合物的生物合成过程

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-20 DOI: 10.1016/j.tet.2024.134283

Enrique Aguilar-Ramírez, José Rivera-Chávez, Valeria Abogado-Aponte, Beatriz Quiroz-García, Adriana Romo-Pérez

{"title":"DMSO suppresses duclauxin biosynthetic pathway in Talaromyces sp. (strain IQ-313) and untaps terpenoids, polyketides and meroterpenoids biosynthesis","authors":"Enrique Aguilar-Ramírez, José Rivera-Chávez, Valeria Abogado-Aponte, Beatriz Quiroz-García, Adriana Romo-Pérez","doi":"10.1016/j.tet.2024.134283","DOIUrl":"10.1016/j.tet.2024.134283","url":null,"abstract":"<div><div><em>Talaromyces</em> sp. (strain IQ-313) produces duclauxin-type molecules under standard fermentation conditions in rice and oat cereal. Such molecules are of great interest due to their structural complexity and biological activity. Interestingly, application of an OSMAC (<em>One Strain Many Compounds</em>) approach, revealed that the biosynthetic machinery of this fungus can be directed towards the production of other types of molecules, while completely suppressing the biosynthesis of duclauxin (<strong>1</strong>). To exploit the metabolic potential of <em>Talaromyces</em> sp. (strain IQ-313), it was grown on solid media supplemented with dimethyl sulfoxide (DMSO), an ectopic epigenetic modulator. Metabolomic analysis of the fermentation extract from the strain grown under standard and DMSO-supplemented conditions, using molecular networking, revealed notable differences in the profiles. Chemical investigation of the extract obtained under abiotic stress led to the isolation and characterization of 15 molecules not detected under standard conditions, including nine polyketides, one sesquiterpenoid, two sesterterpenoids, and three meroterpenoids. Among these, talaromophilane (<strong>2</strong>), an eremophilane sesquiterpenoid, and talaroisochromane (<strong>8</strong>), an oxoisochromen, have not been previously reported in the literature. The structures of all isolates were established using a combination of spectroscopic and spectrometric data. The absolute configuration of compound <strong>2</strong> was established based on the analysis of NOESY interactions and by comparison of the experimental and theoretical electronic circular dichroism (ECD) curves.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134283"},"PeriodicalIF":2.1,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0040402024004642/pdfft?md5=f41bf2a92a1c3589c2cb0c13de276092&pid=1-s2.0-S0040402024004642-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142310472","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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