Tetrahedron chem最新文献

Metal-free sulfenylation of pyrrolo[1,2-a]quinoxaline with diaryl disulfide facilitated by TBATB

Tetrahedron chem Pub Date : 2025-01-24 DOI: 10.1016/j.tchem.2025.100123

Yingqian Li, Yali Liu, Yan Liu, Xiaowei Ma, Liang Xu, Ping Liu

引用次数: 0

Synthesis of novel benzo fused bridged azaheterocycles through the reaction of chalcone with hydrazone 通过查尔酮与腙的反应合成新型苯并熔桥氮杂环

Tetrahedron chem Pub Date : 2025-01-23 DOI: 10.1016/j.tchem.2025.100122

Congyang Li , Ruochen Pang , Weiwu Ren

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Supramolecular light-harvesting systems based on cyanostilbene derivatives 基于氰芪衍生物的超分子光收集系统

Tetrahedron chem Pub Date : 2025-01-20 DOI: 10.1016/j.tchem.2025.100120

Fengyao Cui, Qiaona Zhang, Xiaoman Dang, Tangxin Xiao

{"title":"Supramolecular light-harvesting systems based on cyanostilbene derivatives","authors":"Fengyao Cui, Qiaona Zhang, Xiaoman Dang, Tangxin Xiao","doi":"10.1016/j.tchem.2025.100120","DOIUrl":"10.1016/j.tchem.2025.100120","url":null,"abstract":"<div><div>Photosynthesis provides a natural model for efficient light harvesting, inspiring the development of artificial systems designed to mimic this capability in capturing and converting solar energy. Artificial light-harvesting systems (LHSs) have thus become a key area of research, with promising applications in sensing, imaging, photocatalysis, and optoelectronics. Among the materials explored for LHSs, cyanostilbene derivatives stand out due to their ease of synthesis and unique photophysical properties, such as aggregation-induced emission (AIE) enhancement. These molecules can self-assemble into supramolecular structures through non-covalent interactions, including host–guest interactions, multiple hydrogen bonds, amphiphilic interactions, and metal-ligand coordination, offering tunable architectures for efficient energy transfer and light absorption. This minireview examines recent advancements in the design, synthesis, and functional performance of cyanostilbene-based supramolecular LHSs, analyzing their efficiency and adaptability in energy transfer processes. Future research may focus on integrating these systems with nanomaterials and exploring their potential in advanced energy conversion devices, offering new avenues for sustainable energy technologies.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100120"},"PeriodicalIF":0.0,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182681","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of Acylbenzo[b]thiophenes, benzofurans and indoles via intramolecular oxidative cyclization enabled by photocatalytic hydrogen atom transfer (HAT) 通过光催化氢原子转移 (HAT) 分子内氧化环化合成酰基苯并[b]噻吩、苯并呋喃和吲哚

Tetrahedron chem Pub Date : 2025-01-04 DOI: 10.1016/j.tchem.2025.100119

Fen-Dou Wang , Jin Jiang , Tiantian Xu , Wen-Chao Yang , Shu-Peng Zhang , Min Wang , Pinhua Li

引用次数: 0

A radical hydrohaloalkylation of the ligand sphere of a chiral dehydroalanine Ni(II) complex: An asymmetric route to halogenated α-amino acid derivatives 手性脱氢丙氨酸镍(II)配合物配体球的自由基氢烷基化：卤化α-氨基酸衍生物的不对称途径

Tetrahedron chem Pub Date : 2024-12-31 DOI: 10.1016/j.tchem.2024.100118

Nadezhda V. Stoletova , Alexander F. Smol'yakov , Andrey A. Tyutyunov , Victor I. Maleev , Vladimir A. Larionov

{"title":"A radical hydrohaloalkylation of the ligand sphere of a chiral dehydroalanine Ni(II) complex: An asymmetric route to halogenated α-amino acid derivatives","authors":"Nadezhda V. Stoletova , Alexander F. Smol'yakov , Andrey A. Tyutyunov , Victor I. Maleev , Vladimir A. Larionov","doi":"10.1016/j.tchem.2024.100118","DOIUrl":"10.1016/j.tchem.2024.100118","url":null,"abstract":"<div><div>An asymmetric synthetic protocol for the access to chiral artificial halogenated α-amino acid (α-AA) derivatives was elaborated through the radical functionalization of a double bond in the ligand sphere of a robust chiral dehydroalanine Belokon's Ni(II) complex by hydrohaloalkylation reaction. A 4-cyano-pyrydine/B<sub>2</sub>Pin<sub>2</sub> system promoted the <em>in situ</em> generation of radicals from halocarbons (including the hetero halogen atoms) for the subsequent coupling with the Ni(II) complex, providing the desired complexes with the yields in the range of 40–65%. The further post-modification of the side AA chain allowed to obtain the complexes with cyclopropane ring and to substitute the bromine atom on hydrogen one as well. Exemplary, two enantiopure α-AAs, including (<em>S</em>)-2-amino-4,4,4-trichlorobutanoic acid, were isolated by an acidic decomposition of the single diastereomeric Ni(II) complexes along with the recovery of the chiral auxiliary.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100118"},"PeriodicalIF":0.0,"publicationDate":"2024-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182240","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Design of a chiral molecular pocket in a Ni(II) complex to improve stereoselectivity in the kinetic resolution of racemic epoxides with CO2 Ni（II）配合物中手性分子袋的设计以提高外消旋环氧化合物与CO2的动力学拆分的立体选择性

Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100115

Mikhail A. Emelyanov , Alexander V. Bachinskiy , Yana V. Derkach , Vasiliy A. Chaliy , Alexander F. Smol'yakov , Michael G. Medvedev , Aleksei A. Titov , Victor I. Maleev , Vladimir A. Larionov

{"title":"Design of a chiral molecular pocket in a Ni(II) complex to improve stereoselectivity in the kinetic resolution of racemic epoxides with CO2","authors":"Mikhail A. Emelyanov , Alexander V. Bachinskiy , Yana V. Derkach , Vasiliy A. Chaliy , Alexander F. Smol'yakov , Michael G. Medvedev , Aleksei A. Titov , Victor I. Maleev , Vladimir A. Larionov","doi":"10.1016/j.tchem.2024.100115","DOIUrl":"10.1016/j.tchem.2024.100115","url":null,"abstract":"<div><div>The kinetic resolution of racemic epoxides using the carbon dioxide (CO<sub>2</sub>) molecule is of significant practical interest because the reaction yields the valuable products – enantiomerically enriched cyclic carbonates (1,3-dioxolan-2-ones), along with the remaining opposite enantiomer of the epoxide. However, one is the main challenges in this direction is the absence of the universal and efficient chiral catalytic systems for the resolution of different epoxides by CO<sub>2</sub> with a high selectivity factor (<em>s</em>). In this context, we herein present a perspective proof-of-concept approach for the improvement of stereoselectivity in the resolution of terminal epoxides by a rational design of an appropriate chiral molecular pocket in a Ni(II) complex based on commercially available (<em>S</em>)-(2-aminomethyl)pyrrolidine and 3,5-di-<em>tert</em>-butylsalicylaldehyde. The obtained chiral Ni(II) complex with iodide-anion catalyzes the kinetic resolution of epoxides by CO<sub>2</sub> with <em>s</em>-factor up to 7.8, while the addition of a suitable chiral ligand to this system, particularly, (<em>S</em>)-(2-anilinomethyl)pyrrolidine led to the increasing of <em>s</em>-factor up to 11.5 in the case of challenging styrene oxide (<em>ee</em> of styrene cyclic carbonate was 82%) which is being one of the best results for this substrate to date. It is gratifying to note that even achiral co-ligands can be used, greatly simplifying the catalytic system. The experimental and spectral data and DFT calculations revealed the mechanism of catalysis and enantioselection.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100115"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142757076","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Direct selective azidation of C(sp3)−H groups C(sp3)−H基团的直接选择性叠氮化反应

Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100114

Artem A. Antonov , Konstantin P. Bryliakov

引用次数: 0

Photo- and electro-chemical strategies for indazole synthesis

Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100116

Binbin Huang

引用次数: 0

Synthesis of allenones via nickel-catalyzed reductive coupling of propargyl esters with acyl chlorides

Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100113

Zhen Song, Yueming Wang, Ming Ma, Yuanhong Ma

引用次数: 0

Highly efficient and selective anticancer approach through acrolein-triggered cycloaddition chemistry in patient-derived xenografts: Mechanistic and preclinical investigation

Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100094

Yuria Takahashi , Kazuki Terashima , Taiji Shimoda , Masayuki Nagahashi , Koji Morimoto , Sayaka Urano , Kozo Kataoka , Hisashi Shinohara , Yasuo Miyoshi , Ambara R. Pradipta , Katsunori Tanaka

{"title":"Highly efficient and selective anticancer approach through acrolein-triggered cycloaddition chemistry in patient-derived xenografts: Mechanistic and preclinical investigation","authors":"Yuria Takahashi , Kazuki Terashima , Taiji Shimoda , Masayuki Nagahashi , Koji Morimoto , Sayaka Urano , Kozo Kataoka , Hisashi Shinohara , Yasuo Miyoshi , Ambara R. Pradipta , Katsunori Tanaka","doi":"10.1016/j.tchem.2024.100094","DOIUrl":"10.1016/j.tchem.2024.100094","url":null,"abstract":"<div><div>The efficacy of anticancer treatments in the clinical setting can be improved by decreasing off-target effects. Chemistry-based methods are emerging as a promising strategy to overcome this limitation. We previously developed a prodrug strategy using mitomycin C (MMC) activated at the tumor site by the [3 + 2] cycloaddition of endogenous acrolein, which is overexpressed in various cancers. Herein, we report the results of mechanistic and preclinical studies using a prodrug of doxorubicin (DOX), which is used in the treatment of several cancers, but its dosage is restricted by off-target effects. First, we developed robust chemistry methods for the synthesis of large amounts of prodrug for animal experiments. The DOX prodrug showed high anticancer efficacy without off-target effects even at high doses. Pharmacokinetic/pharmacodynamic, biodistribution, and serum protein binding studies supported the <em>in vivo</em> anticancer efficacy of DOX derivatization with the hydrophobic 2,6-diisopropyl azidobenzylcarbamate protecting group. This enhanced albumin binding, thereby increasing circulatory residence (serum stability). The stabilized prodrug could only be activated at the tumor site by reacting with endogenous acrolein to gradually release the required amounts of drug. Inhibiting overproduction of the drug and its circulation back into the blood minimized off-target effects. Nonspecific organ accumulation was not observed, supporting the safety of the prodrug <em>in vivo</em>. DOX and MMC prodrugs showed selective anticancer efficacy against patient-derived samples from lung, colorectal, gastric, and breast cancers. The proposed <em>in vivo</em> chemical strategy should be tested in clinical trials in the future.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100094"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129869","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0