Tetrahedron最新文献

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Design and synthesis of triphenylamine-based donor-acceptor systems with modulated acceptor strength for enhanced resistive WORM memory device applications 设计和合成基于三苯胺的调制受体强度供体-受体系统，用于增强电阻性WORM存储器件应用

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-16 DOI: 10.1016/j.tet.2025.135004

Valiya Parambath Megha , Madanan Akshaya , Predhanekar Mohamed Imran , Samuthira Nagarajan

A series of new Donor-Acceptor-based compounds was designed and synthesized with triphenylamine as the electron-donating unit, and 2-phenylbenzothiazole functionalized with 4-nitrophenyl, 4-cyanophenyl, 4-formylphenyl, and 4-trifluoromethylphenyl as acceptors. The photophysical studies reveal efficient intramolecular charge transfer, and the electrochemical analysis indicated irreversible oxidation with relatively lower optical band gaps ranging from 3.09 to 3.15 eV, supporting the compound's potential for effective charge transport. Thin-film morphology studies showed uniform surface coverage and high crystallinity, suggesting well-ordered molecular packing conducive to enhanced charge transport. All synthesized compounds were integrated into memory device architectures, exhibiting non-volatile binary Write-Once-Read-Many (WORM) behavior. The devices demonstrated excellent performance, with data retention stability exceeding 10³ s and an endurance capability of up to 100 programming cycles. Among the synthesized compounds, the compound containing the 4-formylphenyl group displayed the lowest switching threshold voltage and an ON/OFF current ratio of 10³, while the nitro-substituted compound showed the highest ON/OFF ratio of 10⁴, attributed to the strong electron-withdrawing nature of the nitro group. Computational studies supported the experimental findings, indicating that the memory-switching mechanism arises from a synergistic interaction of charge transfer and charge trapping processes.

以三苯胺为给电子基，以4-硝基苯基、4-氰苯基、4-甲酰苯基和4-三氟甲基苯基为受体功能化的2-苯基苯并噻唑为受体，设计合成了一系列新的供体-受体基化合物。光物理研究表明该化合物具有有效的分子内电荷转移，电化学分析表明该化合物具有不可逆氧化，具有相对较低的光学带隙（3.09 ~ 3.15 eV），支持该化合物具有有效电荷传输的潜力。薄膜形貌研究显示出均匀的表面覆盖和高结晶度，表明有序的分子堆积有利于增强电荷输运。所有合成的化合物都集成到存储设备架构中，表现出非易失性二进制写一次读多（WORM）行为。该器件表现出优异的性能，数据保持稳定性超过103秒，持久能力可达100个编程周期。在所合成的化合物中，含4-甲酰苯基的化合物的开关阈值电压最低，开/关电流比为103，而硝基取代的化合物的开/关比最高，为104，这是由于硝基的强吸电子性质。计算研究支持实验结果，表明记忆开关机制源于电荷转移和电荷捕获过程的协同相互作用。

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引用次数: 0

3-Ethylidene-6-dimethylaminoisoindolin-1-one formed via amine modification, a solvatochromic fluorophore for turn-on labeling with enhanced stability 通过胺修饰形成的3-乙基-6-二甲氨基异吲哚啉-1，一种用于开启标记的溶剂致变色荧光团，稳定性增强

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-16 DOI: 10.1016/j.tet.2025.135003

Yixuan Liu , Yukiko Abe-Sadamatsu , Chiyoe Ohta , Yang Pei , Mariko Aso

Proteins labeled with environment-sensitive fluorophores at specific sites can serve as powerful probes and sensors. We designed a 3-ethylidene derivative of 6-dimethylamino-methyleneisoindolin-1-one, a previously developed environment-sensitive fluorophore, which is generated via a reaction between lysine residues of target proteins and o-keto benzaldehyde derivatives bearing protein-binding ligands. However, the instability of the previously developed fluorophore under acidic conditions remained a concern. The introduction of an additional methyl group on the olefin enhanced the stability of the ethylidene fluorophore under acidic conditions (pH 6), relative to the methylene fluorophore, while retaining similar fluorescence properties. The formation of ethylidene fluorophore from an o-keto benzaldehyde derivative proceeded with similar efficiency to that of the methylene fluorophore in pH 7 buffer. The amine modification forming the stable ethylidene fluorophore developed in this study may be useful for our unique turn-on fluorescent protein modification at lysine residues using o-keto benzaldehyde derivatives.

在特定位置标记环境敏感荧光团的蛋白质可以作为强大的探针和传感器。我们设计了6-二甲氨基-亚甲基异吲哚啉-1- 1的3-乙基衍生物，该衍生物是由目标蛋白的赖氨酸残基与含有蛋白质结合配体的邻酮苯甲醛衍生物反应产生的。然而，先前开发的荧光团在酸性条件下的不稳定性仍然是一个问题。在烯烃上引入一个额外的甲基，增强了乙基荧光团在酸性条件下（pH值6）相对于亚甲基荧光团的稳定性，同时保持了类似的荧光性质。邻酮苯甲醛衍生物与亚甲基荧光团在pH为7的缓冲液中形成的效率相似。本研究开发的形成稳定的乙基荧光团的胺修饰可能有助于我们利用邻酮苯甲醛衍生物在赖氨酸残基上进行独特的荧光蛋白修饰。

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引用次数: 0

Visible-light-promoted deoxygenation reactions: A sustainable approach to green synthesis 可见光促进的脱氧反应：绿色合成的可持续途径

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-15 DOI: 10.1016/j.tet.2025.134982

Amal Tom Sebastian , Archana Vijayakumar , R. Bharath Krishna , M. Manod , Sudheesh T. Sivanandan , Chithra Mohan

Visible-light-enabled photoredox catalysis has emerged as a powerful tool in organic synthesis, revitalizing the field of radical chemistry. Deoxygenation reactions have always been integral to synthetic organic chemistry due to their unique versatility for the construction of diverse molecular architectures. With the growing need for sustainability in synthetic protocols, green strategies for radical generation in deoxygenative processes have become essential. In this regard, visible-light-enabled deoxygenation strategies have garnered significant attention, offering efficient access to valuable molecular scaffolds under mild conditions. These methods often exhibit high selectivity and excellent functional group tolerance. This review highlights recent advancements in both photocatalytic systems and catalyst-free approaches for deoxyfunctionalization reactions for the formation of carbon-carbon and carbon-heteroatom bonds.

可见光激活的光氧化还原催化已成为有机合成的有力工具，使自由基化学领域重新焕发活力。脱氧反应一直是有机合成化学中不可或缺的一部分，因为它具有独特的多功能性，可以构建不同的分子结构。随着合成工艺对可持续性的需求日益增长，在脱氧过程中产生自由基的绿色策略变得至关重要。在这方面，可见光激活脱氧策略已经引起了极大的关注，提供了在温和条件下有效获取有价值的分子支架的途径。这些方法通常具有高选择性和优异的官能团耐受性。本文综述了光催化系统和无催化剂方法在碳-碳和碳杂原子键形成的脱氧官能化反应中的最新进展。

引用次数: 0

Applying molecular hybridization to design a new class of cinnolino[3,4-a]carbazoles as potential anticancer agents 应用分子杂交技术设计一类新的肉桂酸[3,4-a]咔唑作为潜在的抗癌药物

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-15 DOI: 10.1016/j.tet.2025.134990

Lian Li , Lu Liu , Baichen He , Juan Luo , Lina Bai , Zhili Zhang , Qiang Tang

In this study, a series of cinnolino[3,4-a]carbazole compounds were synthesized in excellent yields through a simple and efficient diazotization reaction of 2-(2-aminophenyl)carbazole. To evaluate their in vitro anticancer potential, the antiproliferative activity of these compounds was assessed against four cancer cell lines: HepG2 (hepatocellular carcinoma), NCI–H1688 (lung cancer), HT29 (colon cancer), and 143B (osteosarcoma). Among the tested compounds, 6b exhibited the most potent inhibitory activity against HT29 colon cancer cells, with an IC₅₀ value of 2.089 μmol/L, while 6f showed the strongest inhibitory effect on the proliferation of 143B osteosarcoma cells, with an IC₅₀ of 2.056 μmol/L. These in vitro anticancer activity assay results indicate that cinnolino[3,4-a]carbazole compounds hold promise for further development as potential anticancer therapeutic agents.

本研究通过简单高效的2-（2-氨基苯基）咔唑重氮化反应，以优异的收率合成了一系列cinnolino[3,4-a]咔唑类化合物。为了评估其体外抗癌潜力，我们评估了这些化合物对四种癌细胞系的抗增殖活性：HepG2（肝细胞癌）、NCI-H1688（肺癌）、HT29（结肠癌）和143B（骨肉瘤）。其中6b对HT29结肠癌细胞的抑制作用最强，IC50值为2.089 μmol/L； 6f对143B骨肉瘤细胞的增殖抑制作用最强，IC50值为2.056 μmol/L。这些体外抗癌活性分析结果表明，cinnolino[3,4-a]咔唑类化合物有望作为潜在的抗癌药物进一步开发。

引用次数: 0

Asymmetric Michael addition of glycine-derived schiff bases to azadienes catalyzed by a quinidine-derived chiral catalyst 奎尼丁衍生的手性催化剂催化甘氨酸衍生的希夫碱对氮二烯的不对称Michael加成反应

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-14 DOI: 10.1016/j.tet.2025.134991

Yue Liu, Jie Liu, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan

A highly enantioselective Michael addition reaction between azadienes and glycine Schiff bases catalyzed by a quinidine-derived chiral phase-transfer catalyst have been developed. Employing this strategy, a series of chiral amino acid derivatives featuring benzofuran scaffolds with adjacent stereocenters were efficiently synthesized in high yields (up to 99 %), with excellent diastereoselectivity (up to 97:3 dr) and enantioselectivity (up to 96 % ee).

在奎尼丁衍生的手性相转移催化剂催化下，偶氮二烯与甘氨酸席夫碱发生了高度对映选择性的Michael加成反应。利用这一策略，以邻体中心苯并呋喃为支架的一系列手性氨基酸衍生物以高收率（高达99%）高效合成，具有优异的非对映选择性（高达97:3 dr）和对映选择性（高达96% ee）。

引用次数: 0

Synthesis of cyclopropyl carbocyclic nucleoside analogues via reductive cyclopropanation of N-allylheteroaromatics with dimethyl 2-oxomalonate n -烯丙基杂芳烃与2-羟丙酸二甲酯还原环丙化合成环丙基碳环核苷类似物

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-13 DOI: 10.1016/j.tet.2025.134992

Ke-Xin Huang , Feng-Yi Lai , Ke-Xin Zhang , Cai-Jing Li , Zhao-Yang Chen , Wen-Chao Gao

An innovative and highly efficient synthetic methodology has been developed for the preparation of nucleoside analogues featuring a cyclopropane-methylene-nucleobase scaffold. It involves N-allylheteroaromatic substrates reacting with dimethyl 2-oxomalonate in a P(NMe₂)₃-mediated deoxygenation process, yielding the products in high yields (21 examples, up to 92 % yield). This reaction features the use of safer and more accessible feedstocks, metal-free catalysis, and a broad substrate scope, demonstrating significant potential for practical application in nucleoside chemistry.

一种创新和高效的合成方法已经开发用于核苷类似物的制备具有环丙烷-亚甲基-核碱基支架。它涉及n -烯丙基杂芳香底物在P(NMe2)3介导的脱氧过程中与2-氧丙二酸二甲酯反应，产生高收率的产品（21个例子，高达92%收率）。该反应的特点是使用更安全、更容易获得的原料、无金属催化和广泛的底物范围，在核苷化学中显示出巨大的实际应用潜力。

引用次数: 0

Iodobenzene diacetate mediated o-phenylenediamines oxidative radical annulation toward phenazines: direct access to phenazine-1-carboxylic acid and phenazine-1-carboxamide 二醋酸碘介导的邻苯二胺对非那嗪的氧化自由基环化：直接接触非那嗪-1-羧酸和非那嗪-1-羧酰胺

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-12 DOI: 10.1016/j.tet.2025.134996

Jianwei Yan, Jiangfei Wang, Jing Yuan, Jiaxin Lu, Yiwan Jiang, Xiaobing Li, Tianjun Ni

A novel expeditious approach to phenazines via iodobenzene diacetate mediated oxidative annulation of o-phenylenediamines with catechols was developed. The transformation proceeds under mild conditions and can be completed within 3 min with a broad raw materials substrate scope. This methodology not only allows for the rapid synthesis of a wide variety of phenazines but also efficiently produces valuable phenazines metabolites, such as phenazine-1-carboxylic acid (PCA) and phena-zine-1-carboxamide (PCN), in a single step. The gram-scale result of this reaction highlights its practical utility. Experimental studies support a radical cascade mechanism.

提出了一种通过二醋酸碘介导邻苯二胺与儿茶酚氧化环反应快速合成苯那嗪的新方法。转化在温和的条件下进行，可在3分钟内完成，原料基材范围广。该方法不仅可以快速合成多种非那嗪，而且可以在一个步骤中有效地产生有价值的非那嗪代谢物，如非那嗪-1-羧酸（PCA）和非那嗪-1-羧酰胺（PCN）。该反应的克级结果突出了它的实用性。实验研究支持自由基级联机制。

引用次数: 0

Highly practical synthesis of propranolol and esmolol via epoxide ring-opening 环氧化开环法合成普萘洛尔和艾司洛尔

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-11 DOI: 10.1016/j.tet.2025.134995

Jing Zhao , Li Li , Dong Li , Shibo Yu , Silei Ye , Jing Wang , Xiao Long Liu , Guo-lan Ma , Jing-bo Chen

Conventionally, the synthesis of propranolol and esmolol often rely on metal catalysts or/and environmentally hazardous solvents. Building upon our pioneering metal-free catalytic approach, this study achieves the highly efficient and sustainable synthesis of propranolol and esmolol through an acetic acid-mediated epoxide ring-opening reaction coupled with an alcohol additive strategy. The developed method demonstrates excellent operational simplicity while eliminating the requirement for transition metal catalysts, providing an environmentally benign alternative for the synthesis of β-blocker pharmaceuticals.

传统上，心得安和艾司洛尔的合成通常依赖于金属催化剂或/和对环境有害的溶剂。在我们开创性的无金属催化方法的基础上，本研究通过乙酸介导的环氧化物开环反应以及酒精添加剂策略，实现了高效和可持续的心得洛尔和艾司洛尔合成。该方法操作简单，不需要过渡金属催化剂，为合成β阻断剂药物提供了一种环境友好的替代方法。

引用次数: 0

Synthesis of 4-aryl tetrahydropyrans from epoxides and allyltrimethylsilane 环氧化物与烯丙基三甲基硅烷合成4-芳基四氢吡喃

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-11 DOI: 10.1016/j.tet.2025.134994

A.M. Borude , A.P. Thorat , P.A. Nagwade , G.G. Muley , A.B. Gambhire

The synthesis of 4-aryltetrahydropyrans utilizing epoxides and allyltrimethylsilanes in combination with arenes under Prins cyclization conditions, achieving moderate to good yields.

以环氧化物、烯丙基三甲基硅烷和芳烃为原料，在普林斯环化条件下合成4-芳基四氢吡喃，收率中高。

引用次数: 0

Richernoids A‒D, 20-nor-ent-podocarpane diterpenoids with antibacterial activity from Richeriella gracilis 薄叶richheriella gracilis中具有抗菌活性的类richheroid A-D， 20-no -对-podocarpane二萜

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-10-11 DOI: 10.1016/j.tet.2025.134993

Jin-Qiu You , Chun-Yang Zhang , Jin-Yi Cao , Xing-Xin Jiang , Xiang-Yun Peng , Wei-Zhen Huang

The phytochemical investigation on the ethanol extract of Richeriella gracilis afforded four undescribed 20-nor-ent-podocarpane diterpenoids richernoids A‒D (1–4), together with three known analogues (5–7). Structures of these compounds were fully established using combined methods, including 1D and 2D NMR, HRESIMS, electronic circular dichroism (ECD) analysis, and single-crystal X-ray diffraction. Compounds 1–4 belong to the class of ent-podocarpane skeleton featuring a rare γ-butyrolactone moiety. Compounds 1 and 2 exhibited moderate inhibitory activities against Helicobacter pylori (ATCC 43504 and Hp-SS1) with MIC values of 16–64 μg/mL.

对薄叶richheriella gracilis乙醇提取物进行了植物化学研究，得到了四种未描述的20-no -ent-podocarpane二萜richernoids A-D(1-4)，以及三种已知的类似物（5-7）。通过1D和2D NMR、hresms、电子圆二色性（ECD）分析和单晶x射线衍射等综合方法，完全确定了这些化合物的结构。化合物1-4属于含有稀有γ-丁内酯片段的对-聚碳烷骨架类。化合物1和2对幽门螺杆菌（ATCC 43504和Hp-SS1）具有中等抑制活性，MIC值为16 ~ 64 μg/mL。

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