Tetrahedron最新文献

英文中文

A smartphone-assisted chromogenic and fluorogenic dual-channel sensor for specific determination of toxic Pb2+ ions with multifaceted applications 用于特异性测定有毒 Pb2+ 离子的智能手机辅助显色和荧光双通道传感器的多方面应用

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-21 DOI: 10.1016/j.tet.2024.134316

Haiyan Xu , Wenlong Qin , Junyu Zhu , Ying-Guo Liu

Heavy metal pollutants, such as Pb²⁺ ions, pose a substantial hazard to human health and ecosystems, and it was of great significance to develop cost-effective and portable techniques for online and visual detection of Pb²⁺. Herein, we fabricated a novel chromogenic and fluorogenic dual-channel sensor NQA through a Schiff base reaction involving a dicyanoisophorone derivative and isoniazid, enabling effective detection of Pb²⁺ ions. Upon complexation with Pb²⁺ ions at a 1:1 M ratio, the fluorescence intensity of NQA exhibited a remarkable enhancement. The naked-eye colorimetric detection utilizing NQA demonstrated a distinct color change to specific Pb²⁺ ions concentration from yellow to light pink. Based on this principle, a smartphone-assisted sensing platform was developed for visual and high-quality identification of Pb²⁺ in real samples. The UV binding constant for Pb²⁺ ions was determined to be 1.84 × 10⁵ M⁻¹, with a detection limit of 0.38 μM. Furthermore, the versatility of NQA extended to applications in naked-eye test paper experiments, the detection of Pb²⁺ ions in real water samples and living cells, showcasing its potential for environmental and biological monitoring.

以 Pb2+ 离子为代表的重金属污染物对人类健康和生态系统造成了严重危害，因此开发经济、便携的 Pb2+ 在线可视检测技术具有重要意义。在此，我们通过二氰异佛尔酮衍生物与异烟肼的希夫碱反应，制备了一种新型发色性和发荧光性双通道传感器 NQA，从而实现了对 Pb2+ 离子的有效检测。以 1:1 M 的比例与 Pb2+ 离子络合后，NQA 的荧光强度显著增强。利用 NQA 进行的肉眼比色检测显示，特定的 Pb2+ 离子浓度会产生从黄色到浅粉色的明显颜色变化。基于这一原理，我们开发了一种智能手机辅助传感平台，用于对实际样品中的 Pb2+ 进行高质量的肉眼识别。经测定，Pb2+ 离子的紫外结合常数为 1.84 × 105 M-1，检测限为 0.38 μM。此外，NQA 的多功能性还扩展到了裸眼试纸实验、真实水样和活细胞中 Pb2+ 离子的检测等方面的应用，展示了其在环境和生物监测方面的潜力。

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引用次数: 0

Electro-promoted radical-radical cross-coupling reaction to synthesize sulfonamides 电促进自由基-自由基交叉偶联反应合成磺胺类药物

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-20 DOI: 10.1016/j.tet.2024.134315

Hang Gong , Hongmei Fu , Chao Lu , Changqun Cai

An electrochemical decarbonylation of DMF to achieve N,N-dimethyl amino radical and denitrification of sulfonyl hydrazide to achieve sulfonyl radical in the absence of transition metal and additional oxidant was reported here. Signifyingly, cross-coupling reaction rather than homocoupling reactions completely prevail in competition to obtain sulfonamides, which usually exist as skeletons of pharmaceuticals. This work provides a new method for cracking DMF into N,N-dimethylamino radical, and found a value-added application of this industrialized bulk chemical to the synthesis of sulfonamides.

本文报告了在没有过渡金属和额外氧化剂的情况下，通过电化学方法对 DMF 进行脱羰基反应以获得 N,N-二甲基氨基自由基，并对磺酰肼进行脱硝反应以获得磺酰基自由基。值得注意的是，在获得磺酰胺的竞争中，交叉偶联反应比均偶联反应完全占优势，而磺酰胺通常作为药物的骨架存在。这项工作提供了一种将 DMF 裂解为 N,N-二甲基氨基自由基的新方法，并发现了这种工业化大宗化学品在合成磺酰胺类化合物中的增值应用。

引用次数: 0

Steroid-based hydrazones as anabolic agents: Design, synthesis, computational studies, and biological evaluation in human skeletal muscle cell line 作为同化制剂的类固醇酰肼：设计、合成、计算研究以及在人类骨骼肌细胞系中的生物学评估

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-19 DOI: 10.1016/j.tet.2024.134305

Fermín Flores-Manuel , Gabriel Guerrero-Luna , Israel Quiroga-Montes , Kenia Salvador-Atonal , Amairani Domínguez-Bahena , Maura Cárdenas-García , María Guadalupe Hernández-Linares

Hydrazone derivatives were synthesized in a three-step process starting from diosgenin and then tested for their anabolic activity. Through in silico analysis, we identified proteins associated with muscle growth to elucidate the plausible mechanisms and interactions between these compounds and the active site amino acids, thereby providing a rationale for the observed biological results. The results of the in vitro assay on the human skeletal muscle cell line showed an increase in the number of viable cells, which was determined using increasing concentrations of each compound through the XTT assay. Additionally, the increase in protein concentration was measured using the Bradford method. The experimental evaluation revealed that all compounds have differences in increased protein/cell percentage compared to the control and testosterone, which suggests a hyperplastic/hypertrophic effect with a normal morphology.

我们通过三步法合成了腙的衍生物，并测试了它们的合成代谢活性。我们通过硅学分析确定了与肌肉生长相关的蛋白质，以阐明这些化合物与活性位点氨基酸之间的合理机制和相互作用，从而为观察到的生物学结果提供理论依据。对人类骨骼肌细胞系进行的体外试验结果表明，通过 XTT 试验，使用浓度不断增加的每种化合物，可存活的细胞数量有所增加。此外，还使用布拉德福德法测量了蛋白质浓度的增加。实验评估结果表明，与对照组和睾酮相比，所有化合物在增加蛋白质/细胞百分比方面都存在差异，这表明这些化合物具有增生/肥大作用，形态正常。

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引用次数: 0

Transition metal-catalyzed olefination of alkyl heteroarenes with alcohols 过渡金属催化烷基杂环戊烯与醇的烯化反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-18 DOI: 10.1016/j.tet.2024.134306

Bin Guo , Jing Zhang , Dan Chen , David J. Young , Hong-Xi Li

Transition metal catalyzed direct olefination of alkyl heteroarenes with alcohols using acceptorless dehydrogenative coupling (ADC) reactions and aerobic oxidative olefination are effective, versatile transformations for the construction of alkenyl heterocyclic compounds. Various transition metal catalysts based on noble metals (Ru) and their earth-abundant equivalents (Mn, Ni, Fe, Co) have been employed for these protocols. Water and hydrogen are the only byproducts and the starting alcohols are less toxic, more readily available, more easily handled and more atom economical than their halogen counterparts. This review details recent advances in these green methodologies, describing scope, reaction mechanisms, chemo-selectivity and applications in synthesis.

利用无受体脱氢偶联（ADC）反应和有氧氧化烯烃化反应，过渡金属催化烷基杂环与醇的直接烯烃化反应，是构建烯基杂环化合物的有效、多用途转化方法。在这些方案中使用了各种基于贵金属（Ru）及其富土等价物（Mn、Ni、Fe、Co）的过渡金属催化剂。水和氢是唯一的副产品，而起始醇与卤素对应物相比，毒性更小、更容易获得、更易于处理、原子更经济。本综述详细介绍了这些绿色方法的最新进展，包括范围、反应机理、化学选择性以及在合成中的应用。

引用次数: 0

1,5-Disubstituted-1,2,3-Triazoles as GABA analogues: Synthesis, QSAR and biological evaluation as Pseudomonas fluorescens GABA-AT inhibitors 作为 GABA 类似物的 1,5-二取代-1,2,3-三唑：作为荧光假单胞菌 GABA-AT 抑制剂的合成、QSAR 和生物学评价

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-18 DOI: 10.1016/j.tet.2024.134300

Lucero Díaz-Peralta , Mario Fernandez-Zertuche , Juan Alberto Guevara-Salazar , Jessica R. Moran-Diaz , Luis Eduardo Hernandez-Dominguez , Rodrigo Said Razo-Hernández

We report the synthesis of a new series of γ-aminobutyric acid (GABA) analogues as possible GABA-AT inhibitors, where the nitrogen at the Ƴ-position is contained in a 1,5-disubstituted-1,2,3-triazole ring system. The triazole ring system was assembled by the Ru(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (RuACC) protocol. GABA-AT inhibition activity was predicted by means of a QSAR model that was constructed in this work. Different molecular descriptors families were employed for its construction, like steric type (

W a p

and

P W 5

), solubility type (

Δ PSA

), and electronic type (

Δ {T r i a z o l e}_{3}

). Additionally, a similarity analysis based on the electronic profile of 1,5-triazole and 1,4-triazole GABA analogues was done to support the QSAR predictions. Finally, the three best candidates were biologically tested as Pseudomonas fluorescens GABA-AT inhibitors showing an inhibition percent compared to FDA approved inhibitors.

我们报告了一系列新的γ-氨基丁酸（GABA）类似物的合成，这些类似物可能是 GABA-AT 抑制剂，其中位于Ƴ位的氮包含在一个 1,5 二甲基-1,2,3-三唑环体系中。该三唑环系统是通过 Ru(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (RuACC) 方案组装而成的。本研究通过构建 QSAR 模型预测了 GABA-AT 抑制活性。该模型的构建采用了不同的分子描述符系列，如立体类型（Wap 和 PW5）、溶解类型（ΔPSA）和电子类型（ΔTriazole3）。此外，还根据 1,5-三唑和 1,4- 三唑 GABA 类似物的电子特征进行了相似性分析，以支持 QSAR 预测。最后，这三种最佳候选化合物作为荧光假单胞菌 GABA-AT 抑制剂进行了生物测试，结果显示其抑制率与美国食品及药物管理局批准的抑制剂相当。

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引用次数: 0

Assembling phthalaldehyde and o-aminochalcones by Pd(II) catalyzed tandem reaction for synthesizing isoindoloindonole fluorophores 通过钯(II)催化串联反应组装邻苯二甲醛和邻氨基查耳酮以合成异吲哚吲哚荧光团

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-11 DOI: 10.1016/j.tet.2024.134302

Arunava Misra, Mohabul Alam Mondal

One-pot synthesis of isoindoloindonoles having various auxochrome, from easily available starting materials phthalaldehyde and o-aminochalcone, involving palladium(II) acetate catalysis in acetic acid is reported. A mechanism based on the formation of 2-aryl-2H-isoindol-1-ol (22) intermediate is proposed for the formation of the tetracyclic core of isoindoloindonoles. The possible intramolecular cyclization via the direct participation of the carbonyl vs the adjacent αβ-conjugated double bond was evaluated. Thus, a detailed study on how the presence of electronically different groups at the β position of chalcones affects the outcome of the cyclization reaction and the photophysical properties of the resulting isoindoloindolones is presented here. Furthermore, the core structure was determined using NMR, mass and single-crystal X-ray diffraction analysis.

本研究报道了在乙酸中通过乙酸钯（II）催化，从易于获得的起始原料邻苯二甲醛和邻氨基查尔酮出发，一步法合成具有各种辅助色素的异吲哚吲哚类化合物。提出了一种基于 2-芳基-2H-异吲哚-1-醇 (22) 中间体形成的机制，用于形成异吲哚酮类化合物的四环核心。通过羰基与邻近的 αβ 共轭双键的直接参与，对分子内环化的可能性进行了评估。因此，本文详细研究了在查耳酮的 β 位上存在电子不同的基团如何影响环化反应的结果以及所得异吲哚吲哚酮的光物理特性。此外，还利用核磁共振、质量和单晶 X 射线衍射分析确定了核心结构。

引用次数: 0

Visible-light-mediated cyclopropanation reactions of 3-diazooxindoles with olefins 可见光介导的 3-重氮氧化吲哚与烯烃的环丙烷化反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-11 DOI: 10.1016/j.tet.2024.134296

Zhuangzhuang Mu, Haochi Xie, Shundong Gan, Hujin Li, Yanan Hou, Mingcheng Qian, Shuai Zhao, Xin Chen

Visible-light-mediated metal-free cyclopropanation reaction of diazo compounds with different olefins or arenes have been fully developed in recent years. However, electron-deficient olefins still could not be well tolerated in these reactions. Here, by using 3-diazooxindole as the carbene precursor, the visible-light-mediated cyclopropanation reaction of diazo compounds with electron-deficient olefins was successfully developed. The electron-rich olefins were also well tolerated in the reactions. A series of spirocyclopropyloxindoles were synthesized in moderate to high yields under mild, metal-free conditions. Mechanism studies reveal that both singlet and triplet carbenes are probably involved in the reaction.

近年来，以可见光为介导的重氮化合物与不同烯烃或炔烃的无金属环丙烷化反应得到了充分发展。然而，缺电子的烯烃在这些反应中仍然不能很好地耐受。本文以 3-重氮吲哚为碳烯前体，成功开发了重氮化合物与缺电子烯烃在可见光介导下的环丙烷化反应。富电子烯烃在反应中也有很好的耐受性。在温和、无金属的条件下合成了一系列螺环丙基吲哚，产率从中等到较高。机理研究表明，单碳原子和三碳原子可能都参与了反应。

引用次数: 0

Visible-light-promoted one-pot synthesis of β-keto sulfones from aryldiazo tetrafluoroborate salts via aerobic multicomponent reaction 通过有氧多组分反应，以芳基重氮四氟硼酸盐为原料，在可见光促进下一步合成β-酮砜

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-10 DOI: 10.1016/j.tet.2024.134303

Truong Giang Luu , Hee-Kwon Kim

β-Keto sulfone is a useful structure in organic chemistry and pharmaceuticals. In the present study, we developed a highly efficient visible-light-promoted reaction to prepare β-keto sulfones under mild conditions. Synthesis was achieved via one-pot multi-component reaction of aryldiazo tetrafluoroborate salts, alkenes, and DABSO in the presence of air (O₂) with rhodamine B serving as the photocatalyst. A variety of β-keto sulfones were obtained at high yields by this one-pot operation under aerobic atmosphere. This oxysulfonylation procedure has benefits such as mild reaction conditions, a wide tolerance of functional groups, and simplicity, making it a promising choice for preparing valuable β-keto sulfones.

β-酮砜是有机化学和制药中的一种有用结构。在本研究中，我们开发了一种在温和条件下制备 β-酮砜的高效可见光促进反应。在空气（O2）存在下，以罗丹明 B 为光催化剂，通过芳基重氮四氟硼酸盐、烯烃和 DABSO 的单锅多组分反应实现了合成。在有氧气氛下，通过这种一锅操作以较高的产率获得了多种 β-酮砜。这种氧化磺酰化过程具有反应条件温和、对官能团的耐受性广、操作简单等优点，是制备有价值的 β-酮砜的理想选择。

引用次数: 0

Attempted synthesis of the central 2,2-disubstituted pseudoindoxyl core of Austamide via a [Au]-catalyzed nitroalkyne cycloisomerization and intramolecular [3 + 2]-cycloaddition 通过[Au]催化的硝基炔环异构化和分子内[3 + 2]-环加成尝试合成奥斯特酰胺的中心 2,2-二取代假吲哚核心

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-10 DOI: 10.1016/j.tet.2024.134301

Swapnil V. Halnor, Chepuri V. Ramana

Herein, we describe an Au-catalyzed cycloisomerization process of a nitroalkyne that was projected to construct the central 2,2-disubstituted pseudoindoxyl core of the natural product Austamide. Our intended strategy for forging the pseudoindoxyl core is based on the nitroalkyne cycloisomerization followed by a subsequent intramolecular [3 + 2] cycloaddition. However, the [3 + 2] cycloaddition occurred in an undesired manner, ultimately leading to a complex hexacyclic scaffold.

在本文中，我们描述了一种金催化的硝基炔环异构化过程，预计该过程将构建天然产物 Austamide 的中心 2,2-二取代假吲哚基核心。我们打算采用硝基炔环异构化，然后进行分子内[3 + 2]环加成的方法来形成假吲哚基核心。然而，[3 + 2]环加成以不希望的方式发生，最终导致了复杂的六环支架。

引用次数: 0

Identification, structural revision and biological evaluation of the phyllocladane-type diterpenoids from Callicarpa longifolia var. floccosa 长叶胼变种中的phyllocladane型二萜的鉴定、结构修订和生物学评价

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-10-10 DOI: 10.1016/j.tet.2024.134304

Qing Li , Kun Shang , Jin Wang , Chen-Sen Xu , Zhuoer Cai , Peng Yuan , Chun-Gu Wang , Min-Min Gu , Yu Zhang , Zhi-Xin Liao

Phyllocladane-type diterpenoids represent a rare group of tetracyclic diterpenes. Two diterpenoids (1 and 2) were extracted from Callicarpa longifolia var. floccosa, along with the Chemically synthesized derivatized compound 3. The crystal data for compound 1 were first reported in this study, and compound 2 was identified as a novel phyllocladane-type diterpenoid. In addition, calliterpenone monoacetate was previously erroneously reported as compound 2. We corrected the structure of calliterpenone monoacetate to 2a by X-ray diffraction, NMR calculations, and chemical synthesis, as well as the TDDFT-ECD method. At the same time, the antitumor activity of compounds 1 and 2 was studied.

Phyllocladane 型二萜是一类罕见的四环二萜。从 Callicarpa longifolia var. floccosa 中提取了两种二萜类化合物（1 和 2），以及化学合成的衍生化合物 3。本研究首次报道了化合物 1 的晶体数据，并鉴定出化合物 2 是一种新型的phyllocladane 类二萜化合物。此外，马蹄莲酮单乙酸酯之前被错误地报告为化合物 2。我们通过 X 射线衍射、核磁共振计算、化学合成以及 TDDFT-ECD 方法，将单乙酸马来萜酮的结构更正为 2a。同时，我们还研究了化合物 1 和 2 的抗肿瘤活性。

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