Tetrahedron最新文献

英文中文

Synthesis of dendritic self-immolative molecules triggered by reactive electrophilic alkylating agents: Assessment for colorimetric disclosure of such agents 由活性亲电烷基化剂引发的树枝状自褪色分子的合成：评估此类制剂的比色法披露

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-14 DOI: 10.1016/j.tet.2024.134377

Alexander G. Gavriel , Flavien Leroux , Ann M. Chippindale , Mark R. Sambrook , Wayne Hayes , Andrew T. Russell

The development of efficient chemoselective self-immolative molecules for use as sensors necessitates optimization of the degradation characteristics of the self-immolative unit to permit effective signal generation (e.g. colour changes) in relation to the triggering event. One approach is to utilise degradable dendritic structures to allow multiple copies of signalling molecules to be released in return for a single triggering event. To this end, degradable isomeric dendrons featuring aniline-core units for the detection of reactive electrophilic species have been prepared and their reactions studied. A route employing protected phosphorous-borane adducts was key to their synthesis. Following deprotection of these adducts, to activate the self-immolative dendron, alkylation by an electrophilic species and subsequent elimination events, under basic conditions as employed for related molecules incapable of generating an amplified response, were investigated. These studies revealed, in contrast to the findings with other structurally-related self-immolative dendritic molecules, that the degradation profiles of these dendrons do not afford amplified responses in relation to the number of triggering events. In the light of the expenditure of resources required to generate well-defined dendritic materials, this study provides a cautionary perspective against the assumption that such branched molecules will always afford an amplified signal.

要开发出用作传感器的高效化学选择性自惰性分子，就必须优化自惰性单元的降解特性，以便根据触发事件产生有效的信号（如颜色变化）。一种方法是利用可降解树枝状结构，允许释放多份信号分子，以换取一次触发事件。为此，我们制备了以苯胺为核心单元的可降解异构树枝状结构，用于检测活性亲电物种，并对其反应进行了研究。采用受保护的磷-硼烷加合物是其合成的关键途径。在对这些加合物进行脱保护以激活自巯基树枝状化合物之后，研究人员对亲电物种的烷基化反应以及随后的消除反应进行了研究，这些反应都是在基本条件下进行的，与无法产生放大反应的相关分子的反应相同。这些研究表明，与其他结构相关的自惰性树枝状分子的研究结果相反，这些树枝状分子的降解曲线与触发事件的数量无关，不会产生放大反应。鉴于生成定义明确的树突材料需要耗费大量资源，本研究提出了一个警示性观点，即不要认为这类支化分子总能提供放大的信号。

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引用次数: 0

Michael reaction of enyne derivatives of Meldrum's acid in water: Synthetic approach for creating a C–N/C–S bonds inwith low reactive nucleophiles Meldrum's 酸的炔衍生物在水中的迈克尔反应：在低活性亲核物中生成 C-N/C-S 键的合成方法

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-14 DOI: 10.1016/j.tet.2024.134369

Sergey A. Sokov , Gulnara Z. Raskildina , Anna V. Vologzhanina , Simon S. Zlotskii , Alexander A. Golovanov

The mild addition at the triple bond of low reactive amines and thiols to 5-(Prop-2-yn-1-yliden)-2,2-dimethyl-1,3-dioxane-4,6-diones (such as 4-nitroaniline, diphenylamine, 2-mercaptobenzothiazole, and others) in aqueous medium results easily in corresponding Michael adducts in up to 99 % yields. Reactivity estimation results for Meldrum's acid enyne derivatives allow to place them among the most powerful acetylenic Michael acceptors (like DMAD). The authors have also shown regioselectivity for the addition of several bifunctional derivatives of imidazole and benzimidazole to enynes with the C–S bond formation. Polycentric nature of substrates and amine products, together with the fact of the 1,3-dioxane-4,6-dione fragment presence, provide extended options for chemical transformations of Meldrum's acid enyne derivatives to apply widely in the direct synthesis.

在水介质中，低活性胺和硫醇与 5-(丙-2-炔-1-亚基)-2,2-二甲基-1,3-二恶烷-4,6-二酮（如 4-硝基苯胺、二苯胺、2-巯基苯并噻唑等）的三键温和加成，很容易生成相应的迈克尔加合物，收率高达 99%。对 Meldrum 的酸性炔衍生物的反应活性估计结果使它们跻身于最强大的乙炔迈克尔受体（如 DMAD）之列。作者还证明了咪唑和苯并咪唑的几种双功能衍生物与炔烃加成 C-S 键的区域选择性。底物和胺产物的多中心性质，以及 1,3-二恶烷-4,6-二酮片段的存在，为梅氏酸性炔衍生物的化学转化提供了更多的选择，可广泛应用于直接合成。

引用次数: 0

Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes 用于苯并[b]氮杂卓和 1，3-共轭二烯歧化合成的催化剂控制型可切换形式逆-布赫纳反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-13 DOI: 10.1016/j.tet.2024.134378

Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie

Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with N-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[b]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.

在此，我们成功开发了一种由膦催化剂控制的甲基溴碳酸盐与 N-磺酰基氮杂七烯烃的可切换形式逆-布赫纳反应，该反应提供了一条以中等至高产率获得有价值的苯并[b]氮杂卓和多种取代的 1，3-共轭二烯衍生物的不同而有效的途径。此外，这些方法的特点还包括反应条件温和、不含过渡金属、操作简便、对官能团有广泛的耐受性以及适合克级合成。

引用次数: 0

An orthoformate-bridged bis-diazeniumdiolates: Enhanced nitric oxide loading and released NO under physiological conditions 一种原甲酸酯桥接的双偶氮二元醇：生理条件下增强的一氧化氮负荷和释放的一氧化氮

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-10 DOI: 10.1016/j.tet.2024.134367

En Chen , Qi Zhu , Luyi Zhan , Jun Chen , Huajing Lv , Wenteng Chen , Yongping Yu

Diazeniumdiolates are highly valued as NO donors in biomedical applications because of their exceptional NO-loading efficiency. Typically, the NO-releasing properties of these compounds can be tailored by incorporating various substitutes at the O²-position of N-diazeniumdiolates. In this study, we report a novel class of bis-diazeniumdiolates, which are covalently linked through an orthoformate-bridge between two diazeniumdiolate groups. Under physiological conditions (pH = 7.4, 37 ^°C), these orthoformate-bridged bis-diazeniumdiolates were found to release four equivalents of NO. The half-lives of NO release varied between 1.3 and 17.9 min. Furthermore, these bis-diazeniumdiolates exhibited superior bactericidal activity against Escherichia coli (MIC = 1–8 mM, MBC = 8–32 mM) and Staphylococcus aureus (MIC = 2–8 mM, MBC = 16–32 mM) compared to the commercial 2-(N, N-diethylamino)-diazenolate-2-oxide, which only releases two equivalents of NO per molecular (MIC _{(E. coli)} = 32 mM, MIC _(S.aureus) = 64 mM, MBC = 128 mM). These bis-diazeniumdiolates enhance NO loading and release NO independently of enzymes or chemical additives, indicating their potential benefits for further biomedical applications.

在生物医学应用中，二氮杂环戊烷因其卓越的氮氧化物负载效率而被高度评价为氮氧化物供体。通常情况下，这些化合物的氮氧化物释放特性可以通过在 N-二氮杂环戊烯的 O2 位加入各种替代物来定制。在本研究中，我们报告了一类新型的双二偶氮二酸盐，它们通过两个二偶氮二酸盐基团之间的原甲酸桥共价连接。在生理条件下（pH = 7.4，37 °C），这些原甲酸桥双偶氮二酸盐可释放四当量的 NO。释放 NO 的半衰期在 1.3 到 17.9 分钟之间。此外，与商业化的 2-（N，N-二乙基氨基）-diazenolate-2-氧化物相比，这些双二苯二酚对大肠杆菌（MIC = 1-8 mM，MBC = 8-32 mM）和金黄色葡萄球菌（MIC = 2-8 mM，MBC = 16-32 mM）具有更强的杀菌活性。大肠杆菌）= 32 mM，MIC（金黄色葡萄球菌）= 64 mM，MBC=128 mM）。这些双二偶氮二氧化物能提高氮氧化物的负载量并释放氮氧化物，而不依赖于酶或化学添加剂，这表明它们具有进一步应用于生物医学的潜在优势。

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引用次数: 0

Bio-synthesized Fe(0)/Fe2O3 composite nanoparticles as a catalyst towards the preparation of dihydropyridine derivatives under solvent-free condition at room temperature 以生物合成的 Fe(0)/Fe2O3 复合纳米粒子为催化剂，在室温无溶剂条件下制备二氢吡啶衍生物

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-10 DOI: 10.1016/j.tet.2024.134365

Partha Sarathi Bera, Jharna Mahato, Tanmoy Kumar Saha

A sustainable and innovative approach has been developed for synthesizing of Fe(0)/Fe₂O₃ composite nanoparticles (Fe(0)/Fe₂O₃NPs), utilizing the bark extract of the arjun tree (Terminalia arjuna) as a reducing and capping agent. This environmentally friendly Fe(0)/Fe₂O₃NPs was thoroughly characterized using various analytical techniques, including UV–Visible spectroscopy, FT-IR, PXRD, HR-TEM, SEM, and XPS. The nanoparticles were then evaluated as catalysts for facilitating the three-component Hantzsch reaction with acetylacetone, ammonium acetate, and substituted aldehydes, producing bioactive dihydropyridine derivatives. The catalyst exhibited high performance over approximately five cycles, with negligible loss in yield and catalytic efficiency. Additionally, a mechanistic pathway was proposed and elucidated through intermediate mass analysis, supported by Density Functional Theory (DFT) calculations.

利用阿尔琼树（Terminalia arjuna）树皮提取物作为还原剂和封端剂，开发了一种可持续的创新方法来合成 Fe(0)/Fe2O3 复合纳米粒子（Fe(0)/Fe2O3NPs）。利用各种分析技术，包括紫外可见光谱、傅立叶变换红外光谱、PXRD、HR-TEM、SEM 和 XPS，对这种环保型 Fe(0)/Fe2O3NPs 进行了全面表征。然后评估了纳米颗粒作为催化剂促进与乙酰丙酮、乙酸铵和取代醛的三组分 Hantzsch 反应，生成具有生物活性的二氢吡啶衍生物的情况。该催化剂在大约五个周期内表现出高性能，产率和催化效率的损失可以忽略不计。此外，在密度泛函理论（DFT）计算的支持下，通过中间质量分析，提出并阐明了一种机理途径。

引用次数: 0

Synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia 从海洋海绵 Halichondria melanodocia 中分离出的吲哚生物碱的合成

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-10 DOI: 10.1016/j.tet.2024.134368

Gordon W. Gribble, Stephen W. Wright

We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia, using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a sp² iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds.

我们描述了首次成功合成从海洋海绵 Halichondria melanodocia 中分离出的吲哚生物碱的过程，该过程使用了以前未报道过的α-溴酮与 sp2 碘化物在镍催化下的交叉亲电子偶联，从而提供了碳框架的趋同合成，且不会同时发生烯烃迁移。因此，吲哚生物碱是由已知化合物分两步合成的。

引用次数: 0

Anthelmintic activity of selected neolignans and semisynthetic derivatives from Styrax suberifolius 从鼠李属植物中提取的部分新木质素及其半合成衍生物的驱虫活性

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-09 DOI: 10.1016/j.tet.2024.134366

Kanchana Wijesekera , Aya C. Taki , Joseph J. Byrne , Jonathan M. White , Anthony R. Carroll , Robin B. Gasser , Rohan A. Davis

The plant metabolite, equiselignan B (2), isolated from the fruits of Styrax suberifolius was used to generate a semisynthetic library. Extraction and purification studies yielded large quantities (∼70 mg) of 2, a new glycoside, suberifolioside A (1), and the previously described neolignan egonol (3). The planer structure of 1 was established following 1D/2D NMR and MS analyses, and its absolute configuration was determined by X-ray diffraction studies. Acid hydrolysis of 1 yielded an additional amount of scaffold 2 (436 mg) that was subsequently converted into seven new ether derivatives (4–10) and two new ester derivatives (11–12) using commercially available alkyl halides and acyl chlorides, respectively. The chemical structures of the new semisynthetic ether and ester derivatives were assigned by spectroscopic and spectrometric analyses. Subsequently, compounds 1–12 were evaluated for their anthelmintic activity on exsheathed third-stage larvae (xL3s) and fourth-stage larvae (L4s) of Haemonchus contortus (barber's pole worm) – a highly pathogenic parasitic roundworm of ruminant livestock. Ether derivative 5 displayed significant anthelmintic activity against both xL3s and L4s, resulting in a 66–73 % reduction in motility at 50 μM after 168 h (xL3s) or 90 h (L4s) of exposure and IC₅₀ values of 24–30 μM. This derivative also induced curved (Cur), evisceration (Evi) and skinny (Ski) phenotypes in affected larvae. Compounds 1, 9 and 12 also had marked activity against L4s, which indicate that the neolignan structure class warrants further investigation for anthelmintic activity.

我们利用从鼠李属（Styrax suberifolius）果实中分离出的植物代谢物马钱子苷 B（2）生成了一个半合成文库。萃取和纯化研究得到了大量（∼70 毫克）2、一种新的苷类--苏木防己苷 A（1）和之前描述过的新木质素 egonol（3）。通过一维/二维核磁共振和质谱分析，确定了 1 的平面结构，并通过 X 射线衍射研究确定了其绝对构型。对 1 进行酸水解后，又得到了一定量的支架 2（436 毫克），随后利用市售的烷基卤化物和酰基氯化物分别将其转化为 7 种新的醚衍生物（4-10）和 2 种新的酯衍生物（11-12）。通过光谱和分光分析，确定了新的半合成醚和酯衍生物的化学结构。随后，评估了化合物 1-12 对反刍家畜的高致病性寄生蛔虫--轮虫（理发杆虫）的出鞘三龄幼虫（xL3s）和四龄幼虫（L4s）的驱虫活性。醚衍生物 5 对 xL3s 和 L4s 均显示出显著的驱虫活性，在接触 50 μM 时，xL3s 和 L4s 在 168 小时（xL3s）或 90 小时（L4s）后的蠕动减少了 66-73 %，IC50 值为 24-30 μM。该衍生物还诱导受影响幼虫出现弯曲（Cur）、剥离（Evi）和瘦小（Ski）表型。化合物 1、9 和 12 对 L4s 也有明显的活性，这表明新木质素结构类化合物的抗蠕虫活性值得进一步研究。

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引用次数: 0

Recent developments in the metal-free synthesis of oxazoles 草唑无金属合成的最新进展

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-09 DOI: 10.1016/j.tet.2024.134363

Pravin J. Wanjari , Kriti Mehta , Marudhvathi Kudumula , Rohit Sharma , Prasad V. Bharatam

Oxazoles found a very prominent position in heterocyclic and medicinal chemistry. Several methods of synthesizing these species were introduced, and recent efforts have been made to generate these species using metal-free methods in a highly efficient manner. In the past decade, many novel metal-free methods of synthesizing oxazoles have been emerged. A cursory glance at these methods indicated that it is possible to classify the reported methods on the basis of the proposed mechanisms. This review provides an overview of all these methods along with mechanistic details and tries to find some commonalities among these.

噁唑在杂环化学和药物化学中占有非常重要的地位。人们提出了几种合成这些化合物的方法，最近又在努力使用无金属方法高效生成这些化合物。在过去十年中，出现了许多合成噁唑的新型无金属方法。对这些方法的粗略浏览表明，可以根据所提出的机制对已报道的方法进行分类。本综述概述了所有这些方法以及机理细节，并试图找出其中的一些共性。

引用次数: 0

Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides 可回收 Ag/GO-NH2 与胺和 H-膦氧化物催化苄醇的多组分氨基膦酰化反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134359

Qiang Huang , Lei Zhu , Zhonghua Shi , Xin Jin , Wenwu Zhong

An Ag nanoparticles immobilized heterogeneous composite (Ag/GO-NH₂) was synthesized by anchoring nitrogen-containing small molecule onto graphene. The prepared Ag/GO-NH₂ was characterized by FT-IR, XRD, SEM and TEM, identifying its structure and composition. Remarkably, the Ag/GO-NH₂ composite emerged as a heterogeneous catalyst, they can promote the multi-component aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides. This heterogeneous catalytic system demonstrated good functional group tolerance and broad substrate scope, affording various α-aminophosphine oxides in good yields. Additionally, the nanocatalyst can be recovered and reused without significant decrease performance of the reaction. It offers an alternative and promising strategy for the heterogeneous synthesis of α-aminophosphine oxides.

通过将含氮小分子锚定在石墨烯上，合成了一种固定银纳米颗粒的异质复合材料（Ag/GO-NH2）。通过傅立叶变换红外光谱（FT-IR）、X射线衍射（XRD）、扫描电镜（SEM）和电子显微镜（TEM）对制备的Ag/GO-NH2进行了表征，确定了其结构和组成。值得注意的是，Ag/GO-NH2 复合材料是一种异相催化剂，它们能促进苄醇与胺和 H-膦氧化物的多组分氨基膦酰化反应。这种异相催化体系具有良好的官能团耐受性和广泛的底物范围，能以良好的产率获得各种α-氨基膦氧化物。此外，这种纳米催化剂可以回收和重复使用，而不会明显降低反应性能。它为α-氨基膦氧化物的异构合成提供了一种可供选择且前景广阔的策略。

引用次数: 0

Electrochemical-promoted Mannich-type three-component reaction of benzo-fused cyclic amides using methanol as C1 source instead of formaldehyde 用甲醇代替甲醛作为 C1 源，电化学促进苯并融合环酰胺的曼尼希式三组分反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134357

Yahui Sang , Jinjin Zhang , Mengjia Zhao , Haijuan Qin , Chao Chen , Wei Liu

The three-component N-Mannich reaction is provided in an electrochemical variant. The corresponding N-Mannich base products were obtained by the one-pot method of benzo-fused cyclic amides with secondary amines under a small current of 3 mA using methanol as the carbon source. The reaction is simple to carry out (room temperature and air environment) and requires no supporting electrolytes, using TEMPO as the oxidizing agent. The substrate scope is wide, and the yield is good (39 cases, up to 99 %). CV experiments show that secondary amines are oxidized first at the anode. Moreover, this reaction can be scaled up to the grams.

三组分 N-Mannich 反应以电化学变体的形式出现。以甲醇为碳源，在 3 mA 的小电流下，通过苯并融合环酰胺与仲胺的一锅法获得了相应的 N-Mannich 碱产物。该反应以 TEMPO 为氧化剂，操作简单（室温和空气环境），无需辅助电解质。底物范围广，产率高（39 例，高达 99%）。CV 实验表明，仲胺首先在阳极被氧化。此外，该反应还可以放大到克级。

引用次数: 0

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