Tetrahedron Letters最新文献

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First total synthesis of acronyculatin S 首个首字母缩略词S的全合成

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-21 DOI: 10.1016/j.tetlet.2025.155868

Na Wang , Xilan Jiang , Yujiao He , Mengqi Wang , Yuanwei You , Yufei Che , Dexiu Cui , Hongbo Dong

Acronyculatin S is a naturally occurring benzofuran derivative isolated from Acronychia pedunculata and has been reported to exhibit antibacterial activity. In this study, the first total synthesis of acronyculatin S was achieved through a concise and scalable route involving a Friedel–Crafts acylation, a Sonogashira coupling, and an europium(III)-catalyzed Claisen rearrangement as key steps. However, antibacterial evaluation of the synthetic sample against a panel of Gram-positive bacterial strains revealed no significant inhibitory activity under the tested conditions (MIC > 64 μg/mL). This work provides a reliable synthetic route for accessing acronyculatin S and related analogues, facilitating further studies on the chemical and biological properties of this class of natural products.

首字母缩略词S是一种天然存在的苯并呋喃衍生物，从长尾首字母缩略词中分离出来，据报道具有抗菌活性。在这项研究中，首个首字母缩略蛋白S的全合成是通过一个简洁和可扩展的途径实现的，其中包括Friedel-Crafts酰化，Sonogashira偶联和铕（III）催化的Claisen重排作为关键步骤。然而，合成样品对一组革兰氏阳性菌株的抗菌评价显示，在测试条件下（MIC > 64 μg/mL）没有显著的抑制活性。本工作为获取首字母缩略素S及相关类似物提供了可靠的合成途径，为进一步研究该类天然产物的化学和生物学特性提供了便利。

引用次数: 0

NaH-mediated synthesis of 3-hydroxy-2-oxindoles and their analogues from ortho-iodoaryl α-ketoamides 邻碘芳基α-酮酰胺催化合成3-羟基-2-氧吲哚及其类似物的研究

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-21 DOI: 10.1016/j.tetlet.2025.155870

Mengyang He , Qihui Wang , Tingting Yi , Xiaobei Chen , Xuejun Liu , Xiaodong Chen , Shilei Zhang , Yanwei Hu

In our previous study, KH was employed as a metal-halogen exchange reagent to generate aryl anions for initiating the anionic Fries rearrangement. Herein, we demonstrate that cost-effective NaH can similarly activate ortho-iodoaryl α-ketoamide substrates via NaI exchange with the aryl iodide moiety. The resultant aryl anions undergo intramolecular cyclization, efficiently affording 3-hydroxy-2-oxindoles or their heterocyclic analogues. Notably, these products can be further converted into other types of nitrogen-containing heterocycles, thereby establishing a platform for constructing diverse biologically important heterocyclic compounds for drug discovery.

在我们之前的研究中，KH被用作金属-卤素交换试剂，生成芳基阴离子，引发阴离子Fries重排。在此，我们证明了具有成本效益的NaH可以通过NaI与芳基碘化部分交换类似地激活邻碘芳基α-酮酰胺底物。由此产生的芳基阴离子进行分子内环化，有效地提供3-羟基-2-氧吲哚或其杂环类似物。值得注意的是，这些产物可以进一步转化为其他类型的含氮杂环，从而为构建各种具有重要生物学意义的杂环化合物建立了一个平台，用于药物发现。

引用次数: 0

Gram-scale synthesis of the thiazolidinedione-based mitoNEET ligand NL-1 using a Hantzsch ester reduction 用Hantzsch酯还原法合成以噻唑烷二酮为基础的mitoNEET配体NL-1

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-18 DOI: 10.1016/j.tetlet.2025.155863

James Mersch , Yehenew Agazie , Michael A. Menze , Mary E. Konkle , Jason D. Huber , Werner J. Geldenhuys

MitoNEET (CISD1), an [2Fe-2S] cluster protein located on the outer mitochondrial membrane and known for its role in cellular redox regulation and bioenergetics, has been identified as a novel ferroptosis-related drug target in neurodegeneration and cancer. The mitoNEET ligand NEET ligand-1 (NL-1) was developed as a pharmacological tool to elucidate the biochemistry of the novel protein in a variety of disease states, ranging from oncology to neurodegenerative disorders. Here, we present a scalable gram-level synthesis of the thiazolidinedione (TZD) containing NL-1 from the precursor CI-987 using the Hantzsch ester reduction as an alternative to conventional lithium borohydride or cobalt chloride-based methods. This optimized protocol enables the reliable production of NL-1 in quantities sufficient for preclinical disease modeling.

MitoNEET （CISD1）是一种位于线粒体外膜的[2Fe-2S]簇蛋白，以其在细胞氧化还原调节和生物能量学中的作用而知名，已被确定为神经变性和癌症中与铁凋亡相关的新药物靶点。mitoNEET配体NEET配体-1 （NL-1）被开发为一种药理学工具，用于阐明从肿瘤到神经退行性疾病等各种疾病状态下新蛋白的生物化学。在这里，我们提出了一个可扩展的克级合成含有NL-1的噻唑烷二酮（TZD）从前体CI-987使用Hantzsch酯还原作为替代传统的硼氢化锂或氯化钴为基础的方法。该优化方案能够可靠地生产NL-1，其数量足以用于临床前疾病建模。

引用次数: 0

Micelle-enabled synthesis of diverse 3-substituted-3H-benzo[f]chromene constructs in water 胶束在水中合成各种3-取代- 3h -苯并[f]铬

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-17 DOI: 10.1016/j.tetlet.2025.155852

Raja Abdul Basit , Shaziya Hassan , Bilal A. Bhat

We have developed an interesting strategy to target a range of benzo[f]chromene constructs in water, which aligns with the green and sustainable chemistry ideas. The approach involves the reaction of β-naphthols with enals to furnish benzochromene constructs through a diverted reaction pathway in micellar medium compared to the reaction in conventional organic solvents. This transformation occurs within the CPB-micellar nanoreactors through the condensation of β-naphthols with enals, followed by the diene-enone electrocyclization reaction to steer benzo[f] chromene scaffolds in great precision.

我们已经开发了一种有趣的策略，以水中的苯并[f]铬结构为目标，这与绿色和可持续化学理念相一致。该方法涉及β-萘酚与烯醛在胶束介质中的反应，与在常规有机溶剂中的反应相比，通过改变的反应途径生成苯并铬。这种转化发生在cpb胶束纳米反应器内，通过β-萘酚与烯醛的缩合，然后是二烯-烯酮电环化反应，以极高的精度导向苯并[f]铬支架。

引用次数: 0

Recent advances in Chan-Evans-Lam-type synthesis of ionic compounds chan - evans - lam型离子化合物合成研究进展

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-17 DOI: 10.1016/j.tetlet.2025.155866

Ao Wen, Baobao Su, Suci Meng, Huachen Lin, Zhibin Luo, Bin Liu

Since 2021, Chan–Evans–Lam (CEL) chemistry has expanded beyond classical protic nucleophiles to enable the synthesis of diverse onium salts from weakly nucleophilic or aprotic heteroatom substrates. Copper-mediated coupling of boronic acids with nitriles, N-heterocycles, thioethers, sulfenamides, thioureas, and phosphines now delivers nitrogen-, sulfur-, and phosphorus-centered onium salts under mild conditions. These advances significantly broaden the synthetic utility of CEL reactions, while persistent challenges with tertiary amines and general ethers delineate critical frontiers for future development.

自2021年以来，Chan-Evans-Lam （CEL）化学已经扩展到超越经典的亲核试剂，能够从弱亲核或非亲核杂原子底物合成各种盐。铜介导的硼酸与腈、n-杂环、硫醚、磺胺、硫脲和膦的偶联现在在温和的条件下提供氮、硫和磷为中心的铵盐。这些进展极大地扩大了CEL反应的合成用途，而叔胺和通用醚的持续挑战描绘了未来发展的关键前沿。

引用次数: 0

Plasma-induced hybridization based on (−)-epigallocatechin as a potent anti-glycation agents 血浆诱导杂交基于(−)-表没食子儿茶素作为一种有效的抗糖化剂

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-15 DOI: 10.1016/j.tetlet.2025.155864

Gyeong Han Jeong , Tae Hoon Kim

(−)-Epigallocatechin (EGC) and sesamol hybridized products 1–3 were successfully synthesized by atmospheric pressure (ATP) plasma treatment. The chemical structures of newly hybridized products were determined by interpretation of spectroscopic data (NMR and FABMS), with the absolute stereochemistry being established by analysis of the circular dichroism (CD) spectra. The unprecedented hybrid structure sesacachin A (1) exhibited enhanced anti-glycation capacities toward the formation of advanced glycation end products (AGEs) and hydroxyl radical scavenging compared to the original (−)-EGC and sesamol. A novel hybrid product, sesacachin A (1), represents a promising subclass of anti-glycation candidates that needs further investigation.

（−）-Epigallocatechin （EGC）和sesamol杂交产物1-3通过常压（ATP）等离子体处理成功合成。新杂化产物的化学结构通过波谱数据（NMR和FABMS）分析确定，并通过圆二色性（CD）光谱分析确定绝对立体化学。与原始的(−)-EGC和芝麻酚相比，前所未有的杂交结构sesacachin A(1)在晚期糖基化终产物（AGEs）的形成和羟基自由基清除方面表现出更强的抗糖基化能力。一种新的杂交产物sesacachin A(1)代表了一个有希望的抗糖化候选亚类，需要进一步研究。

引用次数: 0

Recent advances related to purification handles for oligonucleotide separation 寡核苷酸分离纯化手柄的最新进展

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-14 DOI: 10.1016/j.tetlet.2025.155853

Yasufumi Fuchi, Yoshiyuki Hari

In solid-phase synthesis of oligonucleotides (ONs), not only the target ON but also undesired byproducts, including short-length ONs, are produced. However, because these ONs possess similar physicochemical properties, they are often difficult to separate using chromatography such as reversed-phase HPLC. To facilitate the separation of the target ON from undesired ONs, the purification handle 4,4′-dimethoxytrityl (DMTr) group has been utilized. Until now, several types of purification handles containing lipophilic groups, in addition to the DMTr group, have been reported. In this paper, recent advances and methodologies related to the purification handles for ON purification are summarized.

在固相合成寡核苷酸（ONs）的过程中，不仅会产生目标ON，还会产生不需要的副产物，包括短长度的ONs。然而，由于这些离子具有相似的物理化学性质，它们通常难以使用色谱法（如反相HPLC）分离。为了方便目标ON与不需要的ON的分离，使用了纯化手柄4,4 ' -二甲氧基三硝基（DMTr）基团。到目前为止，除了DMTr基团外，还报道了几种含有亲脂性基团的纯化手柄。本文综述了有关ON净化手柄的最新进展和方法。

引用次数: 0

A diastereoselective preparation of cyclic α-aminoboronates 环α-氨基硼酸酯的非对映选择性制备

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-10 DOI: 10.1016/j.tetlet.2025.155848

John Kim, Anna Page, Ryan T. Vanderlinden, Ryan E. Looper

Chiral α-amino- and α-amidoboronates are established pharmacophores in numerous drugs and drug candidates, however, methods to prepare this motif are limited. We report the preparation of cyclic α-amino boronates via a three-component coupling reaction of salicylaldehydes, tetrahydroxydiboron, and chiral amines. Deploying 1,2-aminoalcohol and aminoacid derivatives delivers a structurally diverse set of cyclic α-aminoboronates. Moderate to high diastereoselectivity is noted both at the newly forged carbon‑boron bond and at the tetrahedral boron center.

手性α-氨基和α-氨基硼酸盐是许多药物和候选药物中已建立的药效团，然而，制备该基序的方法有限。我们报道了通过水杨醛、四羟基二硼和手性胺的三组分偶联反应制备环α-氨基硼酸盐。部署1,2-氨基醇和氨基酸衍生物提供了一套结构多样的环α-氨基硼酸盐。在新形成的碳硼键和四面体硼中心都有中等到高的非对映选择性。

引用次数: 0

Photoinduced heptafluoroisopropylation/cyclization of unactivated alkenes towards heptafluoroisopropylated polycyclic quinazolinones by an EDA complex EDA配合物光诱导七氟异丙基/非活化烯烃环化成七氟异丙基多环喹唑啉酮

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-10 DOI: 10.1016/j.tetlet.2025.155847

Mengfei Yang , Xiaoyu Wang , Xi Chen , Xia Zhao , Jie Kang , Kui Lu

We report a photocatalyst-free radical cascade heptafluoroisopropylation/cyclization of unactivated alkenes with heptafluoroisopropyl iodides, facilitated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or N,N,N′,N′-tetramethylethane-1,2-diamine (TMEDA) as the electron donors. The reaction is compatible with a broad range of quinazolinones containing unactivated alkenes, producing the heptafluoroisopropylated polycyclic quinazolinones with the moderate to high yields. Preliminary mechanistic studies revealed that the reaction is initiated by the in situ generated electron donor-acceptor (EDA) complex.

本文报道了以1,8-重氮双环[5.4.0]十一-7-烯（DBU）或N，N ',N ' -四甲基乙烷-1,2-二胺（TMEDA）为电子供体，以七氟异丙基碘化物为光催化剂，自由基级联七氟异丙基化/环化未活化烯烃的反应。该反应与多种含非活化烯烃的喹唑啉酮相容，可制得中高收率的七氟异丙基多环喹唑啉酮。初步机理研究表明，该反应是由原位生成的电子供体-受体（EDA）复合物引发的。

引用次数: 0

Palladium-catalyzed phosphonium ylidyl-carbonylation of aryl bromides for the synthesis of α-acylphosphoranes 钯催化芳基溴基乙烯基羰基化合成α-酰基磷烷

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-10-08 DOI: 10.1016/j.tetlet.2025.155849

Xiao-Jun Guo , Rong-Xin Fan , Tian-Tian Wang , Qiu-Ya Wang , Xiu-Qin Cai , Bo Liu , Xiao-Qiang Zhou

We report a palladium-catalyzed carbonylation protocol for the synthesis of α-acylphosphoranes using low-cost aryl bromides and stabilized phosphonium ylides under 1 atm of carbon monoxide (CO). A broad range of α-acylphosphoranes can be obtained in moderate to excellent yields with good functional group tolerance under mild reaction conditions, showcasing the potential of the method in synthetic organic chemistry.

我们报道了一种钯催化羰基化方案，在1atm的一氧化碳（CO）下，使用低成本的芳基溴和稳定的酰化磷合成α-酰基磷烷。在温和的反应条件下，能以中等至优异的产率获得多种α-酰基磷烷，具有良好的官能团耐受性，显示了该方法在合成有机化学中的潜力。

引用次数: 0

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