Tetrahedron最新文献_第7页

Fluorescent sensors based on phenanthroline derivatives for the detection of Zn(II) ions 基于邻菲罗啉衍生物的荧光传感器检测Zn（II）离子

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-07 DOI: 10.1016/j.tet.2025.134702

Bo Yang, Yuan Tian, Ziheng Yang, Kun Jiang, Zece Zhu, Jian-Gong Yang, Wei Li

{"title":"Fluorescent sensors based on phenanthroline derivatives for the detection of Zn(II) ions","authors":"Bo Yang, Yuan Tian, Ziheng Yang, Kun Jiang, Zece Zhu, Jian-Gong Yang, Wei Li","doi":"10.1016/j.tet.2025.134702","DOIUrl":"10.1016/j.tet.2025.134702","url":null,"abstract":"<div><div>Two novel phenanthroline-based fluorescent probes, 1,2-diphenyl-1H-imidazo[4,5-f][1,10]phenanthroline (<strong>DIP</strong>) and 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (<strong>PIP</strong>), were designed and synthesized for the highly sensitive and selective detection of Zn<sup>2+</sup> in DMSO/H<sub>2</sub>O solutions. These probes exhibit remarkable detection performance, achieving an impressive detection limit of 0.10 μM while maintaining excellent selectivity against competing metal ions, attributable to their efficient interaction with Zn<sup>2+</sup>. With the addition of Zn<sup>2+</sup>, a significant bathochromic shift of 55 nm in emission maxima was displayed, accompanied by a distinct colorimetric transition from blue to cyan with fluorescence quantum yield of 13.8 %. Particularly noteworthy is <strong>DIP</strong>'s exceptional pH tolerance, maintaining its sensing capability across an unprecedented pH range from strongly acidic to alkaline conditions (pH 2–13). The binding stoichiometry and mechanism were systematically investigated through Job's plot analysis, fluorescence spectral studies, and DFT calculations. This study establishes a novel design paradigm for developing robust fluorescent probes capable of operating under extreme environmental conditions, offering promising potential for environmental monitoring and biological sensing applications.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"182 ","pages":"Article 134702"},"PeriodicalIF":2.1,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143923691","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis and biological evaluation of thiazolo[3,2-b][1,2,4]triazole substituted 1,3,4-oxadiazole and pyridine derivatives as anticancer agents 噻唑[3,2-b][1,2,4]三唑取代1,3,4-恶二唑及吡啶衍生物抗癌药物的合成及生物学评价

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-06 DOI: 10.1016/j.tet.2025.134698

Ali G. Alkhathami , S. Tasqeeruddin , Shaheen sultana , Laxminarayana Eppakayala , Nalla Somaiah

{"title":"Synthesis and biological evaluation of thiazolo[3,2-b][1,2,4]triazole substituted 1,3,4-oxadiazole and pyridine derivatives as anticancer agents","authors":"Ali G. Alkhathami , S. Tasqeeruddin , Shaheen sultana , Laxminarayana Eppakayala , Nalla Somaiah","doi":"10.1016/j.tet.2025.134698","DOIUrl":"10.1016/j.tet.2025.134698","url":null,"abstract":"<div><div>A new series of thiazolo[3,2-b][1,2,4]triazole substituted 1,3,4-oxadiazole and pyridine derivatives (<strong>17a-j</strong>) were synthesized by the cyclization of thiazolo[3,2-b][1,2,4]triazole carbohydrazide and differently substituted benzoic acids. The structures of these derivatives were characterized by <sup>1</sup>HNMR, <sup>13</sup>CNMR and mass spectral data and anticancer activities were determined by MTT assay method against human prostate cancer (PC3), human lung cancer (A549), human breast cancer (MCF-7) & human ovarian cancer (DU-145) cell lines with etoposide used as positive control. The Structure Activity Relationship studies showed that the drug candidate <strong>17a</strong> with 3,4,5-trimethoxy electron donating substituent on phenyl ring showed potent anticancer activities against PC3, A549, MCF-7 and DU-145 cell lines with IC<sub>50</sub> values of 0.14 ± 0.065 μM, 0.10 ± 0.084 μM, 0.04 ± 0.0076 μM, and 0.19 ± 0.082 μM. The compound <strong>17a</strong> was docked with the X-ray crystal structure of PDK1 with (PDB ID 1OKY) to elucidate the interactions between the small molecule and the active site residues and having a binding energy of −7.9 kcal/mol.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"183 ","pages":"Article 134698"},"PeriodicalIF":2.1,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143936793","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Phenanthrenes synthesis via Rh(Ⅲ)–Catalyzed formal [4+2] oxidative annulation of (2–arylphenyl)boronic acids with norbornadiene Rh（Ⅲ）催化（2 -芳基苯基）硼酸与降冰片二烯的正[4+2]氧化环反应合成菲

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-05 DOI: 10.1016/j.tet.2025.134701

Tianxin Hao, Wenquan Liao, Mei Liu, Li Wei, Yiyuan Peng, Qiuping Ding

引用次数: 0

Base-free palladium-catalyzed borylation of enol carboxylates and further reactivity toward deboronation and cross-coupling 无碱钯催化烯醇羧酸酯的硼化反应及其对波化和交叉偶联的反应性

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-03 DOI: 10.1016/j.tet.2025.134682

Gregory Gaube, Douglas L. Miller, Rowan A. McCallum, Nahiane Pipaón Fernández, David C. Leitch

{"title":"Base-free palladium-catalyzed borylation of enol carboxylates and further reactivity toward deboronation and cross-coupling","authors":"Gregory Gaube, Douglas L. Miller, Rowan A. McCallum, Nahiane Pipaón Fernández, David C. Leitch","doi":"10.1016/j.tet.2025.134682","DOIUrl":"10.1016/j.tet.2025.134682","url":null,"abstract":"<div><div>A series of base-free Pd-catalyzed borylation procedures are reported for a number of alkenyl carboxylates, with pivalates generally outperforming their acetate counterparts. High-throughput experimentation was used to discover and optimize these reactions using <em>in situ</em> generated catalyst systems. Mechanistic studies identified C–O oxidative addition to Pd(0) as the turnover-limiting step, with a variety of rates observed depending on substrate structure. One exemplar oxidative addition complex was isolated and fully characterized, including by X-ray crystallography. This complex undergoes rapid and complete reaction with excess B<sub>2</sub>Pin<sub>2</sub> at room temperature, confirming that no exogeneous base is required for transmetallation with the Pd(II) pivalate intermediate. Notably, gamma-lactone and lactam substrates lead to unstable alkenyl pinacol boronates, which undergo protodeboronation under acidic and basic aqueous conditions. Optimization of this protodeboronation resulted in a mild, two-step reduction of the C–O bond, achieving net-deoxygenation while leaving the alkene intact. In contrast, use of an alternative tetraalkoxydiboron source – B<sub>2</sub>EPin<sub>2</sub> – was successful in catalysis, and offered improved stability of the resulting organoboron species. This enables further reactivity, such as cross-coupling, without competing protodeboronation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"182 ","pages":"Article 134682"},"PeriodicalIF":2.1,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143923692","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Exploring the reactivity of 5,5-dimethyl-1,2-oxathiolan-4-one 2,2-dioxide and their spirocyclopropyl counterpart 探索5,5-二甲基-1,2-草酸硫胺-4- 1,2,2 -二氧化物及其螺环丙基对应物的反应性

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-05-02 DOI: 10.1016/j.tet.2025.134684

Anton O. Poliudov , Dmytro Y. Havryshko , Denys I. Krasilov , Mykyta D. Sorokin , Demyd S. Milokhov , Pavlo A. Virych , Petro A. Virych , Тaras V. Omelian , Andrii I. Kysil , Alexey V. Dobrydnev

{"title":"Exploring the reactivity of 5,5-dimethyl-1,2-oxathiolan-4-one 2,2-dioxide and their spirocyclopropyl counterpart","authors":"Anton O. Poliudov , Dmytro Y. Havryshko , Denys I. Krasilov , Mykyta D. Sorokin , Demyd S. Milokhov , Pavlo A. Virych , Petro A. Virych , Тaras V. Omelian , Andrii I. Kysil , Alexey V. Dobrydnev","doi":"10.1016/j.tet.2025.134684","DOIUrl":"10.1016/j.tet.2025.134684","url":null,"abstract":"<div><div>1,2-Oxathiolan-4-one 2,2-dioxides (put simply, β-keto γ-sultones) is the underexplored class of compounds. Within the framework of the present work, 5,5-dimethyl-1,2-oxathiolan-4-one 2,2-dioxide (<strong>1a</strong>) and 4-oxa-5-thiaspiro[2.4]heptan-7-one 5,5-dioxide (<strong>1b</strong>) were used as the model compounds whose reactivity was studied and compared in terms of strain cycle effects. Keto sultones are considered the sulfur-containing bioisosteres of naturally occurring compounds and their spirocyclic derivatives are of interest for medicinal chemistry. The reactivity of keto sultones is associated with three reaction centers: the activated methylene group, the carbonyl functionality, and the tertiary γ-carbon atom. The highly strained spirocyclopropyl substituent altered the reactivity of the keto sultone core: the reactivity of the carbonyl group was suppressed whereas the reactivity of the methylene group was greatly enhanced. The density functional theory (DFT) calculations confirmed and supplemented the experimental data. Aminomethylidene derivatives of keto sultones exhibited moderate cytotoxicity against MD Anderson-metastatic breast-231 (MDA-MB-231) breast cancer cell line. The molecular docking study rationalized the experimental <em>in vitro</em> data and predicted potential activity as anti-Parkinson's and anti-Alzheimer's disease compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134684"},"PeriodicalIF":2.1,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143903386","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

A novel aggregation-induced emission fluorescent probe for sensitive detection of pH changes in seafood freshness monitoring 一种新型聚集诱导发射荧光探针用于海鲜新鲜度监测中pH变化的灵敏检测

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-04-30 DOI: 10.1016/j.tet.2025.134700

Ziyi Zhang , Xingwen Wang , Lei Shi , Yunhe Lang , Yuexing Gao , Ruiyang Bai , Siyun Zhang , Jinkun Xi , Chao Han , Xiufeng Zhang

引用次数: 0

Domino syntheses of carbo- and heterocycles from Pd-catalyzed bis-substitutions of allylic bis-carboxylates, -carbonates or –diols 钯催化烯丙基双羧酸酯、-碳酸酯或-二醇双取代的多米诺合成羰基和杂环

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-04-30 DOI: 10.1016/j.tet.2025.134680

Jacques Muzart

引用次数: 0

Cytotoxic activity of secondary metabolites from Machaerium isadelphum and structure-activity relationship of machaeriols and machaeridiols 石竹次生代谢产物的细胞毒活性及石竹醇与石竹醇的构效关系

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-04-29 DOI: 10.1016/j.tet.2025.134694

Ihtiel Benítez-Cortés , Jaime Escalante , Gabriel Navarrete-Vazquez , Leticia González-Maya , Maria Yolanda Rios

{"title":"Cytotoxic activity of secondary metabolites from Machaerium isadelphum and structure-activity relationship of machaeriols and machaeridiols","authors":"Ihtiel Benítez-Cortés , Jaime Escalante , Gabriel Navarrete-Vazquez , Leticia González-Maya , Maria Yolanda Rios","doi":"10.1016/j.tet.2025.134694","DOIUrl":"10.1016/j.tet.2025.134694","url":null,"abstract":"<div><div><em>Machaerium isadelphum</em> is a species traditionally used in Mexican medicine for the treatment of cancer. In this study, compounds <strong>1</strong>–<strong>6</strong>, isolated from this natural source, are evaluated as potential cytotoxic agents against PC-3 (prostate cancer) and H1299 (lung cancer) cancer‐derived cells. The purification process also led to the isolation of three minor compounds with previously unreported structures (compounds <strong>7</strong>–<strong>9</strong>). The structures of <strong>7</strong>–<strong>9</strong> are elucidated through the analysis of their spectroscopic and spectrometric data, including 1D and 2D-NMR. Machaeriol A (<strong>4</strong>) and machaeridiol A (<strong>6</strong>) exhibited the highest cytotoxic activity. Their structure-activity relationship was further explored by semi-synthesizing nine derivatives (compounds <strong>10</strong>–<strong>18</strong>), which involved homologue alkylation of the hydroxyl groups and modifications to the double bond in the stilbene and monoterpene regions. The cytotoxic activity of these derivatives was compared to that of the natural products <strong>4</strong>–<strong>6</strong> and <strong>9</strong>, revealing that both hydrogenation of the double bonds and its isomerization to the <em>cis</em> form enhanced activity. Compounds <strong>6</strong>, <strong>16</strong>, and <strong>18</strong> emerged as promising cytotoxic agents.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"182 ","pages":"Article 134694"},"PeriodicalIF":2.1,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143903939","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Enshuol epoxide, an unusual squalene-derived bromotriterpene from Laurencia omaezakiana and its biological evaluation 一种罕见的角鲨烯衍生溴三萜环氧化恩舒酚及其生物学评价

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-04-29 DOI: 10.1016/j.tet.2025.134686

Tatsuhide Miwa , Tomoki Tsuruta , Chikato Nozue , Ryoma Nakagawa , Ryosuke Fukada , Keisuke Nishikawa , Yoshiki Morimoto , Momochika Kumagai , Ryunosuke Nakamura , Toshiyuki Hamada , Yukimasa Yamagishi , Takashi Kamada

{"title":"Enshuol epoxide, an unusual squalene-derived bromotriterpene from Laurencia omaezakiana and its biological evaluation","authors":"Tatsuhide Miwa , Tomoki Tsuruta , Chikato Nozue , Ryoma Nakagawa , Ryosuke Fukada , Keisuke Nishikawa , Yoshiki Morimoto , Momochika Kumagai , Ryunosuke Nakamura , Toshiyuki Hamada , Yukimasa Yamagishi , Takashi Kamada","doi":"10.1016/j.tet.2025.134686","DOIUrl":"10.1016/j.tet.2025.134686","url":null,"abstract":"<div><div>The red seaweed, <em>Laurencia omaezakiana</em>, is a rich source of secondary metabolites derived from squalene. A new brominated polyether, enshuol epoxide (<strong>1</strong>), together with two known compounds, enshuol (<strong>2</strong>) and 15,16-anhydrothyrsiferol (<strong>3</strong>), were isolated and characterized from this alga. Interestingly, we also found <em>cis</em>-chondrin (<strong>4</strong>), a non-terpenoid C<sub>15</sub> acetogenin, which has not been previously reported in this species. The gross structure and absolute configuration of <strong>1</strong> were elucidated by using spectroscopic methods, comparison with existing data, and chemical derivatization. Compounds <strong>1</strong>–<strong>3</strong>, which exhibited significant cytotoxic activities against a panel of adult T-cell leukemia (ATL) cell lines, can potentially be used to develop novel drugs for leukemia.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134686"},"PeriodicalIF":2.1,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143902567","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Photocatalytic C–H functionalization utilizing acridine−Lewis acid complexes and pyridine N-oxide based HAT catalysts 利用吖啶-路易斯酸配合物和吡啶n -氧化物基HAT催化剂光催化C-H功能化

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-04-26 DOI: 10.1016/j.tet.2025.134683

Jun Luo, Jujhar Singh, Yongming Deng

引用次数: 0