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Synthesis of 7-trifluoromethyl-6H-chromeno[4,3-b]quinolin-6-ones 7-三氟甲基- 6h -氨基[4,3-b]喹啉-6-酮的合成
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-24 DOI: 10.1016/j.tet.2025.134843
Sajid Ali, Tariq M. Babar, Martin Hein, Alexander Villinger, Peter Ehlers, Peter Langer
{"title":"Synthesis of 7-trifluoromethyl-6H-chromeno[4,3-b]quinolin-6-ones","authors":"Sajid Ali,&nbsp;Tariq M. Babar,&nbsp;Martin Hein,&nbsp;Alexander Villinger,&nbsp;Peter Ehlers,&nbsp;Peter Langer","doi":"10.1016/j.tet.2025.134843","DOIUrl":"10.1016/j.tet.2025.134843","url":null,"abstract":"<div><div>The extension of the scope of reactions of 4-chloro-3-(trifluoroacetyl)coumarin with a variety of heterogeneously substituted anilines to yield 3-(trifluoroacetyl)-4-(arylamino)-2<em>H</em>-chromen-2-ones is described which were then transformed to 7-(trifluoromethyl)-6<em>H</em>-chromeno[4,3-<em>b</em>]quinolin-6-ones by acid-mediated cyclization. The regioselectivity of the cyclization reaction was studied and following Suzuki and Sonogashira reactions of halogenated products were carried out which afforded the corresponding arylated and alkynylated derivatives.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"186 ","pages":"Article 134843"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144738296","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
Rapid access to arynes from aryl triflates using a non-competitive, commercially available amide base 从芳基三氟酸盐中快速获得芳烃，使用非竞争性的，市售的酰胺基
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-24 DOI: 10.1016/j.tet.2025.134856
Bryan E. Metze, Cheryl Farris, Joseph Hatton, David R. Stuart
{"title":"Rapid access to arynes from aryl triflates using a non-competitive, commercially available amide base","authors":"Bryan E. Metze,&nbsp;Cheryl Farris,&nbsp;Joseph Hatton,&nbsp;David R. Stuart","doi":"10.1016/j.tet.2025.134856","DOIUrl":"10.1016/j.tet.2025.134856","url":null,"abstract":"<div><div>Arynes are novel intermediates for organic synthesis and aryl triflates are potentially useful aryne precursors because they are commercially available or easily prepared from widely abundant phenols. However, strong bases, which are also competitive arynophiles, are often used to generate arynes from aryl triflates and this can limit their use in synthesis. We have found that the commercially available lithium bis(trimethylsilyl)amide is uniquely non-competitive among this class of base in generating arynes from aryl triflates. We demonstrate that this method is compatible with 15 aryl triflates and 6 different arynophiles in yields ranging from 54 to 96 % (75 % avg). Moreover, we parameterize several common bases used to generate arynes from aryl triflates on an arynophilicity scale, and we describe the overall robustness of this process relative to other aryne forming reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"186 ","pages":"Article 134856"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144749940","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
Design and synthesis of Schiff base AIE fluorescent probe for the detection of exogenous and endogenous H2O2 in tumor cells 用于检测肿瘤细胞外源性和内源性H2O2的希夫碱AIE荧光探针的设计与合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-23 DOI: 10.1016/j.tet.2025.134861
Fengqing Yang , Yulong Yang , Likang Zhang , Jiali Tao , Xiaozhen Gao , Fenfen Liang , Jin Chang , Dezhi Shi , Mingxia Zhao , Junbing Jiang
{"title":"Design and synthesis of Schiff base AIE fluorescent probe for the detection of exogenous and endogenous H2O2 in tumor cells","authors":"Fengqing Yang ,&nbsp;Yulong Yang ,&nbsp;Likang Zhang ,&nbsp;Jiali Tao ,&nbsp;Xiaozhen Gao ,&nbsp;Fenfen Liang ,&nbsp;Jin Chang ,&nbsp;Dezhi Shi ,&nbsp;Mingxia Zhao ,&nbsp;Junbing Jiang","doi":"10.1016/j.tet.2025.134861","DOIUrl":"10.1016/j.tet.2025.134861","url":null,"abstract":"<div><div>In this work, a Schiff base AIE fluorescent probe (<strong>Compound 2</strong>)was designed and synthesized for detecting H<sub>2</sub>O<sub>2</sub>. The synthesis process of the probe was described in detail and characterized by <sup>1</sup> H NMR, <sup>13</sup> C NMR and HRMS. The performance (spectral properties, AIE property, concentration titration test, detection limit, selectivity and anti-interference capability, effect of pH and temperature, and response time) of the probe was extensively investigated. The <strong>Compound 2</strong> not only had excellent selectivity, sensitivity and special selectivity for detecting H<sub>2</sub>O<sub>2</sub>, but also had good anti-interference ability to pH and temperature. Biological experiments had proved that the probe had low cytotoxicity, and successfully achieved the detection of exogenous and endogenous H<sub>2</sub>O<sub>2</sub> in tumor cells and zebrafish, which would realize the early tumor diagnosis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134861"},"PeriodicalIF":2.1,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713314","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 of rare−earth metal amido complexes with methyl substituted α-iminopyridine and their catalytic activities for hydroboration of nitriles 甲基取代α-亚氨基吡啶稀土金属酰胺配合物的合成及其对腈硼氢化反应的催化活性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-23 DOI: 10.1016/j.tet.2025.134857
Donghan Wang, Xiuli Zhang, Lijun Zhang, Qingbing Yuan, Shuangliu Zhou
{"title":"Synthesis of rare−earth metal amido complexes with methyl substituted α-iminopyridine and their catalytic activities for hydroboration of nitriles","authors":"Donghan Wang,&nbsp;Xiuli Zhang,&nbsp;Lijun Zhang,&nbsp;Qingbing Yuan,&nbsp;Shuangliu Zhou","doi":"10.1016/j.tet.2025.134857","DOIUrl":"10.1016/j.tet.2025.134857","url":null,"abstract":"<div><div>The reaction of [(Me<sub>3</sub>Si)<sub>2</sub>N]<sub>3</sub>RE(<em>μ</em>−Cl)Li(THF)<sub>3</sub> with 6-CH<sub>3</sub>-2-[(CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NHCH<sub>2</sub>]C<sub>5</sub>H<sub>3</sub>N (<strong>1</strong>) or 5-CH<sub>3</sub>-2-[(CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NHCH<sub>2</sub>]C<sub>5</sub>H<sub>3</sub>N (<strong>2</strong>) resulted in the formation of rare−earth metal amido complexes bearing the dianionic <em>α</em>-iminopyridine {(<em>μ</em>-<em>η</em><sup>2</sup>:<em>σ</em><sup>1</sup>:<em>κ</em><sup>1</sup>:<em>κ</em><sup>1</sup>)(6-CH<sub>3</sub>-2-[(CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NCH]C<sub>5</sub>H<sub>3</sub>N)RE[N(SiMe<sub>3</sub>)<sub>2</sub>]}<sub>2</sub> (RE = Y(<strong>3a</strong>), Sm(<strong>3b</strong>), Gd(<strong>3c</strong>), Er(<strong>3d</strong>), Pr(<strong>3e</strong>)) or {(<em>μ</em>-<em>η</em><sup>2</sup>:<em>σ</em><sup>1</sup>:<em>κ</em><sup>1</sup>:<em>κ</em><sup>1</sup>)(5-CH<sub>3</sub>-2-[(CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NCH]C<sub>5</sub>H<sub>3</sub>N)RE[N(SiMe<sub>3</sub>)<sub>2</sub>]}<sub>2</sub> (RE = Y(<strong>4a</strong>), Sm(<strong>4b</strong>), Gd(<strong>4c</strong>), Er(<strong>4d</strong>)) through deprotonation and C–H bond activation of the 2-(aminomethylene)pyridine. These results indicated that the methyl substituent on the pyridine ring, whether at the 5- or 6-position, did not influence the deprotonation and C–H bond activation of 2-(aminomethylene)pyridine. Further investigation of the dianionic <em>α</em>-iminopyridine rare−earth metal amido complexes revealed that they exhibited exceptional catalytic activity for the hydroboration of nitriles with pinacolborane (HBpin). Especially, the catalytic process generated two types of completely different hydroboration products by controlling the different stoichiometric ratio of HBpin to nitriles.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134857"},"PeriodicalIF":2.1,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713181","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
Catalytic copper(I) alkyne-azide cycloaddition (CuAAC) utilizing arylazothioformamide ligand complexes 利用芳偶氮硫代甲酰胺配体配合物催化铜(I)炔叠氮化环加成（CuAAC）
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-23 DOI: 10.1016/j.tet.2025.134860
Rabina Pradhan , Caleb Zando , Laxmi Tiwari , Sydney Schoth , Elliott B. Hulley , Kristopher V. Waynant
{"title":"Catalytic copper(I) alkyne-azide cycloaddition (CuAAC) utilizing arylazothioformamide ligand complexes","authors":"Rabina Pradhan ,&nbsp;Caleb Zando ,&nbsp;Laxmi Tiwari ,&nbsp;Sydney Schoth ,&nbsp;Elliott B. Hulley ,&nbsp;Kristopher V. Waynant","doi":"10.1016/j.tet.2025.134860","DOIUrl":"10.1016/j.tet.2025.134860","url":null,"abstract":"<div><div>Azothioformamide (ATF) ligands have been shown to rapidly coordinate with copper(I) salts through a 1,3-diazothiocarbonyl moiety to form stable copper(I) complexes. In this work, a dimeric complex derived from <em>p</em>-methoxyphenyl azothioformamide (<em>p-</em>MeOATF) ligands and copper(I) iodide was employed as a catalyst for an aqueous three component copper(I) alkyne-azide cycloaddition (CuAAC) reaction. Reaction optimization identified that using 2 mol% of the [(<em>p-</em>MeOATF)CuI]<sub>2</sub> complex and 1.2 equiv. each of the alkyl halide and sodium azide in 1:1 water/methanol as solvent for 24 h gave high yields of 1,2,3-triazole products with 11 examples ranging in yields of 60–93 %. As ATFs are known to oxidatively remove metals from materials, the removal of copper during the formal synthesis of the pharmaceutical rufinamide was tested as to offer a promising approach to limiting copper content in CuAAC reaction products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134860"},"PeriodicalIF":2.1,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144704351","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 of 2-substituted 3-acylindoles via reductive cyclization – rearrangement of β-acyl β-alkyl-substituted 2-nitrostyrenes 还原环化法合成2-酰基β-烷基取代2-硝基苯乙烯
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-23 DOI: 10.1016/j.tet.2025.134838
S.M. Ashikur Rahman , Novruz G. Akhmedov , Ryan M. Ferguson , Björn C.G. Söderberg
{"title":"Synthesis of 2-substituted 3-acylindoles via reductive cyclization – rearrangement of β-acyl β-alkyl-substituted 2-nitrostyrenes","authors":"S.M. Ashikur Rahman ,&nbsp;Novruz G. Akhmedov ,&nbsp;Ryan M. Ferguson ,&nbsp;Björn C.G. Söderberg","doi":"10.1016/j.tet.2025.134838","DOIUrl":"10.1016/j.tet.2025.134838","url":null,"abstract":"<div><div>A short synthetic sequence to 2-substituted 3-acylindoles has been developed. The sequence starts with a Wittig or an aldol reaction of 2-nitrobenzaldehydes to give β-acyl-β-alkyl-substituted 2-nitrostyrenes. The styrenes are transformed into 2-substituted 3-acylindoles by a palladium – catalyzed, carbon monoxide – mediated, reductive cyclization with concurrent migration of the acyl group. In addition to indoles, quinoline-<em>N</em>-oxides and quinolines were sometimes obtained in low isolated yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134838"},"PeriodicalIF":2.2,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144724958","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
Fluorescence switch for silver ion and pyridine sensing 荧光开关银离子和吡啶传感
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-22 DOI: 10.1016/j.tet.2025.134855
Yingjie Liu , Shan Xiao , Qingxiang Liu
{"title":"Fluorescence switch for silver ion and pyridine sensing","authors":"Yingjie Liu ,&nbsp;Shan Xiao ,&nbsp;Qingxiang Liu","doi":"10.1016/j.tet.2025.134855","DOIUrl":"10.1016/j.tet.2025.134855","url":null,"abstract":"<div><div>A double-arm anthracene, 9,10-bis(1′-picolylbenzimidazolium-ethoxyl)anthracene hexafluorophosphate (<strong>L</strong>), was synthesized and characterized. Fluorescence switch of <strong>L</strong> under the induction of Ag<sup>+</sup> and pyridine (<strong>Py</strong>) was studied. Compound <strong>L</strong> displayed a strong fluorescence emission at 390–550 nm. Upon adding Ag<sup>+</sup>to the solution of <strong>L</strong>, the fluorescence intensity of <strong>L</strong> decreased remarkably due to the formation of <strong>LAg<sup>+</sup></strong>. Then, as pyridine was gradually added, the fluorescence intensity of <strong>LAg<sup>+</sup></strong>gradually increased until the fluorescence intensity approached that of <strong>L</strong>, where <strong>LAg</strong><sup>+</sup><strong>Py</strong> was formed. Throughout the entire process, the fluorescence of <strong>L</strong> showed a change from \"on\" to \"off\" and then back to \"on\" under the induction of Ag<sup>+</sup> and pyridine.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134855"},"PeriodicalIF":2.1,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144703896","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 relay strategy involving electrochemically driven selenylation cyclization and Cu(II) catalyzed cycloaddition-isomerization processes for the synthesis of polysubstituted isoquinolines 采用电化学驱动硒化环化和Cu（II）催化环加成异构化的接力策略合成多取代异喹啉
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-22 DOI: 10.1016/j.tet.2025.134846
Weiguang Kong, Yannian Zhou, Yi Cao, Xiaowen Yu, Caixia Yu, Runhan Li, Heyun Sheng, Ting Li, Huanping Xie
{"title":"A relay strategy involving electrochemically driven selenylation cyclization and Cu(II) catalyzed cycloaddition-isomerization processes for the synthesis of polysubstituted isoquinolines","authors":"Weiguang Kong,&nbsp;Yannian Zhou,&nbsp;Yi Cao,&nbsp;Xiaowen Yu,&nbsp;Caixia Yu,&nbsp;Runhan Li,&nbsp;Heyun Sheng,&nbsp;Ting Li,&nbsp;Huanping Xie","doi":"10.1016/j.tet.2025.134846","DOIUrl":"10.1016/j.tet.2025.134846","url":null,"abstract":"<div><div>Isoquinoline and isoquinoline <em>N</em>-oxide are core skeletons of numerous biologically active molecules and extensively utilized in organic synthesis. The development of efficient synthetic methods for these valuable building blocks has attracted significant interest within chemical community. In this study, we have developed a relay process which encompasses the electrochemically driven selenylation cyclization reaction of 2-alkynylbenzaldoximes with diselenides and the Cu(II) catalyzed cycloaddition-isomerization reaction of 4-selenylisoquinoline-<em>N</em>-oxides with bicyclobutane derivatives, thereby enabling the synthesis of isoquinolines bearing selenyl, cyclobutanol, and other groups. This protocol is characterized by mild reaction conditions, remarkable stereospecificity, a broad substrate scope, and excellent functional group tolerance. Furthermore, the high efficiency of this reaction in substrates bearing biologically relevant moieties and the successful scale-up experiment readily demonstrate its application potential.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134846"},"PeriodicalIF":2.1,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144685580","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
Dipenipenoids C and D, new dimeric indole-diterpenoids from the marine-derived fungus Penicillium sp. CF-06 海洋真菌青霉属（Penicillium sp. CF-06）中新的二聚吲哚二萜类化合物C和D
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-21 DOI: 10.1016/j.tet.2025.134850
Quan-Shui Wang , Wen-Bin Gao , Hong-Yan Gu , Zhi-Qin Liu , Fei Cao
{"title":"Dipenipenoids C and D, new dimeric indole-diterpenoids from the marine-derived fungus Penicillium sp. CF-06","authors":"Quan-Shui Wang ,&nbsp;Wen-Bin Gao ,&nbsp;Hong-Yan Gu ,&nbsp;Zhi-Qin Liu ,&nbsp;Fei Cao","doi":"10.1016/j.tet.2025.134850","DOIUrl":"10.1016/j.tet.2025.134850","url":null,"abstract":"<div><div>Two new dimeric indole-diterpenoids, dipenipenoids C and D (<strong>1</strong> and <strong>2</strong>), were obtained from the marine-derived fungus <em>Penicillium</em> sp. CF-06 by modulating fermentation conditions. Compounds <strong>1</strong> and <strong>2</strong> represent a rare and complex type of dimeric indole-diterpenoids with a C-20–C-22′ linkage. The absolute configurations of them were determined by the calculated ECD method. Compounds <strong>1</strong> and <strong>2</strong> exhibited potent effects on the differentiation of 3T3-L1 adipocytes, with lipid accumulation reduced to 92.3–16.4 % and 82.4–16.4 % at concentrations of 6.3, 12.5, 25.0, and 50.0 μM, respectively, which could provide new insights and opportunities for drug discovery in the anti-obesity arena.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134850"},"PeriodicalIF":2.1,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144703895","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
Tinocrinoids A-D, clerodane diterpenoids from Tinospora crispa and structural revision of related diterpenoid crispa Tinospora中的tinocinooids A-D、clerodane二萜及其相关二萜的结构修正
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-21 DOI: 10.1016/j.tet.2025.134851
Ming-Jie Huang, Yi-Ke Yin, Yi-Fei Zhang, Jie Bao, Jun-Sheng Zhang, Hua Zhang
{"title":"Tinocrinoids A-D, clerodane diterpenoids from Tinospora crispa and structural revision of related diterpenoid","authors":"Ming-Jie Huang,&nbsp;Yi-Ke Yin,&nbsp;Yi-Fei Zhang,&nbsp;Jie Bao,&nbsp;Jun-Sheng Zhang,&nbsp;Hua Zhang","doi":"10.1016/j.tet.2025.134851","DOIUrl":"10.1016/j.tet.2025.134851","url":null,"abstract":"<div><div>Four new clerodane diterpenoids, tinocrinoids A−D (<strong>2</strong>−<strong>5</strong>), were isolated from the leaves of <em>Tinospora crispa</em>. Compounds <strong>3</strong>−<strong>5</strong> represents rare clerodane diterpenoids with a C-8-<em>O</em>-C-12 ether bridge. The structures of the new diterpenoids were elucidated using spectral analysis in conjunction with NMR/ECD calculations and X-ray crystallography. The application of computational methods, enhanced by the DP4+ probability approach, made it possible to propose a structural revision for the known diterpenoid, tinobakisin. Evaluation of their immune modulatory effects revealed that <strong>2</strong> could enhance the proliferation of Jurkat T cells in a dose-dependent manner.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134851"},"PeriodicalIF":2.1,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713124","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
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