IF 2.2 3区化学

Tetrahedron Pub Date : 2025-10-01 DOI: 10.1016/j.tet.2025.134977

Manijeh Nematpour

引用次数: 0

Rearrangement of protected epoxy-alcohols into tetrahydrofuran derivatives: The protecting group matters! 受保护的环氧醇重排成四氢呋喃衍生物：保护基团很重要！

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-27 DOI: 10.1016/j.tet.2025.134962

Appasaheb K. Nirpal, Shyam Sathyamoorthi

{"title":"Rearrangement of protected epoxy-alcohols into tetrahydrofuran derivatives: The protecting group matters!","authors":"Appasaheb K. Nirpal, Shyam Sathyamoorthi","doi":"10.1016/j.tet.2025.134962","DOIUrl":"10.1016/j.tet.2025.134962","url":null,"abstract":"<div><div>We have explored an interesting rearrangement of protected epoxy-alcohols into tetrahydrofuran derivatives. Our protocol is operationally simple and involves treatment of a substrate with catalytic quantities of boron trifluoride diethyl etherate in methylene chloride without any special precautions to exclude air or ambient moisture. The nature of the protecting group dictates the stereochemical outcome of the cyclization. For example, with <em>trans</em>-di-substituted epoxides bearing pendant esters or carbamates, the rearrangement gives tetrahydrofurans with contiguous stereocenters in a <em>syn</em> configuration. With these substrates, we hypothesize that the transformation initiates upon attack of the epoxide by the carbonyl oxygen of the ester or carbamate. Conversely, with <em>trans</em>-di-substituted epoxides bearing free alcohols or ethers, cyclization gives tetrahydrofurans with contiguous stereocenters in an <em>anti</em> configuration. Here, we believe that a simple S<sub>N</sub>2 attack on the epoxide is taking place. We also examined the cyclization with aziridine alcohols and their derivatives and with oxetane esters and found that some of these substrates were compatible with the reaction conditions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"188 ","pages":"Article 134962"},"PeriodicalIF":2.2,"publicationDate":"2025-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145227815","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

Phenoxazinophanes: Synthesis, structure, spectral, redox and theoretical studies 苯恶唑啉类：合成、结构、光谱、氧化还原和理论研究

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134961

Neha Tripathi, Mangalampalli Ravikanth

{"title":"Phenoxazinophanes: Synthesis, structure, spectral, redox and theoretical studies","authors":"Neha Tripathi, Mangalampalli Ravikanth","doi":"10.1016/j.tet.2025.134961","DOIUrl":"10.1016/j.tet.2025.134961","url":null,"abstract":"<div><div>Three fluorescent phenoxazinophanes, each incorporating two phenoxazine units bridged by two ethene linkers, were synthesized in a three-step sequence starting from commercially available phenoxazine. Substituents such as methyl and phenyl groups were introduced at the ethene bridges for the first time, resulting in significant modulation of the electronic properties of phenoxazinophanes. The X-ray structure revealed that phenoxazine moiety in phenoxazinophane exhibits a butterfly-shaped, non-planar structure with a significant reduction in dihedral angle (36.7°) between the planes of the two benzene rings compared to the angle in free phenoxazine (167°). The spectroscopic, and electrochemical studies revealed that the properties of phenoxazinophanes markedly distinct from those of previously reported phenothiazinophanes and depends on the type of substituents present at the bridged ethene carbons. Remarkably, the phenoxazinophanes exhibit green fluorescence in the solid state with a broad emission in the region of 450–650 nm and quantum yields were in the range of 0.32–0.35. Preliminary studies indicated that phenoxazinophanes exhibit aggregation-induced emission. The electrochemical studies revealed that phenoxazinophanes are highly electron rich and DFT/TD-DFT studies were in agreement with the experimental observations.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"188 ","pages":"Article 134961"},"PeriodicalIF":2.2,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145227814","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

Paraconfuranones N–P, three new furanone polyketides with antibacterial activity from a marine-derived fungus Paraconiothyrium sporulosum DL-16 从海洋源真菌Paraconiothyrium sporulosum DL-16中提取的具有抗菌活性的三种新型呋喃酮聚酮N-P

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134952

Si-Lu Hua , Ping Liu , Xing-Chen Zhang , Li Miao , Xiao-Jian Zhou , Dongdong Wang , Wei Jiang

引用次数: 0

NHC-catalyzed higher-order (5 + 3) cyclization for accessing tetracyclic eight-membered lactones nhc催化获得四环八元内酯的高阶（5 + 3）环化反应

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134954

Ke-Xuan Tong , Shao-Qing Shi , Yin-Ping Liu, Wen-Juan Hao, Bo Jiang

引用次数: 0

Visible-light-induced synthesis of indolo/benzimidazo[2,1-a]isoquinoline derivatives via decarboxylative glycosylation 可见光诱导下脱羧糖基化合成吲哚/苯并咪唑[2,1-a]异喹啉衍生物

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134956

Xueqin Wang, Xingqin Tian, Penghua Zhang, Jing Zhang, Fang Ye, Guanghui Lv

引用次数: 0

Zampamide: A lipopeptide isolated from Caldora sp. marine cyanobacterium Zampamide：一种从Caldora sp.海洋蓝藻中分离出来的脂肽

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134953

Shunya Tojo , Kaori Ozaki , Noriyuki Natsume , Naoaki Kurisawa , Kiyotake Suenaga , Toshiaki Teruya

{"title":"Zampamide: A lipopeptide isolated from Caldora sp. marine cyanobacterium","authors":"Shunya Tojo , Kaori Ozaki , Noriyuki Natsume , Naoaki Kurisawa , Kiyotake Suenaga , Toshiaki Teruya","doi":"10.1016/j.tet.2025.134953","DOIUrl":"10.1016/j.tet.2025.134953","url":null,"abstract":"<div><div>Overweight and obesity are pathological conditions characterized by the accumulation of excessive fat. Adipokines, which are secreted by hypertrophied adipocytes, are known to increase the risk of various diseases. Therefore, identifying compounds that promote lipolysis in adipocytes is a promising way to prevent hypertrophy of these cells. Although numerous bioactive compounds have been isolated from marine cyanobacteria, reports on compounds exhibiting such activity remain limited. In this study, we report the discovery of zampamide (<strong>1</strong>), a linear lipopeptide that stimulates lipolysis in 3T3-L1 adipocytes. It was isolated from a marine cyanobacterium of the genus <em>Caldora</em> collected in Okinawa, Japan. The planar structure of <strong>1</strong> was elucidated primarily using two-dimensional NMR and mass spectrometry. The absolute configurations of the amino acid residues in <strong>1</strong> were determined after acid hydrolysis, followed by Marfey's analysis of the resulting hydrolysates. Additionally, the absolute configuration of the fatty acid moiety was determined by derivatization. Zampamide (<strong>1</strong>) increased the amount of free glycerol in a dose-dependent manner, demonstrating its lipolysis-promoting activity. These findings suggest that marine cyanobacteria are a valuable source of novel lipolysis-promoting agents for obese and overweight patients.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"188 ","pages":"Article 134953"},"PeriodicalIF":2.2,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145227817","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 cytotoxic activity of new α-pinene-based cineol-like compounds 新型α-蒎烯类桉叶酚类化合物的合成及细胞毒活性研究

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134959

Irina V. Ilyina , Oksana S. Patrusheva , Konstantin P. Volcho , Yuri V. Gatilov , Andrey A. Nefedov , Alexander Yu Sidorenko , Tatiana V. Khalimonyuk , Victoria A. Mumyatova , Maria M. Trigub , Alexei A. Terentiev , Vladimir E. Agabekov , Nariman F. Salakhutdinov

{"title":"Synthesis and cytotoxic activity of new α-pinene-based cineol-like compounds","authors":"Irina V. Ilyina , Oksana S. Patrusheva , Konstantin P. Volcho , Yuri V. Gatilov , Andrey A. Nefedov , Alexander Yu Sidorenko , Tatiana V. Khalimonyuk , Victoria A. Mumyatova , Maria M. Trigub , Alexei A. Terentiev , Vladimir E. Agabekov , Nariman F. Salakhutdinov","doi":"10.1016/j.tet.2025.134959","DOIUrl":"10.1016/j.tet.2025.134959","url":null,"abstract":"<div><div>Monoterpenes and their derivatives are often considered as widespread and cheap raw materials for the transformation into the valuable chemicals using for the development of new drugs. In this study, a series of compounds with methanofuro[3,2-<em>c</em>]pyran and methanopyrano[4,3-<em>b</em>]pyran scaffolds were synthesized starting from (+)- and (−)-α-pinene-derived monoterpenoids and <em>p</em>-halogen substituted aromatic aldehydes. These compounds contain a fragment of 1,4- and 1,8-cineoles ‒ monoterpenes exhibited a wide range of biological effects. Methanofuro[3,2-<em>c</em>]pyrans <strong>18</strong> with a fragment of 1,4-cineole were synthesized from 8-acetoxy-6-hydroxymethyllimonene in the presence of K10 dried at 105 °C in solvent-free conditions. Optimized conditions for the synthesis of the methanopyrano[4,3-<em>b</em>]pyrans <strong>19</strong> bearing the 1,8-cineol moiety were developed. It was shown that the 8-hydroxy-6-hydroxymethyllimonene reactions with aldehydes proceed with high selectivity towards product <strong>19</strong> when catalyzed by K10 (dried at 200 °C) in methylene chloride. Cytotoxic activity of cineol-like compounds was studied against HeLa, MCF7 and A-172 cells. It was shown that cytotoxic activity of compounds <strong>18b-d</strong> and <strong>19b-d</strong> is depended on both their (+)/(−) configuration and halogen atom presence in a particular structure. The most active compounds - methanopyrano[4,3-<em>b</em>]pyrans (+)-<strong>19c</strong> and (+)-<strong>19d</strong> with Cl and Br substituents exhibited high toxicity to cancerous cells, but were little toxic to Vero cells. Compounds (+)-<strong>19c</strong> and (+)-<strong>19d</strong> can exert cytostatic effects in HeLa cells or induce apoptotic cell death in MCF7 and A-172 cells.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"188 ","pages":"Article 134959"},"PeriodicalIF":2.2,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145157570","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

Bioactive scalarane-type sesterterpenoids from the Yongle Islands marine sponge Phyllospongia foliascens 永乐岛海绵叶根海绵的生物活性角鲨烷型酯萜类化合物

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-26 DOI: 10.1016/j.tet.2025.134958

Liu-Jie Chen , Gao-Ling Wu , Jie Liu , Feng-Yi Lv , Pei Yuen Ng , Qun Luo , Fan Yang , Zhi-Fan Mao , Hou-Wen Lin

{"title":"Bioactive scalarane-type sesterterpenoids from the Yongle Islands marine sponge Phyllospongia foliascens","authors":"Liu-Jie Chen , Gao-Ling Wu , Jie Liu , Feng-Yi Lv , Pei Yuen Ng , Qun Luo , Fan Yang , Zhi-Fan Mao , Hou-Wen Lin","doi":"10.1016/j.tet.2025.134958","DOIUrl":"10.1016/j.tet.2025.134958","url":null,"abstract":"<div><div>A further and systematic chemical investigation was carried out on the marine sponge <em>Phyllospongia foliascens</em>, collected from the Yongle Islands in the South China Sea, leading to the isolation of 17 scalarane-type sesterterpenoids, including five new compounds (<strong>1</strong>–<strong>5</strong>) and twelve known analogues (<strong>6</strong>–<strong>17</strong>). Their structures were determined using spectral analysis in conjunction with NMR/ECD calculations. Among the compounds, the pentacyclic sesterterpenoids <strong>3</strong> and <strong>4</strong> (featuring a 6/6/6/6/5 ring system) exhibited signal splitting in their <sup>13</sup>C NMR spectra recorded in CDCl<sub>3</sub>. This challenge was resolved by stabilizing a single configuration through NMR solvent alteration and NMR experiment temperature variation, providing a reference strategy for similar issues. Cytotoxicity evaluation using the CCK-8 assay revealed that compound <strong>3</strong> was active against both K562 and U937 cell lines (IC<sub>50</sub> = 9.00 μM and 8.45 μM, respectively), while compound <strong>4</strong> exhibited significant and selective cytotoxicity against K562 cells (IC<sub>50</sub> = 5.69 μM).</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"188 ","pages":"Article 134958"},"PeriodicalIF":2.2,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145227811","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

Facile redox synthesis of azoxyfuroxans 氮氧呋喃嘧啶的易氧化还原合成

IF 2.2 3区化学

Tetrahedron Pub Date : 2025-09-25 DOI: 10.1016/j.tet.2025.134957

Yuri A. Sidunets, Valeriya G. Melekhina, Leonid L. Fershtat

引用次数: 0

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