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Three new alkaloids from Corydalis saxicola and their antiproliferative activity
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-22 DOI: 10.1016/j.tetlet.2025.155513
Mei-Shan Li , Li Luo , Gang Wei , Xi-Xi Song , Hai-Ying Luo , Heng-Shan Wang , Jia-Zi Luo
{"title":"Three new alkaloids from Corydalis saxicola and their antiproliferative activity","authors":"Mei-Shan Li ,&nbsp;Li Luo ,&nbsp;Gang Wei ,&nbsp;Xi-Xi Song ,&nbsp;Hai-Ying Luo ,&nbsp;Heng-Shan Wang ,&nbsp;Jia-Zi Luo","doi":"10.1016/j.tetlet.2025.155513","DOIUrl":"10.1016/j.tetlet.2025.155513","url":null,"abstract":"<div><div>Three undescribed protoberberine alkaloids, named corydalisine L-N, along with four known compounds, were isolated from <em>Corydalis saxicola</em>. Their structures were accurately characterized using nuclear magnetic resonance (NMR) and mass spectrometry (MS). The absolute configurations were determined through the calculation of electronic circular dichroism (ECD). Compounds 1–3 were relatively rare 8,13-dicarbonyl protoberbine alkaloids, which are uncommon in plants of the genus Corydalis. All compounds were evaluated for their cytotoxicity against four human cancer cell lines.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155513"},"PeriodicalIF":1.5,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 antibacterial applications of Gemini-QA N-chloramines with rigid spacer
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-21 DOI: 10.1016/j.tetlet.2025.155512
Lingdong Li, Weilun Zhang, Pengfei Liu, Suyuan Liu, Zhongtian Du, Hao Zhou
{"title":"Synthesis and antibacterial applications of Gemini-QA N-chloramines with rigid spacer","authors":"Lingdong Li,&nbsp;Weilun Zhang,&nbsp;Pengfei Liu,&nbsp;Suyuan Liu,&nbsp;Zhongtian Du,&nbsp;Hao Zhou","doi":"10.1016/j.tetlet.2025.155512","DOIUrl":"10.1016/j.tetlet.2025.155512","url":null,"abstract":"<div><div>Starting from piperazine and diazabicyclooctane respectively, two series of Gemini-quaternary ammonium (QA) <em>N</em>-chloramines <strong>6–9</strong> and <strong>10–13</strong> were synthesized with rigid spacer embedded via ploy-step synthesis strategy. Preliminary antibacterial data showed that “team effort” biocidal effect was observed for resultant <em>N</em>-chloramines, and <strong>6</strong> exhibited superior antibacterial efficacy in contrast with <strong>10</strong>. In addition, the linker length plays a decisive role in biocidal performance and <strong>9</strong>/<strong>13</strong> (linker as -(CH<sub>2</sub>)<sub>10</sub>-) achieved the highest efficacy. Our results may inspire exploration of new generation of <em>N</em>-chloramine biocides with more potent bactericidal activity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155512"},"PeriodicalIF":1.5,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143520424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-20 DOI: 10.1016/j.tetlet.2025.155507
Ilia Perov, Karizza F. Catenza, Jose Jr. Abucay, Yu-Ting Hsiao, John C. Vederas
{"title":"Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids","authors":"Ilia Perov,&nbsp;Karizza F. Catenza,&nbsp;Jose Jr. Abucay,&nbsp;Yu-Ting Hsiao,&nbsp;John C. Vederas","doi":"10.1016/j.tetlet.2025.155507","DOIUrl":"10.1016/j.tetlet.2025.155507","url":null,"abstract":"<div><div>Four decarboxylative conjugate radical addition methods, including recent and greener methods using Fe- and Eosin Y as photocatalysts, were examined using Seebach-Beckwith dehydroalanine as a radical acceptor. Head-to-head comparison of yields and purity suggests that Ir-photocatalyzed decarboxylation of carboxylic acids is the optimal method for syntheses involving resonance-stabilized radicals. However, approaches relying on cheaper Ni-, Fe-, and Eosin Y-catalyzed processes are quite viable for the conjugate addition of 1°, 2°, and 3° radicals.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155507"},"PeriodicalIF":1.5,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507959","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Vicinal diphosphorylation of enaminones with diaryl phosphine oxides via AlCl3-mediated CN bond cleavage
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-20 DOI: 10.1016/j.tetlet.2025.155472
Xin Jin , Yong An , Jia Chen , Xianheng Wang , Huabin Wang , Changkuo Zhao , Qiang Huang
{"title":"Vicinal diphosphorylation of enaminones with diaryl phosphine oxides via AlCl3-mediated CN bond cleavage","authors":"Xin Jin ,&nbsp;Yong An ,&nbsp;Jia Chen ,&nbsp;Xianheng Wang ,&nbsp;Huabin Wang ,&nbsp;Changkuo Zhao ,&nbsp;Qiang Huang","doi":"10.1016/j.tetlet.2025.155472","DOIUrl":"10.1016/j.tetlet.2025.155472","url":null,"abstract":"<div><div>A vicinal diphosphorylation of enaminones with diaryl phosphine oxides have been established condition through AlCl<sub>3</sub> as Lewis acid in this work. The transformation features excellent functional group tolerance, operational simplicity, and high yields, which provides an alternative strategy for accessing various diphosphoryl products <strong>3a</strong>. Preliminary mechanism studies suggest the conversion between <strong>1a</strong> and <strong>2a</strong> involves the elimination of dimethylamine and cascade vicinal addition. This research provides significant value to the vicinal functionalization of enaminones.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155472"},"PeriodicalIF":1.5,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143445859","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Post-Ugi cyclization approach for transition metal-free synthesis of Azetidine derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-18 DOI: 10.1016/j.tetlet.2025.155509
Rozita Yazzaf , Mohammad Hosein Sayahi , Mohammad Mahdavi
{"title":"Post-Ugi cyclization approach for transition metal-free synthesis of Azetidine derivatives","authors":"Rozita Yazzaf ,&nbsp;Mohammad Hosein Sayahi ,&nbsp;Mohammad Mahdavi","doi":"10.1016/j.tetlet.2025.155509","DOIUrl":"10.1016/j.tetlet.2025.155509","url":null,"abstract":"<div><div>A novel, metal-free strategy has been developed for the efficient synthesis of unique azetidine derivatives via a post-Ugi cyclization. This method involves generating 4-component Ugi adducts by reacting aldehydes, isocyanides, primary propargylamine, and 2-(phenylamino) benzoic acid. In the subsequent post-Ugi cyclization, azetidine derivatives are synthesized through a nucleophilic attack of a carbanion on the alkyne, followed by an intramolecular cyclization that forms a new carbon‑carbon bond.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155509"},"PeriodicalIF":1.5,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143437737","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Stabilization and structure elucidation of unstable Corynoxine-type stereoisomers using tartaric acid
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-18 DOI: 10.1016/j.tetlet.2025.155510
Yuta Koseki , Ryosuke Sugiyama , Soichiro Nishimura , Takako Sugahara , Ryuji Asano , Mami Yamazaki , Katsuyuki Aoki
{"title":"Stabilization and structure elucidation of unstable Corynoxine-type stereoisomers using tartaric acid","authors":"Yuta Koseki ,&nbsp;Ryosuke Sugiyama ,&nbsp;Soichiro Nishimura ,&nbsp;Takako Sugahara ,&nbsp;Ryuji Asano ,&nbsp;Mami Yamazaki ,&nbsp;Katsuyuki Aoki","doi":"10.1016/j.tetlet.2025.155510","DOIUrl":"10.1016/j.tetlet.2025.155510","url":null,"abstract":"<div><div>In oxindole alkaloids, stereoisomer formation occurs via bond cleavage at the spiro carbon center, followed by an intramolecular Mannich reaction. Since the possible common transition state possesses two prochiral faces, four stereoisomers at the C-3 and C-7 positions are potentially generated; however, few have been reported in nature. In this study, the four corynoxine stereoisomers were isolated, and their structures were elucidated. Two of these stereoisomers were found to be structurally unstable. Addtion of tartaric acid as a chemical trap reagent stabilized these isomers named corynoxines C and D and revealed their stereochemistries as 3<em>R</em>, 7<em>S</em> and 3<em>R</em>, 7<em>R</em>, respectively.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155510"},"PeriodicalIF":1.5,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143437736","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Visible-light promoted radical coupling of difluoroenol silyl ethers and difluorinated Pyf-sulfides to construct tetrafluoroethylene-containing compounds
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-16 DOI: 10.1016/j.tetlet.2025.155505
Chen Wang , Zhihua Wang , Jinliang Zhang , Miaomiao Mu , Jin Zhang , Zhiming Wang , Jianguo Yang , Guobo Huang , Xiaolei Zhu
{"title":"Visible-light promoted radical coupling of difluoroenol silyl ethers and difluorinated Pyf-sulfides to construct tetrafluoroethylene-containing compounds","authors":"Chen Wang ,&nbsp;Zhihua Wang ,&nbsp;Jinliang Zhang ,&nbsp;Miaomiao Mu ,&nbsp;Jin Zhang ,&nbsp;Zhiming Wang ,&nbsp;Jianguo Yang ,&nbsp;Guobo Huang ,&nbsp;Xiaolei Zhu","doi":"10.1016/j.tetlet.2025.155505","DOIUrl":"10.1016/j.tetlet.2025.155505","url":null,"abstract":"<div><div>A visible-light promoted radical coupling of difluoroenol silyl ethers and difluorinated Pyf-sulfides has been developed. This protocol provides a simple and straightforward approach to assemble diverse functionalized tetrafluoroethylene-containing compounds in moderate to good yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155505"},"PeriodicalIF":1.5,"publicationDate":"2025-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143511826","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Total synthesis of collagen crosslinker deoxypyridinoline
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-14 DOI: 10.1016/j.tetlet.2025.155508
Hiroaki Ishii, Ryosuke Shigeta, Kaho Oishi, Toyonobu Usuki
{"title":"Total synthesis of collagen crosslinker deoxypyridinoline","authors":"Hiroaki Ishii,&nbsp;Ryosuke Shigeta,&nbsp;Kaho Oishi,&nbsp;Toyonobu Usuki","doi":"10.1016/j.tetlet.2025.155508","DOIUrl":"10.1016/j.tetlet.2025.155508","url":null,"abstract":"<div><div>Collagen, a fibrous protein, accounts for 30 % of all proteins in the human body and serves as an essential extracellular matrix component that imparts mechanical strength to connective tissues such as skin and bones. Deoxypyridinoline, a collagen crosslinking amino acid, was first isolated from bovine bone in 1982. This compound is released into the bloodstream during bone resorption without being reused and has recently garnered attention as a biomarker for osteoporosis. In this study, we achieved the total synthesis of deoxypyridinoline, with a 22 % overall yield, in five steps from commercially available protected amino acids. The synthesis would aid a quantitative analysis of deoxypyridinoline as an alternative to isolating it from natural sources.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155508"},"PeriodicalIF":1.5,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143511827","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Three unusual 4-oxo-20-nor-taxanes from the cell cultures of Taxus × media
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-13 DOI: 10.1016/j.tetlet.2025.155503
Yuxin Wang , Changkang Li , Songyang Sui, Jimei Liu, Jungui Dai
{"title":"Three unusual 4-oxo-20-nor-taxanes from the cell cultures of Taxus × media","authors":"Yuxin Wang ,&nbsp;Changkang Li ,&nbsp;Songyang Sui,&nbsp;Jimei Liu,&nbsp;Jungui Dai","doi":"10.1016/j.tetlet.2025.155503","DOIUrl":"10.1016/j.tetlet.2025.155503","url":null,"abstract":"<div><div>Mediataxanes A–C (<strong>1</strong>–<strong>3</strong>), three unusual 4-oxo-20-<em>nor</em>-taxanes with 6/8/6 ring system were isolated from <em>Taxus × media</em> cell cultures. Their structures were determined by extensive spectroscopic data, and the absolute configurations were confirmed by X-ray crystallographic analysis (<strong>1</strong> and <strong>2</strong>) and NMR data comparison (<strong>3</strong>). Biological assay revealed that <strong>1</strong> exhibited moderate cytotoxicity against gastric carcinoma BGC823 and cervical cancer HeLa cells. In addition, a plausible mechanism for the oxidative cleavage of 4(20)-exocyclic-double bond and the formation of 4-carbonyl group in <strong>1</strong>–<strong>3</strong> is proposed.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155503"},"PeriodicalIF":1.5,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143395967","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-08 DOI: 10.1016/j.tetlet.2025.155504
Lucas Martins Correa Böhs , Calebe Hebrom Livistom Silva , Natália Emanuele Biolosor Kuntz , Benhur Godoi , Andrielli Leitemberger , Marcelo Godoi
{"title":"A sustainable approach for the bis-selenylation of alkynes: Design, synthesis and mechanistic studies","authors":"Lucas Martins Correa Böhs ,&nbsp;Calebe Hebrom Livistom Silva ,&nbsp;Natália Emanuele Biolosor Kuntz ,&nbsp;Benhur Godoi ,&nbsp;Andrielli Leitemberger ,&nbsp;Marcelo Godoi","doi":"10.1016/j.tetlet.2025.155504","DOIUrl":"10.1016/j.tetlet.2025.155504","url":null,"abstract":"<div><div>Herein we report an efficient and eco-friendly methodology for the selective synthesis of 1,2-<em>bis</em>-organylselanyl alkenes from diorganyl diselenides and terminal alkynes. In this regard, the use of the water extract of rice straw ash (<em>WERSA</em>) proved to be an efficient reaction media promoting the synthesis of the desired compounds in up to 97 % yield with reasonable stereoselectivity. Furthermore, the combination of experimental studies and DFT calculations enabled us to propose a plausible reaction pathway.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155504"},"PeriodicalIF":1.5,"publicationDate":"2025-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143420360","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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