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Microwave-assisted one-pot synthesis of fused isoxazolo[4′,5′:3,4]pyrrolo[1,2-c]pyrimidines as potent anticancer agents: In vitro and in silico study 微波辅助一锅法合成融合异恶唑[4′，5′：3,4]吡咯[1,2-c]嘧啶的有效抗癌剂：体外和硅研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-08 DOI: 10.1016/j.tetlet.2025.155570
Raveendar Reddy Thatikonda, Karuna Sree Merugu
{"title":"Microwave-assisted one-pot synthesis of fused isoxazolo[4′,5′:3,4]pyrrolo[1,2-c]pyrimidines as potent anticancer agents: In vitro and in silico study","authors":"Raveendar Reddy Thatikonda,&nbsp;Karuna Sree Merugu","doi":"10.1016/j.tetlet.2025.155570","DOIUrl":"10.1016/j.tetlet.2025.155570","url":null,"abstract":"<div><div>Microwave-aided one-pot synthesis of certain fused isoxazolo[4′,5′:3,4]pyrrolo[1,2-<em>c</em>] pyrimidine derivatives are synthesized using one-pot Cu(I)-catalyzed [3+2]cycloaddition, followed by Pd-catalyzed C<img>C bond coupling between iodoalkyne and freshly prepared nitrile oxides in a recyclable ionic liquid [Emim]BF<sub>4</sub>. The anticancer efficacy of the synthesized isoxazoles was then tested <em>in vitro</em> against A-459 and NCI-H460 cancer cell lines, and some compounds (<strong>5k</strong>–<strong>5n</strong>) demonstrated more activity than the others, with <strong>5k</strong> and <strong>5l</strong> acting more potently than the standard drugs, 5-FU and erlotinib. We also detected EGFR inhibitory activity in the potent compounds <strong>5k</strong>, <strong>5l</strong>, <strong>5m</strong>, and <strong>5n</strong>, and the results revealed that compound <strong>5m</strong> had the highest inhibitory action compared to the other compounds and was comparable to erlotinib. We also performed <em>in silico</em> tests to assess the molecular interactions of more powerful compounds with EGFR protein (PDB: <span><span>4HJO</span><svg><path></path></svg></span>). Our findings indicated that all potent compounds had stronger binding interactions than standard erlotinib (−7.69 kcal/mol), with binding energies ranging from −8.41 to −9.26 kcal/mol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155570"},"PeriodicalIF":1.5,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791403","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
Syntheses of C22–C29 and C20–C29 sections of amphidinol 3 苯二酚3 C22-C29和C20-C29片段的合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-08 DOI: 10.1016/j.tetlet.2025.155586
Yuki Yamashita, Yuma Wakamiya, Yusuke Mita, Yoko Yasuno, Tohru Oishi
{"title":"Syntheses of C22–C29 and C20–C29 sections of amphidinol 3","authors":"Yuki Yamashita,&nbsp;Yuma Wakamiya,&nbsp;Yusuke Mita,&nbsp;Yoko Yasuno,&nbsp;Tohru Oishi","doi":"10.1016/j.tetlet.2025.155586","DOIUrl":"10.1016/j.tetlet.2025.155586","url":null,"abstract":"<div><div>Polyol segments corresponding to C22–C29 and C20–C29 sections of amphidinol 3 (AM3) were synthesized as building blocks of artificial analogues of AM3 for structure–activity relationship studies. The C22–C29 section was synthesized from (<em>S</em>)-Roche ester through continuous half-reduction of an ester and a Grignard reaction under flow and batch conditions, followed by iterative ozonolysis and Grignard reactions. The C20–C29 section was derived from the common intermediate of AM3 and the artificial analogue corresponding to the C21–C67 section via olefination and Sharpless asymmetric dihydroxylation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155586"},"PeriodicalIF":1.5,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143826258","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
Bis-dispiro-indolinone-pyrrolidine-imidazolones with polymethylene linkers between imidazolone fragments 咪唑酮片段间含聚亚甲基连接的双二吡罗-吲哚啉-吡咯烷-咪唑酮类化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-05 DOI: 10.1016/j.tetlet.2025.155589
V.S. Polyakov, E.V. Pervakova, Yu.K. Grishin, E.K. Beloglazkina
{"title":"Bis-dispiro-indolinone-pyrrolidine-imidazolones with polymethylene linkers between imidazolone fragments","authors":"V.S. Polyakov,&nbsp;E.V. Pervakova,&nbsp;Yu.K. Grishin,&nbsp;E.K. Beloglazkina","doi":"10.1016/j.tetlet.2025.155589","DOIUrl":"10.1016/j.tetlet.2025.155589","url":null,"abstract":"<div><div>A method for the synthesis of bis-(dispiro-imidazolone-pyrrolidine-indolinones) in which spirocyclic fragments are linked by C4, C6 and C8 alkyl linkers between the N(3) nitrogen atoms of the imidazolone ring has been proposed. A two-step synthetic sequence was used for the synthesis, consisting of the interaction of α,ω-dialkylamines with ethyl isothiocyanatoacetate, followed by the reaction of the intermediate bis-thioureas with substituted benzaldehydes to produce bis-arylidenetiohydantoins and the final 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatins and <em>N</em>-methylglycine.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155589"},"PeriodicalIF":1.5,"publicationDate":"2025-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143807141","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
Alkylidene transfer reactions from nitrones to iminoiodanes 烷基烯从硝基到亚胺碘的转移反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-04 DOI: 10.1016/j.tetlet.2025.155558
Noriko Okamoto, Haruto Ogino, Takuya Sueda
{"title":"Alkylidene transfer reactions from nitrones to iminoiodanes","authors":"Noriko Okamoto,&nbsp;Haruto Ogino,&nbsp;Takuya Sueda","doi":"10.1016/j.tetlet.2025.155558","DOIUrl":"10.1016/j.tetlet.2025.155558","url":null,"abstract":"<div><div>Herein, we report a reaction involving alkylidene transfer from nitrones to iminoiodanes. The alkylidene moiety is transferred from the nitrone to the imido group of the iminoiodane accompanied by cleavage of the nitrone C<img>N bond to deliver a nitroso compound and an imine. When an excess of the iminoiodane is used at higher temperature, the iminoiodane reacts with the nitroso compound to form an azoxy sulfone. We also found that an azomethine imine can be used as an alkylidene transfer agent.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155558"},"PeriodicalIF":1.5,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143768829","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
Copper(II) NHC pincer complexes containing 1,2,3-triazole units: Synthesis, structure and catalysis for CN bond forming reactions 含1,2,3-三唑单位的铜（II） NHC螯合物：合成、结构及CN成键反应的催化作用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-04 DOI: 10.1016/j.tetlet.2025.155588
Mohsen Teimouri, Mahshid Attarroshan, Bruno Donnadieu, Sean L. Stokes, Joseph P. Emerson
{"title":"Copper(II) NHC pincer complexes containing 1,2,3-triazole units: Synthesis, structure and catalysis for CN bond forming reactions","authors":"Mohsen Teimouri,&nbsp;Mahshid Attarroshan,&nbsp;Bruno Donnadieu,&nbsp;Sean L. Stokes,&nbsp;Joseph P. Emerson","doi":"10.1016/j.tetlet.2025.155588","DOIUrl":"10.1016/j.tetlet.2025.155588","url":null,"abstract":"<div><div>Two new tridentate copper(II) <em>N</em>-heterocyclic carbene (NHC) pincer complexes with triazolyl donor groups, L2, [TrzmPymBI][PF<sub>6</sub>] and L3, [bTrzmBI][PF<sub>6</sub>], were synthesized and characterized by X-ray single crystal analysis and elemental analysis. The 5-coordinate τ value shows distorted square pyramidal geometry for both complexes. These copper(II)-NHC complexes exhibited excellent catalytic activity (95–100 % conversion) for N<img>H insertion reactions toward the formation of new N<img>C bonds between aniline and methyl phenyldiazoacetate. Under optimized conditions, the catalyst was screened against 22 different aniline derivatives and achieved high conversion (65–100 %) toward both electron-donating and electron-withdrawing functional groups on the amine substrates, while limiting self-coupling of activated diazo compounds. The substrate scope study revealed that steric hindrance and basicity are key factors influencing reactivity. Secondary and aliphatic amines showed weak reactivity. Moreover, the utility of this catalyst was demonstrated through a gram-scale synthesis of a diarylhydantoin, a class of compound known to act as a COX-2 inhibitor. These results highlight the versatility and efficiency of copper(II)-NHC complexes in facilitating selective carbene insertions and provide a promising approach for the synthesis of valuable nitrogen-containing compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155588"},"PeriodicalIF":1.5,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143826250","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
Development of Fmoc-O-N(CH₃)-Bz as a novel Fmoc protecting reagent for the preparation of various Fmoc-protected amino acids. Fmoc- o - n （CH₃）-Bz作为新型Fmoc保护试剂的研制，用于制备各种Fmoc保护氨基酸。
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-03 DOI: 10.1016/j.tetlet.2025.155587
Yu Zhao, Boquan Ren, Junfeng Peng, Jiajun Chen, Feng Yang, Qing Li, Yan-Jun Xu
{"title":"Development of Fmoc-O-N(CH₃)-Bz as a novel Fmoc protecting reagent for the preparation of various Fmoc-protected amino acids.","authors":"Yu Zhao,&nbsp;Boquan Ren,&nbsp;Junfeng Peng,&nbsp;Jiajun Chen,&nbsp;Feng Yang,&nbsp;Qing Li,&nbsp;Yan-Jun Xu","doi":"10.1016/j.tetlet.2025.155587","DOIUrl":"10.1016/j.tetlet.2025.155587","url":null,"abstract":"<div><div>A novel series of Fmoc-O-N(CH₃)-sulfonyl/acyl protecting reagents was developed to overcome challenges associated with the formation of Fmoc-β-Ala-OH via the Lossen rearrangement, a limitation of commonly used Fmoc-OSu reagents. These reagents were efficiently synthesized from the cost-effective and commercially available starting material, <em>N</em>-methylhydroxylamine hydrochloride. Fmoc-O-N(CH₃)-Bz was identified as the optimal Fmoc reagent, providing the highest reaction yields under optimized mild conditions. Additionally, Fmoc-O-N(CH₃)-Bz demonstrated versatility in synthesizing a wide range of Fmoc-protected amino acids with moderate to excellent yields, with yields ranging from 70 % to 93 % for cyclic amino acids.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155587"},"PeriodicalIF":1.5,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143817380","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-component cyclization of 2-chloronitrobenzenes, sulfoxonium ylides, and elemental sulfur 2-氯硝基苯、亚砜鎓化物和单质硫的三组分环化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-01 DOI: 10.1016/j.tetlet.2025.155574
Hoang V.M. Trinh , Vu H. Luu , Kien Q. Truong , Khoa H.D. Nguyen , Tuong Q. Le , Tung T. Nguyen , Duyen K. Nguyen
{"title":"Three-component cyclization of 2-chloronitrobenzenes, sulfoxonium ylides, and elemental sulfur","authors":"Hoang V.M. Trinh ,&nbsp;Vu H. Luu ,&nbsp;Kien Q. Truong ,&nbsp;Khoa H.D. Nguyen ,&nbsp;Tuong Q. Le ,&nbsp;Tung T. Nguyen ,&nbsp;Duyen K. Nguyen","doi":"10.1016/j.tetlet.2025.155574","DOIUrl":"10.1016/j.tetlet.2025.155574","url":null,"abstract":"<div><div>Synthesis of 2-acyl benzothiazoles from substituted nitroarenes as the starting material is rare. Herein we report a method to allow for the coupling of 2-chloronitrobenzene derivatives, substituted sulfoxonium ylides, and elemental sulfur to afford 2-acyl benzothiazoles. Studies regarding scope of functionalities revealed that protected phenol, dimethylamino, and heterocycles groups could be tolerated. That both aryl and alkyl sulfoxonium ylides were competent substrates overcome the current limitation in yielding 2-acyl benzothiazoles from 2-halonitroarenes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155574"},"PeriodicalIF":1.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791445","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
Thermohexins A and B, two new hexacyclicpeptides from marine algae-derived Streptomyces thermolineatus NAK03196 热己肽A和B是两种从海藻衍生的热链霉菌（Streptomyces thermomolineatus） NAK03196中获得的新六环肽
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-01 DOI: 10.1016/j.tetlet.2025.155565
Guo Dong Zhang , Cheng Yuan Yuan , Ling Jiao Zou, Bo Zhang, Rui Hua Jiao
{"title":"Thermohexins A and B, two new hexacyclicpeptides from marine algae-derived Streptomyces thermolineatus NAK03196","authors":"Guo Dong Zhang ,&nbsp;Cheng Yuan Yuan ,&nbsp;Ling Jiao Zou,&nbsp;Bo Zhang,&nbsp;Rui Hua Jiao","doi":"10.1016/j.tetlet.2025.155565","DOIUrl":"10.1016/j.tetlet.2025.155565","url":null,"abstract":"<div><div>This study describes the isolation and structural elucidation of two new hexacyclic peptides, thermohexins A (<strong>1</strong>) and B (<strong>2</strong>), from the fermentation broth of the marine algae-associated bacterium <em>Streptomyces thermolineatus</em> NAK03196. Their structures were determined using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), tandem mass spectrometry (MS/MS), nuclear magnetic resonance (NMR) spectroscopy, and the modified Marfey's method. Genomic analysis revealed that tyrohexins are biosynthesized via a nonribosomal peptide synthetase (NRPS) pathway and undergo macrocyclization mediated by a penicillin-binding protein-like thioesterase.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155565"},"PeriodicalIF":1.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143739084","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 (±)-sumatranin C （±）-苏门答腊素C的全合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-31 DOI: 10.1016/j.tetlet.2025.155561
Zen Suzuki, Yuichiro Kawamoto, Toyoharu Kobayashi, Hisanaka Ito
{"title":"Total synthesis of (±)-sumatranin C","authors":"Zen Suzuki,&nbsp;Yuichiro Kawamoto,&nbsp;Toyoharu Kobayashi,&nbsp;Hisanaka Ito","doi":"10.1016/j.tetlet.2025.155561","DOIUrl":"10.1016/j.tetlet.2025.155561","url":null,"abstract":"<div><div>The first total synthesis of (±)-sumatranin C was accomplished. The synthesis features an intermolecular aldol reaction to connect two parts of the molecule and an acid-induced acetal cyclization to form the tricyclic framework. The present strategy would be applicable to synthesize other related natural products.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155561"},"PeriodicalIF":1.5,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143739162","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 reactivity of 4-N-alkylpyridiniumyl/4-N-alkylquinoliniumyl diazoalkanes 4- n -烷基吡啶酰/4- n -烷基喹啉酰重氮烷烃的合成及反应性
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-31 DOI: 10.1016/j.tetlet.2025.155547
Cheng-Xi Li, Yi Li, Zeng-Feng Li, Ya-Xi Li, Yuan Tian, Mei-Hua Shen, Hua-Dong Xu
{"title":"Synthesis and reactivity of 4-N-alkylpyridiniumyl/4-N-alkylquinoliniumyl diazoalkanes","authors":"Cheng-Xi Li,&nbsp;Yi Li,&nbsp;Zeng-Feng Li,&nbsp;Ya-Xi Li,&nbsp;Yuan Tian,&nbsp;Mei-Hua Shen,&nbsp;Hua-Dong Xu","doi":"10.1016/j.tetlet.2025.155547","DOIUrl":"10.1016/j.tetlet.2025.155547","url":null,"abstract":"<div><div>4-(diazoalkyl)-1-alkylpyridinium and 4-(diazoalkyl)-1-alkylquinolinium salts are made from corresponding pyridinyl and quinolinyl diazoalkanes via direct N-alkylation with appropriate alkylating reagent. These novel diazoalkanes show enhanced thermal and chemical stabilities than their precursors. They can undergo [3 + 2] cycloaddition reaction and transition metal catalyzed carbenoid transformations.</div><div>2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155547"},"PeriodicalIF":1.5,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143785165","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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