Tetrahedron最新文献

{"title":"Electrocatalytic diazidation of alkenes with modified electrodes coated by Cu nanoparticles","authors":"Xinglei He ,&nbsp;Xiaobin Zhu ,&nbsp;Luyao Wang ,&nbsp;Jingheng Li ,&nbsp;Chunlong Yu ,&nbsp;Ke-Yin Ye","doi":"10.1016/j.tet.2025.134563","DOIUrl":"10.1016/j.tet.2025.134563","url":null,"abstract":"<div><div>Vicinal diamines are an important structural motif that has been widely used in biological, medicinal, and materials science. Transition-metal-catalyzed diazidation of alkene is a straightforward and efficient approach for vicinal diamines, which are unfavorably associated with excess oxidants and limited substrate scope for electron-deficient alkenes. Herein we report an electrocatalytic diazidation of alkenes with the electrode coated by Cu nanoparticles pyrolyzed from Cu(salen)-based metal-organic framework. This strategy is compatible with various alkenes including those electro-deficient ones. Remarkably, the modified electrode maintains high electrocatalytic activity for diazidation even after 15 cycles.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134563"},"PeriodicalIF":2.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143519909","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}

{"title":"Convenient synthesis, characterization, evaluation and molecular docking of some new fused pyrazolo[3,4-d]pyrimidine derivatives and 3-methyl-8 phenylpyrazolo[3′,4':4,5]pyrimido[6,1-c][1,2,4]triazines against HeLa cancer cells","authors":"Mirna T. Helmy,&nbsp;Mohamed A. Mohamed Teleb,&nbsp;Demiana H. Hanna,&nbsp;Mohamed W. El-Maadawy,&nbsp;Hamdi M. Hassaneen,&nbsp;Monica G. Kamel","doi":"10.1016/j.tet.2025.134557","DOIUrl":"10.1016/j.tet.2025.134557","url":null,"abstract":"<div><div>Utility of the precursors 3-aryl-4-imino-1-phenylpyrazolo[3,4-<em>d</em>]pyrimidin-5-amines <strong>4a-f</strong> and 3-aryl-4-hydrazineyl-1-phenyl-1<em>H</em>-pyrazolo[3,4-<em>d</em>]pyrimidines <strong>5a-f</strong> in the synthesis of pyrazolo[3,4-<em>d</em>]pyrimidin-4-yl)hydrazono derivatives <strong>10a-l</strong> <em>via</em> reaction of the hydrazines <strong>5a-f</strong> with each of pyruvic acid or ethyl pyruvate <strong>9</strong>. Refluxing of the hydrazone derivatives <strong>10a-l</strong> in <em>N</em>,<em>N</em>-dimethylformamide for 90 h afforded the corresponding 3-methyl-8-phenylpyrazolo-[3′,4':4,5]pyrimido[6,1-<em>c</em>][1,2,4]triazine derivatives <strong>11a-f</strong>. The cytotoxic results showed that the compound <strong>11a</strong> was the most effective in suppressing the growth of HeLa cancer cells when compared to all other prepared compounds, with the most effective IC₅₀ value (3.46 ± 0.59 μg/mL) and no cytotoxic effects on normal human lung cells (WI-38). Moreover, the toxicity of the compound <strong>11a</strong> against HeLa cells was confirmed by a significant increase in LDH levels in treated HeLa cells compared to untreated ones. Using annexin V/PI, treated HeLa cells with this IC₅₀ value of compound <strong>11a</strong> displayed a considerable increase in early and late apoptotic cells in comparison to control cells. Additionally, apoptosis induction in the compound <strong>11a</strong>-treated cells was mediated through increased reactive oxygen species (ROS) production. Moreover, the compound <strong>11a</strong> markedly decreased the levels of antioxidant enzymes, including GSH, CAT, and SOD, in treated HeLa cells relative to untreated cells. Finally, the compound <strong>11a</strong> markedly raised the expression levels of cleaved caspase-3, which is the initiator of apoptosis. Overall, these findings indicate that the compound <strong>11a</strong> triggers significant cytotoxicity in HeLa cell cancer cells in a dose-dependent manner, primarily <em>via</em> ROS-mediated cell death, possibly <em>via</em> the mitochondrial pathway. So, compound <strong>11a</strong> can be used as a promising treatment option for HeLa cancer in humans. In addition, <em>in silico</em> modelling, including, bioavailability, ADMET analysis, molecular docking and molecular dynamics simulation was conducted to evaluate the drug-likeness of the novel compounds (<strong>10a-11f</strong>). Compound <strong>11a</strong> exhibited a promising binding affinity and stability against the receptors affirming its ability to act as antitumor and antioxidant ligand.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134557"},"PeriodicalIF":2.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552744","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}

{"title":"Recent advances in the syntheses and reactions of biologically promising β-lactam derivatives","authors":"Rajarshi Sarkar ,&nbsp;Dripta De Joarder ,&nbsp;Chhanda Mukhopadhyay","doi":"10.1016/j.tet.2025.134565","DOIUrl":"10.1016/j.tet.2025.134565","url":null,"abstract":"&lt;div&gt;&lt;div&gt;Beta-lactam antibiotics are among the most widely used and effective classes of antimicrobial agents in clinical medicine, and their synthesis and reactions are crucial for their continued development and optimization. The beta-lactam ring structure, characterized by a four-membered cyclic amide, is the core functional group responsible for the antimicrobial activity of these compounds. This structure is found in a variety of antibiotic classes, including penicillins, cephalosporins, monobactams, and carbapenems, which collectively represent a cornerstone in the treatment of bacterial infections. The synthesis and reactivity of beta-lactams are central to both their mechanism of action and their therapeutic efficacy, making them a focal point for ongoing research in drug design and resistance management. The synthesis of beta-lactams typically involves complex organic reactions, often requiring careful control of steric and electronic factors to ensure the correct formation of the beta-lactam ring. One key synthetic challenge is the generation of the beta-lactam ring itself, which can be achieved through various methods, including nucleophilic acylation, cyclization reactions, and enzymatic pathways. These synthetic routes must overcome significant hurdles, such as maintaining the stability of the reactive intermediate and controlling the regiochemistry of subsequent functional group additions. Advances in synthetic techniques, including the use of combinatorial chemistry, have led to the development of novel beta-lactam derivatives with improved pharmacological properties and expanded antibacterial spectra. The reactivity of beta-lactams, particularly their susceptibility to hydrolysis, plays a critical role in their mechanism of action. The beta-lactam ring undergoes nucleophilic attack by bacterial enzymes called beta-lactamases, which hydrolyze the amide bond and deactivate the antibiotic. The ability of beta-lactams to bind and inhibit bacterial cell wall synthesis, specifically the enzyme transpeptidase (also known as penicillin-binding protein, or PBP), is essential for their bactericidal activity. This interaction prevents the cross-linking of peptidoglycan, a critical component of the bacterial cell wall, leading to cell lysis and death. The reactivity of the beta-lactam ring toward PBPs is highly selective, and this specificity has made beta-lactams a valuable tool in treating infections caused by a wide range of bacterial pathogens. However, the increasing prevalence of bacterial resistance, particularly through the production of beta-lactamase enzymes, has prompted the development of beta-lactamase inhibitors and the design of new beta-lactam derivatives with enhanced stability against these enzymes. These inhibitors, such as clavulanic acid and tazobactam, act by irreversibly binding to the beta-lactamase enzyme, restoring the effectiveness of beta-lactam antibiotics. Ongoing research into the synthesis and reactivity of be","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134565"},"PeriodicalIF":2.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143534098","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}

{"title":"Reaction of acylpropargylic alcohols with 1-pyrrolines: A synthetic and quantum-chemical study","authors":"Ludmila A. Oparina,&nbsp;Anton V. Kuzmin,&nbsp;Lyudmila A. Grishchenko,&nbsp;Nikita A. Kolyvanov,&nbsp;Igor’ A. Ushakov,&nbsp;Boris A. Trofimov","doi":"10.1016/j.tet.2025.134566","DOIUrl":"10.1016/j.tet.2025.134566","url":null,"abstract":"<div><div>The reactions of acylpropargylic alcohols with 1-pyrrolines (60 °C, 2−3 h) afford the acylethenyltetrahydropyrrolo[2,1-<em>b</em>]oxazoles and furan-3(2<em>H</em>)-ylideneaminoalkanones in 55–76 % and in trace to 12 % yields, respectively. Quantum-chemical calculations (B2PLYP-D3) show that formation of pyrrolo[2,1-<em>b</em>]oxazoles is kinetically more preferable than that of furan-3(2<em>H</em>)-imines, the latter being formed through 1,3(4)-dipole and 2-hydroxypyrrolidine intermediates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134566"},"PeriodicalIF":2.1,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552741","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}

{"title":"Synthesis of benzofuro[3,2-c]quinolinones via one-pot reaction of 3-chlorooxindoles and salicylaldehydes","authors":"Feng Wang ,&nbsp;Sheng-Bin Wang ,&nbsp;Jia-Qi Pan ,&nbsp;Qiu-Yu Ma ,&nbsp;Mingshu Wu ,&nbsp;Rui Ning","doi":"10.1016/j.tet.2025.134568","DOIUrl":"10.1016/j.tet.2025.134568","url":null,"abstract":"<div><div>A mild and efficient one-pot reaction for constructing benzofuro[3,2-c]quinolinones from 3-chlorooxindoles and salicylaldehydes is presented. The method involves the base-mediated formation of a dihydrobenzofuran spirooxindole intermediate, which is subsequently converted into benzofuro[3,2-c]quinolinones facilitated by TfOH. This strategy is characterized by transition metal-free conditions, easily accessible starting materials, and a broad substrate scope.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134568"},"PeriodicalIF":2.1,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143534097","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}

{"title":"3-Fluorooxindoles from indolin-2-ones by Selectfluor","authors":"Hui Qin ,&nbsp;Guo-Liang Wei ,&nbsp;Fu-Wei Wang ,&nbsp;Xiao-Hong Mao ,&nbsp;Mei-Hua Bao ,&nbsp;Yi-Wen Zhang ,&nbsp;Ping Huang ,&nbsp;Xiao-Wei Zheng","doi":"10.1016/j.tet.2025.134556","DOIUrl":"10.1016/j.tet.2025.134556","url":null,"abstract":"<div><div>Herein, a practical and efficient method for fluorinating various indolin-2-ones under mild conditions was presented, utilizing selectfluor as a cost-effective fluorination reagent. Notably, the protocol operated under environmentally friendly conditions, facilitating the generation of various substituted indolin-2-ones into corresponding fluorinated indolin-2-ones in moderate to good yields, all without the need for an alkali source or heating.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"178 ","pages":"Article 134556"},"PeriodicalIF":2.1,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143686419","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}

{"title":"Efficient on-water synthesis of novel pyrano[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines via catalyst-free one-pot three-component reaction","authors":"Fatemeh Hamidi Dastjerdi,&nbsp;Abbas Ali Esmaeili","doi":"10.1016/j.tet.2025.134559","DOIUrl":"10.1016/j.tet.2025.134559","url":null,"abstract":"<div><div>An efficient, catalyst-free and eco-friendly synthesis of novel pyrano[3,2-<em>e</em>][1,2,4]triazolo[1,5-<em>a</em>]pyrimidines <em>via</em> cyclo-condensation of [1,2,4]triazolo[1,5-<em>a</em>]pyrimidine-5,7(4<em>H</em>,6<em>H</em>)-dione, aromatic aldehydes, and malononitrile has been described using ‘‘On-water” concept. The use of water as a clean media, catalyst-free conditions, excellent functional group acceptance, easier product isolation/purification without column chromatography, short reaction times, and good-to-excellent yields are the remarkable privileges of this protocol. Finally, ¹H, ¹³C NMR, IR, mass spectra, and elemental analyses were conducted to determine the products’ structure.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134559"},"PeriodicalIF":2.1,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143511947","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}

{"title":"A transition-metal-free 1,10-phenanthroline-promoted homocoupling reaction for the construction of biaryl diamides","authors":"Shengxing Xie,&nbsp;Jinxia Yang,&nbsp;Rong Ma,&nbsp;Minghui Liu,&nbsp;Xinyuan Zhang,&nbsp;Neng-Fei Wang,&nbsp;Chengyu Wang,&nbsp;Lingkai Kong","doi":"10.1016/j.tet.2025.134562","DOIUrl":"10.1016/j.tet.2025.134562","url":null,"abstract":"<div><div>An efficient transition-metal-free 1,10-phenanthroline-promoted homocoupling reaction has been developed to construct biaryl diamides from 2-iodobenzamides. Various desired products were smoothly synthesized with readily available starting materials in good to excellent yields under the standard reaction conditions. And this method showed a wide substrate scope and good functional group tolerance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134562"},"PeriodicalIF":2.1,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143509831","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}

{"title":"Electrochemical conversion of carboxylic acids to terminal alkenes enabled by dialkyl phosphate electrolyte","authors":"Tasuku Ito,&nbsp;Xiongjie Jin,&nbsp;Kyoko Nozaki","doi":"10.1016/j.tet.2025.134560","DOIUrl":"10.1016/j.tet.2025.134560","url":null,"abstract":"<div><div>Electrochemical regioselective conversion of carboxylic acids to terminal alkenes through dehydrogenative decarboxylation was developed. Mechanistic studies suggested that the reaction proceeds through oxidative decarboxylation of carboxylic acids to give the corresponding primary carbocation intermediates followed by deprotonation. It was implied that when using a supporting electrolyte with high donor number anion, such as dialkyl phosphate, the isomerization of the primary carbocation intermediates was suppressed to cause higher selectivity to terminal alkenes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134560"},"PeriodicalIF":2.1,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143511948","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Magnesium-mediated three-component reductive cross-couplings of aryl aldehydes, aryl bromides, and aryl 2-pyridyl esters: An efficient synthesis of diarylmethanol esters","authors":"Xiao-Wei Han ,&nbsp;Yuan-Shuai Wu ,&nbsp;Tie Wu ,&nbsp;Xue-Qiang Chu ,&nbsp;Li-Xin Zhai ,&nbsp;Chengping Miao ,&nbsp;Zhi-Liang Shen","doi":"10.1016/j.tet.2025.134558","DOIUrl":"10.1016/j.tet.2025.134558","url":null,"abstract":"<div><div>Magnesium was found to be capable of efficiently mediating the one-pot reductive cross-couplings of aryl aldehydes, aryl bromides, and pyridin-2-yl benzoates under transition metal-free conditions. The three-component reactions proceeded well at room temperature in THF in the presence of LiCl, enabling a chemoselective delivery of a large library of diarylmethanol esters in moderate to good yields with broad functionality compatibility. Apart from aryl substituted substrates which served as efficient electrophiles for the present protocol, alkyl substituted starting materials could be amenable to the reaction as well. In addition, the synthetic potency of the method is demonstrated through the scale-up synthesis and the late-stage derivatization of biologically active molecules. The method, which employed readily available starting materials and eliminated the utilization of sensitive and poorly available organometallic reagents, features simple manipulation and step-economy, potentially serving as an appealing alternative to existing methods for the access to diarylmethanol esters.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134558"},"PeriodicalIF":2.1,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143519911","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}