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Convenient synthesis of highly functionalized isoxazoles including an amidine skeleton based on trichloroacetamidine, alkynes, and hydroxyimidoyl chloride 以三氯乙脒、炔烃和羟基酰氯为基础的高功能化异恶唑的便捷合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155443
Manijeh Nematpour
{"title":"Convenient synthesis of highly functionalized isoxazoles including an amidine skeleton based on trichloroacetamidine, alkynes, and hydroxyimidoyl chloride","authors":"Manijeh Nematpour","doi":"10.1016/j.tetlet.2024.155443","DOIUrl":"10.1016/j.tetlet.2024.155443","url":null,"abstract":"<div><div>The synthesis of functionalized isoxazole-4-carboximidamide with appropriate yields through a novel four-component reaction from alkynes, hydroxyimidoyl chloride, trichloroacetonitrile, and various amines is a remarkable achievement in heterocycle chemistry. This strategy offers a direct and efficient route to access different isoxazoles with amidine substitution from readily available starting materials. The use of copper (I) as a catalyst, without adding ligand, in THF solvent, and with the help of ultrasonic conditions for 45 min at room temperature highlights the importance of transition metal catalysis in this process.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155443"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159670","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
Enzymatic synthesis and characterization of nicotinamide riboside pseudouridine diphosphate 烟酰胺核苷假尿苷二磷酸的酶合成与表征
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155432
Yinghan Hu , Xueying Wang , Yanzhe Huang , Xiaojia Guo , Haizhao Xue , Martin Pfeiffer , Bernd Nidetzky , Zongbao K. Zhao
{"title":"Enzymatic synthesis and characterization of nicotinamide riboside pseudouridine diphosphate","authors":"Yinghan Hu ,&nbsp;Xueying Wang ,&nbsp;Yanzhe Huang ,&nbsp;Xiaojia Guo ,&nbsp;Haizhao Xue ,&nbsp;Martin Pfeiffer ,&nbsp;Bernd Nidetzky ,&nbsp;Zongbao K. Zhao","doi":"10.1016/j.tetlet.2024.155432","DOIUrl":"10.1016/j.tetlet.2024.155432","url":null,"abstract":"<div><div>Nicotinamide adenine dinucleotide (NAD) analogs are of great interests for chemical and biological applications. In this work, a novel NAD analog, nicotinamide riboside pseudouridine diphosphate (NpUD) was synthesized via coupling of pseudouridine triphosphate and nicotinamide mononucleotide catalyzed by a mutant of nicotinic acid mononucleotide adenylyltransferase. It was found that NpUD is more stable than NAD against a common pyrophosphatase NudC found in <em>Escherichia coli</em>. Interestingly, NpUD could function as redox cofactor for several oxidoreductases, among them a mutant methanol dehydrogenase showed 1.9-fold higher activity with NpUD than that with NAD. Overall, the results offer opportunities to explore NpUD in other applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155432"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159577","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
Regioselective synthesis of quaternized cellulose nanocrystals and its antibacterial properties in clinical isolates of methicillin-resistant Staphylococcus aureus 季铵化纤维素纳米晶的区域选择性合成及其对耐甲氧西林金黄色葡萄球菌临床分离株的抗菌性能
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155420
Nadarajah Vasanthan, Dong Kwon, Steven Furman
{"title":"Regioselective synthesis of quaternized cellulose nanocrystals and its antibacterial properties in clinical isolates of methicillin-resistant Staphylococcus aureus","authors":"Nadarajah Vasanthan,&nbsp;Dong Kwon,&nbsp;Steven Furman","doi":"10.1016/j.tetlet.2024.155420","DOIUrl":"10.1016/j.tetlet.2024.155420","url":null,"abstract":"<div><div>Quaternized cellulose nanocrystals (CNCs) were prepared by chloroacetylation and subsequent reaction with tertiary amines. The chloroacetylation of CNCs and quaternary ammonium-modified CNCs were characterized by the analysis of FTIR and solid-state NMR spectroscopies. Chloroacetylation of CNCs was found to be highly regioselective. CNCs can be chemically modified to tailor their properties to improve dispersion in the polymer matrix, which expands the application of CNCs as reinforcing materials. Biological evaluation of the ammonium-modified compounds was conducted using the disc diffusion test, minimum bactericidal concentration, and bacterial killing pattern for methicillin-associated multidrug-resistant clinical isolates of <em>Staphylococcus aureus</em>, one of the most problematic bacterial human pathogens. Results showed that the CNC with alkyl chains with 16 carbons had more antibacterial properties than that of 10 carbons against all tested clinical isolates of <em>Staphylococcus aureus</em> regardless of antibiotic resistance or sensitivity. This finding suggests that the ammonium-modified CNCs may be applicable to treat <em>Staphylococcus aureus</em> infections.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155420"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159579","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
Asymmetric one-pot synthesis of trans-stilbene oxide via desymmetrizing monosulfonylation of meso-hydrobenzoin catalyzed by a chiral bisoxazoline–copper (II) complex 手性双恶唑-铜（II）配合物催化中羟基苯甲酸反对称单磺化一锅法合成反式二苯乙烯氧化物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155435
Kenji Yatsuzuka, Midori Kawasaki, Ryuichi Shirai
{"title":"Asymmetric one-pot synthesis of trans-stilbene oxide via desymmetrizing monosulfonylation of meso-hydrobenzoin catalyzed by a chiral bisoxazoline–copper (II) complex","authors":"Kenji Yatsuzuka,&nbsp;Midori Kawasaki,&nbsp;Ryuichi Shirai","doi":"10.1016/j.tetlet.2024.155435","DOIUrl":"10.1016/j.tetlet.2024.155435","url":null,"abstract":"<div><div>Chiral stilbene oxides are useful and versatile intermediates for the synthesis of chiral ligands for asymmetric catalysis, chiral auxiliaries for diastereoselective transformations, and precursors for chiral building blocks of many compounds. We achieved the enantioselective desymmetric tosylation of <em>meso</em>-hydrobenzoin catalyzed by a chiral ligand–CuCl<sub>2</sub> complex followed by base promoted intramolecular cyclization to furnish <em>trans</em>-stilbene oxide in high yield with excellent enantioselectivity up to 99 %ee in a one-pot operation. This simple transformation offers the most feasible and promising option for the asymmetric synthesis of stilbene oxides with high optical purity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155435"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159575","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
Unified synthesis of DSPC and PSPC: Chemical entities of hydrogenated soy L-α-phosphatidylcholine (HSPC), a key component of liposomal drug formulations DSPC和PSPC的统一合成：氢化大豆L-α-磷脂酰胆碱（HSPC）的化学实体，是脂质体药物制剂的关键成分
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155424
Pallavi Rao, Madhavachary Rudrakshula, Rajendar Potham, Rahul Varma Katari, Vishnuvardhana Vema Reddy Eda, Saikat Sen, Srinivas Oruganti
{"title":"Unified synthesis of DSPC and PSPC: Chemical entities of hydrogenated soy L-α-phosphatidylcholine (HSPC), a key component of liposomal drug formulations","authors":"Pallavi Rao,&nbsp;Madhavachary Rudrakshula,&nbsp;Rajendar Potham,&nbsp;Rahul Varma Katari,&nbsp;Vishnuvardhana Vema Reddy Eda,&nbsp;Saikat Sen,&nbsp;Srinivas Oruganti","doi":"10.1016/j.tetlet.2024.155424","DOIUrl":"10.1016/j.tetlet.2024.155424","url":null,"abstract":"<div><div>A simple, unified and scalable strategy, emanating from the readily available chiral pool <span>d</span>-solketal, has been employed to obtain the enantiomerically pure components of hydrogenated soy L-α-phosphatidylcholine (HSPC), namely distearoyl phosphatidylcholine (DSPC) and 1-palmitoyl-2-stearoyl-phosphatidylcholine (PSPC). HSPC is obtained by hydrogenating naturally occurring soy L-α-lecithin; this affords a glycerophospholipid mixture containing C-16 (minor) or C-18 (major) fatty acid chain at <em>sn</em>-1, C-18 chain at <em>sn</em>-2 position and phosphatidylcholine at <em>sn</em>-3 position. HSPC already has numerous applications as an excipient and essential component in many FDA approved liposomal drug formulations such as Doxil® (doxorubicin HCl liposome injection) and AmBisome® (amphotericin B liposome injection). However, there is increasing interest in uncovering the potential individual applications of its components, DSPC and PSPC, too. In this context, the current synthesis offers a strategy to have a ready bespoke access to multi-gram quantities of DSPC and PSPC (in particular) that does not rely on tedious separation of the components of HSPC.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155424"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159666","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
O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species 羟基吡啶及其衍生物的瞬态烷基重氮氧烷基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155396
Guillaume Reynard , Calvine Lai , Emna Azek , Hélène Lebel
{"title":"O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species","authors":"Guillaume Reynard ,&nbsp;Calvine Lai ,&nbsp;Emna Azek ,&nbsp;Hélène Lebel","doi":"10.1016/j.tetlet.2024.155396","DOIUrl":"10.1016/j.tetlet.2024.155396","url":null,"abstract":"<div><div>Diazotisation of amines with a nitrite reagent was performed in the presence of hydroxy-pyridines and derivatives to give the alkylation products. The <em>O</em>-alkylation product was isolated from 2-, 3-, 4-hydroxypyridines, 2-hydroxyquinoline and 2-hydroxypyrimidines. In the case of 2-hydropyridines, the <em>N</em>-alkylation product was also observed, with the <em>O</em>-alkylation product being favoured. The reaction conditions were compatible with a variety of functional groups, and namely amino alcohols were successfully reacted to afford hydroxy-substituted products. The distinctive reactivity of dinitrites in comparison to mononitrites is also addressed.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155396"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160319","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
Facile and diverse synthesis of indolyl substituted 4,5,6,7-tetrahydro-4H-indol-4-ones and 1,6-dihydropyrrolo[2,3-c]pyrazol via multi-component reactions 多组分反应合成吲哚取代4,5,6,7-四氢- 4h -吲哚-4-酮和1,6-二氢吡咯[2,3-c]吡唑的简便多样
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155444
Jing Wang , Lu Yu , Haoqiang Jiang , Songlei Zhu
{"title":"Facile and diverse synthesis of indolyl substituted 4,5,6,7-tetrahydro-4H-indol-4-ones and 1,6-dihydropyrrolo[2,3-c]pyrazol via multi-component reactions","authors":"Jing Wang ,&nbsp;Lu Yu ,&nbsp;Haoqiang Jiang ,&nbsp;Songlei Zhu","doi":"10.1016/j.tetlet.2024.155444","DOIUrl":"10.1016/j.tetlet.2024.155444","url":null,"abstract":"<div><div>An efficient and facile protocol for the synthesis of some novel 4,5,6,7-tetrahydro-4H-indol-4-ones, 1,6-dihydropyrrolo[2,3-<em>c</em>]pyrazol and 1,4-dihydrochromeno [4,3-<em>b</em>]pyrrol by one-pot three-component reaction of 3-cyanoacetyl indoles, arylglyoxal monohydrate and various enaminones, pyrazol-5-amines or 4-amino coumarin. The advantages of this method include the availability of starting materials, mild reaction conditions and good yields of products, operational simplicity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155444"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159574","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
Hydroarylative cyclization of enynes with aromatic ketones catalyzed by a low-valent iron-phosphine complex 低价铁膦配合物催化炔与芳香酮的芳基化环化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155409
Yoichi Kitazawa , Takuya Kochi , Fumitoshi Kakiuchi
{"title":"Hydroarylative cyclization of enynes with aromatic ketones catalyzed by a low-valent iron-phosphine complex","authors":"Yoichi Kitazawa ,&nbsp;Takuya Kochi ,&nbsp;Fumitoshi Kakiuchi","doi":"10.1016/j.tetlet.2024.155409","DOIUrl":"10.1016/j.tetlet.2024.155409","url":null,"abstract":"<div><div>We report here an iron-catalyzed C<img>H functionalization of aromatic ketones via cyclization of enynes. The reaction is applicable to a variety of aromatic ketones and enables regioselective introduction of a hydrogen atom and an aryl group at the alkyne moiety and the olefin moiety, respectively.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155409"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143127949","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
Ambient temperature activation of diaryliodonium salts: Atom-economic route towards the ex-situ metal-free synthesis of N-methyldiarylamine 二芳基碘鎓盐的室温活化：n -甲基二芳胺非原位合成的原子经济途径
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155436
Dhanashri A. Sable, Anant R. Kapdi
{"title":"Ambient temperature activation of diaryliodonium salts: Atom-economic route towards the ex-situ metal-free synthesis of N-methyldiarylamine","authors":"Dhanashri A. Sable,&nbsp;Anant R. Kapdi","doi":"10.1016/j.tetlet.2024.155436","DOIUrl":"10.1016/j.tetlet.2024.155436","url":null,"abstract":"<div><div>An atom economic route for the synthesis of <em>N</em>-methylarylamines via the ambient temperature activation of diaryliodonium salts using an ex-situ generated HNMe<sub>2</sub> has been disclosed and a scale-up reaction was also performed to demonstrate the scalability of the developed protocol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155436"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159576","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
Silver-catalyzed regioselective synthesis of (E)-vinyl sulfones from nitroolefins and thiophenols 银催化区域选择性合成(E)-乙烯基砜的硝基烯烃和噻吩
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155425
Kaiyang Zhou , Xinyi Wang , Can Wang , Yunfeng Chen
{"title":"Silver-catalyzed regioselective synthesis of (E)-vinyl sulfones from nitroolefins and thiophenols","authors":"Kaiyang Zhou ,&nbsp;Xinyi Wang ,&nbsp;Can Wang ,&nbsp;Yunfeng Chen","doi":"10.1016/j.tetlet.2024.155425","DOIUrl":"10.1016/j.tetlet.2024.155425","url":null,"abstract":"<div><div>An efficient silver-catalyzed synthesis of (<em>E</em>)-vinyl sulfones was developed by denitrative radical cross-coupling of readily available thiophenols and nitroolefins. This reaction is initiated by generation of a thiyl radical or a sulfonyl radical from the thiophenol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155425"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159586","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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