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Catalyst-free synthesis of new hydrazino thiazole derivatives in water under ultrasonication and evaluation of their antioxidant activity 超声条件下在水中无催化剂合成新的肼基噻唑衍生物并评估其抗氧化活性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-06 DOI: 10.1016/j.tet.2024.134227
{"title":"Catalyst-free synthesis of new hydrazino thiazole derivatives in water under ultrasonication and evaluation of their antioxidant activity","authors":"","doi":"10.1016/j.tet.2024.134227","DOIUrl":"10.1016/j.tet.2024.134227","url":null,"abstract":"<div><p>An active approach for the preparation of a series of novel 3-[2ʹ-(4ʹ-aryl-1,3-thiazol-2ʹ-yl) hydrazono]indoline-2-one derivatives <strong>(4)</strong> has been executed by a one-pot multicomponent reaction of differently substituted isatins, hydrazinecarbothioamide and aracyl bromides under catalyst-free ultrasonication. This organic conversion occurs efficiently in an aqueous medium, illustrating a massive functional group tolerance. The method is <em>green</em> and the products are obtained in excellent yield in very short durations. On top of this, the reaction process does not demand for chromatographic purification and this procedure has the potency for extensive utilisation in drug companies. The test compounds <strong>4i</strong> and <strong>6</strong> revealed extremely good antioxidant behaviour with IC<sub>50</sub> values of 5.02 and 8.54 μg/mL respectively. Additionally, <em>In-silico</em> ADME and bioavailability radar study suggests that the compounds <strong>4i</strong> and <strong>6</strong> may be utilized as oral drugs and in the intravenous therapy.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142274897","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
Bioactivity and application of phenoxazines with different mitochondria-targeted lipophilic cationic groups 具有不同线粒体靶向亲脂阳离子基团的吩噁嗪的生物活性及其应用
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-05 DOI: 10.1016/j.tet.2024.134228
{"title":"Bioactivity and application of phenoxazines with different mitochondria-targeted lipophilic cationic groups","authors":"","doi":"10.1016/j.tet.2024.134228","DOIUrl":"10.1016/j.tet.2024.134228","url":null,"abstract":"<div><div>Mitochondria have been recognized as a significant target for cancer therapy due to their vital role in many basic cell functions. In recent years, the development of mitochondrial targeted anti-tumor drugs has become important research directions. Herein, We report three new targeted preparations (FEQ-TPP, FEQ-BDP, and FEQ-TEA), which were synthesized by conjugating triphenylphosphine (TPP), Bodipy-pyridine salt (BDP) and triethylamine salt (TEA) with phenoxazine (FEQ). It was observed that greater delocalization range of TPP cationic carriers can enhance the recognition and accumulation efficiency of FEQ-TPP in tumor cell mitochondria. As a result, FEQ-TPP exhibits excellent mitochondrial targeting and significant anti-tumor selectivity; FEQ-BDP can show the ability of real-time fluorescence imaging. This research provides valuable insights for the screening of mitochondrial targeting vectors and the subsequent exploration and development of targeted anti-tumor medications, particularly those based on phenoxazine and its derivatives.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142315252","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
A coumarin-hemicyanine fluorescent probe for simultaneous detection and discrimination of biothiols, HSO3− and S2- 用于同时检测和鉴别生物硫醇、HSO3- 和 S2- 的香豆素-水杨碱荧光探针
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-04 DOI: 10.1016/j.tet.2024.134249
{"title":"A coumarin-hemicyanine fluorescent probe for simultaneous detection and discrimination of biothiols, HSO3− and S2-","authors":"","doi":"10.1016/j.tet.2024.134249","DOIUrl":"10.1016/j.tet.2024.134249","url":null,"abstract":"<div><p>Biomercaptan, bisulfite (HSO<sub>3</sub><sup>−</sup>) and hydrogen sulfide (H<sub>2</sub>S) are involved in many physiological and pathological processes in the human body. Therefore, it is of great significance to develop a fluorescent probe that can simultaneously detect and distinguish biological mercaptans from HSO<sub>3</sub><sup>−</sup> and S<sup>2−</sup>. The probe CDI-1 was synthesized by combining coumarin with hemicyanine. The maximum absorption wavelength of the probe is at 609 nm. After adding Cys/Hcy and GSH, the probe shows varying degrees of blue shift, which can be used to distinguish Cys/Hcy and GSH. After it reacts with Cys/Hcy, the fluorescence intensity of the solution increases about twice, while it increases three times after it reacts with GSH. This phenomenon can also be used to distinguish Cys/Hcy from GSH. The probe CDI-1 can react with Cys completely within 30 min, with Hcy or GSH completely within 80 min, and with HSO<sub>3</sub><sup>−</sup> and S<sup>2−</sup> quickly within 20 min. The study on the effect of pH on the fluorescence performance of CDI-1 shows that the probe is suitable for detecting biological mercaptan or HSO<sub>3</sub><sup>−</sup>, S<sup>2−</sup> in weak acid to weak alkali environments. The selectivity study showed that the probe CDI-1 had high specificity for biological mercaptan, HSO<sub>3</sub><sup>−</sup> and S<sup>2−</sup>. This provides a new and simple method for simultaneous detection of biological mercaptan, HSO<sub>3</sub><sup>−</sup> and S<sup>2−</sup> ions.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142150670","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 of β-lactams and transformation to β-amino acid ethyl ester derivatives: Theoretical calculations β-内酰胺的合成及向β-氨基酸乙酯衍生物的转化：理论计算
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-03 DOI: 10.1016/j.tet.2024.134247
{"title":"Synthesis of β-lactams and transformation to β-amino acid ethyl ester derivatives: Theoretical calculations","authors":"","doi":"10.1016/j.tet.2024.134247","DOIUrl":"10.1016/j.tet.2024.134247","url":null,"abstract":"<div><p>Because of the important biological properties of β-amino acids in the present work, two new β-amino acid ethyl ester derivatives were synthesized, and their mechanistic occurrence was investigated. The title compounds were synthesized from related tetralone derivatives containing bromine and methoxy groups. Tetralone derivatives were reduced to their benzyl alcohol derivatives with NaBH<sub>4,</sub> followed by elimination with <em>p</em>-toluenesulfonic acid (<em>p</em>TSA) to give the desired 1,2-dihydronaphthalene derivatives. The reactions of 1,2-dihydronaphthalenes with chlorosulfonyl isocyanate (CSI) afforded β-lactams. β-Amino acids were obtained from the reaction of β-lactams with EtOH in HCl. Computational studies are concerned with synthesizing four-membered lactams (β-lactam) formed by the reaction between 1,2-dihydronaphthalene derivatives and CSI. The mechanism of the formation of compounds has been elucidated using DFT at M06-2X.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142150671","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
A concise, stereoselective and scalable synthesis of optically pure (3R,4R)-1-benzyl- and (3R,4R)-1-Boc-3-methyl-4-aminopiperidines 光学纯(3R,4R)-1-苄基和(3R,4R)-1-叔丁氧羰基-3-甲基-4-氨基哌啶的简便、立体选择性和可扩展合成方法
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-02 DOI: 10.1016/j.tet.2024.134239
{"title":"A concise, stereoselective and scalable synthesis of optically pure (3R,4R)-1-benzyl- and (3R,4R)-1-Boc-3-methyl-4-aminopiperidines","authors":"","doi":"10.1016/j.tet.2024.134239","DOIUrl":"10.1016/j.tet.2024.134239","url":null,"abstract":"<div><p>An efficient, scalable and stereoselective synthesis of optically pure (<em>3R,4R</em>)-1-benzyl- and (<em>3R,4R</em>)-1-Boc-3-methyl-4-aminopiperidines has been developed starting from commercially available <em>N</em>-benzyl-3-methyl-4-piperidone. The synthesis employed chiral resolution of <em>N</em>-benzyl-3-methyl-4-piperidone, <em>cis</em>-selective reduction of a keto group, and subsequent Mitsunobu inversion of the resulting hydroxy group to install an amine with the desired <em>trans</em>-stereochemistry as the key steps. The method described herein demonstrated a competent route to the title compounds in a cost-effective, and scalable manner.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142135835","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, enantiomeric composition, separation of (L)-menthyl 3-arylglycidates and their reactions with benzene-1,2-diamine (L)-3-芳基缩水甘油酸孟酯的合成、对映体组成、分离及其与苯-1,2-二胺的反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-02 DOI: 10.1016/j.tet.2024.134244
{"title":"Synthesis, enantiomeric composition, separation of (L)-menthyl 3-arylglycidates and their reactions with benzene-1,2-diamine","authors":"","doi":"10.1016/j.tet.2024.134244","DOIUrl":"10.1016/j.tet.2024.134244","url":null,"abstract":"<div><div>The reactions of (L)-menthyl chloroacetate ((1<em>R</em>,2<em>S</em>,5<em>R</em>)-2-isopropyl-5-methylcyclohexyl chloroacetate) with aromatic aldehydes under Darzens condensation conditions produce mixtures of four isomers of (L)-menthyl-3-arylglycidates in approximately equal quantities, of which (L)-menthyl (2<em>S</em>,3<em>S</em>)-3-arylglycidates spontaneously crystallize when kept at the room temperature for a week. (L)-Menthyl (2<em>S</em>,3<em>S</em>)-3-arylglycidates, in contrast to the mixtures of (2<em>S</em>,3<em>R</em>) and (2<em>R</em>,3<em>S</em>) isomers of (L)-menthyl 3-arylglycidates, which in reactions with benzene-1,2-diamine at boiling AcOH give 3-hydroxy-4-aryl-4,5-dihydro-1<em>H</em>-benzo[<em>b</em>][1,4]diazepin-2(3<em>H</em>)-ones, provide enantioselective formation of (L)-menthyl (2<em>S</em>,3<em>S</em>)-2-hydroxy-3-(2-methylbenzimidazol-1-yl)-3-arylpropanoates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425564","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
Photoredox-catalyzed self-dimerization and cross-addition as well as Zn(OTf)2-mediated nucleophile coupling: A novel route to structurally diverse 2,2-disubstituted indolin-3-ones 光氧化催化的自二聚化和交叉加成以及 Zn(OTf)2 介导的亲核偶联：获得结构多样的 2,2-二取代吲哚啉-3-酮的新途径
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-02 DOI: 10.1016/j.tet.2024.134242
{"title":"Photoredox-catalyzed self-dimerization and cross-addition as well as Zn(OTf)2-mediated nucleophile coupling: A novel route to structurally diverse 2,2-disubstituted indolin-3-ones","authors":"","doi":"10.1016/j.tet.2024.134242","DOIUrl":"10.1016/j.tet.2024.134242","url":null,"abstract":"<div><p>An efficient protocol for the synthesis of 2,2-disubstituted indolin-3-ones from both 2-aryl and 2-alkyl indoles via photoredox-catalyzed self-dimerization and cross-addition as well as Zn(OTf)<sub>2</sub>-mediated nucleophile coupling is described. The photoredox reactions feature low catalyst loading, mild reaction conditions, and broad functional group tolerance, generating indolin-3-ones in moderate to excellent yields. The Zn(OTf)<sub>2</sub>-mediated transformation using indolin-3-one dimer as a newly active species provides a much gentle way to access structurally diverse indolin-3-ones.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142150749","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
An alternative and scalable synthesis for Relugolix 一种可替代和可扩展的瑞乐高合成方法
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-02 DOI: 10.1016/j.tet.2024.134243
{"title":"An alternative and scalable synthesis for Relugolix","authors":"","doi":"10.1016/j.tet.2024.134243","DOIUrl":"10.1016/j.tet.2024.134243","url":null,"abstract":"<div><p>An alternative and efficient synthetic route for Relugolix was accomplished by changing the construction order of three main parts A, B and C. After the optimization, its scale-up of the preparation for Relogulix was completed in a seven-step methodology with overall yield of 61 % and 99.62 % HPLC purity.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142136324","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
Decarboxylation and cross-coupling reactions of coumarin-3-carboxylic acid: A comprehensive review 香豆素-3-羧酸的脱羧和交叉偶联反应：全面综述
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-01 DOI: 10.1016/j.tet.2024.134238
{"title":"Decarboxylation and cross-coupling reactions of coumarin-3-carboxylic acid: A comprehensive review","authors":"","doi":"10.1016/j.tet.2024.134238","DOIUrl":"10.1016/j.tet.2024.134238","url":null,"abstract":"<div><p>The present review article offers an overview of the application of coumarin-3-carboxylic acids as a promising synthon in the synthesizing a diverse array of interesting biologically relevant organic molecules. This is accomplished, primarily through cross-coupling reactions, followed by subsequent decarboxylation, resulting in new reactivity patterns. The ability of the carboxylic acid moiety to enhance the electrophilic character of the directly attached olefinic carbon within a coumarin moiety, along with its feasibility for decarboxylation, opens up straightforward synthetic routes for numerous coumarin-derived molecules, including fused and hybrid heterocycles with remarkable regioselectivity (3-addition, 4-addition, or both). These advancements are primarily based on cascade reactions. This review article aims to provide readers with an up-to-date overview, encompassing contributions predominantly made in this challenging domain of organic synthesis during the last decade.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142135834","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
On the flexibility of 1,4-bis(phenylethynyl)benzene butyl ester organic crystal featuring mobile components 论具有流动成分的 1,4-双（苯乙炔基）苯丁酯有机晶体的柔韧性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-09-01 DOI: 10.1016/j.tet.2024.134245
{"title":"On the flexibility of 1,4-bis(phenylethynyl)benzene butyl ester organic crystal featuring mobile components","authors":"","doi":"10.1016/j.tet.2024.134245","DOIUrl":"10.1016/j.tet.2024.134245","url":null,"abstract":"<div><p>The quest for organic materials with compliant mechanical properties has significantly increased in the past few years in materials science and engineering. Crystalline organic compounds are excellent candidates for exploring and developing those long-lasting properties in the solid state since their fine structural functionalization may provide them with unique flexible behaviors. This study describes the 1,4-bis(phenylethynyl)benzene butyl ester synthesized in four steps and whose crystal can display elastic and elasto-plastic responses upon action with an external stimulus. A detailed characterization by single crystal X-ray diffraction revealed a layered crystal array that results from π-π stacking interactions, C–H⋯O and C-H⋯π bonds. Complementarily, variable temperature solid-state <sup>13</sup>C and <sup>2</sup>H NMR studies were carried out to probe the motion of the different components of the molecule and explore their possible association with the mechanical features. The compiled evidence indicates that the central phenylenes and the butyl groups experience molecular motion at different timescales, which, combined with the crystal array, facilitate the observed elastic and elasto-plastic flexibility. The results presented here not only contribute to advancing our understanding of flexible behavior but also could inspire potential applications such as flexible electronics.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0040402024004253/pdfft?md5=cf7011610b11332868a4c586ec54550b&pid=1-s2.0-S0040402024004253-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142150669","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}
引用次数: 0
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