Tetrahedron chem最新文献_第7页

Triquinane based natural products via cycloadditions and metathesis 通过环加成和偏合成获得基于三喹烷的天然产品

Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-10-25 DOI: 10.1016/j.tchem.2024.100103

Subba Rao Cheekatla

{"title":"Triquinane based natural products via cycloadditions and metathesis","authors":"Subba Rao Cheekatla","doi":"10.1016/j.tchem.2024.100103","DOIUrl":"10.1016/j.tchem.2024.100103","url":null,"abstract":"<div><div>Triquinane natural products are an interesting class of polycyclic frameworks that have attracted considerable interest because of their distinct structures and diverse array of biological applications such as antibacterial, antifungal, and anticancer properties and biological diversity of these scaffolds make them promising candidates for drug discovery and medicinal chemistry. These frameworks have a central structure of bicyclo[2.2.1]heptane ring which is linked to another cycloalkane ring generating the a unique tricyclic arrangement. The design and synthesis of triquinane framework is very challenging because of their intricate three-dimensional structure and the requirement for accurate organization of numerous stereocenters. Based on thorough review of literature, cycloadditions and metathesis play a pivotal role for constructing these exciting class of complex frameworks in an efficient and selective manner. In this review we focused mainly on how cycloadditions and metathesis strategies are significant in total synthesis of these interesting class of scaffolds. Here, we summarized the synthetic strategies of linear, angular, and propellane types of triquinane natural products <em>via</em> different cycloaddition protocols as well as photothermal and olefin metathesis which are used as key steps in the total synthesis.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100103"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142551884","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Highly efficient and selective anticancer approach through acrolein-triggered cycloaddition chemistry in patient-derived xenografts: Mechanistic and preclinical investigation 通过丙烯醛引发的环加成化学在患者来源的异种移植物中高效和选择性的抗癌方法：机制和临床前研究

Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-09-17 DOI: 10.1016/j.tchem.2024.100094

Yuria Takahashi , Kazuki Terashima , Taiji Shimoda , Masayuki Nagahashi , Koji Morimoto , Sayaka Urano , Kozo Kataoka , Hisashi Shinohara , Yasuo Miyoshi , Ambara R. Pradipta , Katsunori Tanaka

{"title":"Highly efficient and selective anticancer approach through acrolein-triggered cycloaddition chemistry in patient-derived xenografts: Mechanistic and preclinical investigation","authors":"Yuria Takahashi , Kazuki Terashima , Taiji Shimoda , Masayuki Nagahashi , Koji Morimoto , Sayaka Urano , Kozo Kataoka , Hisashi Shinohara , Yasuo Miyoshi , Ambara R. Pradipta , Katsunori Tanaka","doi":"10.1016/j.tchem.2024.100094","DOIUrl":"10.1016/j.tchem.2024.100094","url":null,"abstract":"<div><div>The efficacy of anticancer treatments in the clinical setting can be improved by decreasing off-target effects. Chemistry-based methods are emerging as a promising strategy to overcome this limitation. We previously developed a prodrug strategy using mitomycin C (MMC) activated at the tumor site by the [3 + 2] cycloaddition of endogenous acrolein, which is overexpressed in various cancers. Herein, we report the results of mechanistic and preclinical studies using a prodrug of doxorubicin (DOX), which is used in the treatment of several cancers, but its dosage is restricted by off-target effects. First, we developed robust chemistry methods for the synthesis of large amounts of prodrug for animal experiments. The DOX prodrug showed high anticancer efficacy without off-target effects even at high doses. Pharmacokinetic/pharmacodynamic, biodistribution, and serum protein binding studies supported the <em>in vivo</em> anticancer efficacy of DOX derivatization with the hydrophobic 2,6-diisopropyl azidobenzylcarbamate protecting group. This enhanced albumin binding, thereby increasing circulatory residence (serum stability). The stabilized prodrug could only be activated at the tumor site by reacting with endogenous acrolein to gradually release the required amounts of drug. Inhibiting overproduction of the drug and its circulation back into the blood minimized off-target effects. Nonspecific organ accumulation was not observed, supporting the safety of the prodrug <em>in vivo</em>. DOX and MMC prodrugs showed selective anticancer efficacy against patient-derived samples from lung, colorectal, gastric, and breast cancers. The proposed <em>in vivo</em> chemical strategy should be tested in clinical trials in the future.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100094"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129869","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Automation in electrifying flow organic synthesis 电气化流动有机合成的自动化

Tetrahedron chem Pub Date : 2024-12-01 Epub Date: 2024-10-24 DOI: 10.1016/j.tchem.2024.100105

Tomas Hardwick, Nisar Ahmed

引用次数: 0

l-Proline catalyzed synthesis of biologically promising heterocycles under sustainable conditions 可持续条件下 l-脯氨酸催化合成具有生物前景的杂环化合物

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-08-06 DOI: 10.1016/j.tchem.2024.100087

Rajiv Karmakar , Chhanda Mukhopadhyay

{"title":"l-Proline catalyzed synthesis of biologically promising heterocycles under sustainable conditions","authors":"Rajiv Karmakar , Chhanda Mukhopadhyay","doi":"10.1016/j.tchem.2024.100087","DOIUrl":"10.1016/j.tchem.2024.100087","url":null,"abstract":"<div><p>Catalysis field wherein a tiny organic molecule like <span><em>l</em></span>-proline is an efficient and selectively catalyzed organic reaction. Catalyst-supported organic synthesis is confirmed to be involved in the fast synthesis of novel compounds with selectivity and enhanced biological activities. <span><em>l</em></span>-proline catalyzed reactions are valuable tools for the making of different heterocycles, acyclic, and carbocyclic scaffolds that signify the main framework of most of the bio-active compounds. A few decades ago, novel tools for the manufacturing of bio-active molecules had a huge impact on organic chemistry. Subsequently, the synthesis of biologically important heterocycles through a synthetically proficient and environmentally benign route is the important purpose of modern synthetic chemistry. In this review, we discuss only <span><em>l</em></span>-proline catalyzed organic reactions (including condensation, addition, asymmetric, multi-components, and other modular reactions) for the sustainable synthesis of biologically promising heterocycles in a single trencher that may provide as a piece of reliable literature for further research in this field.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100087"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000263/pdfft?md5=7360970aaabda90d1ad3e7b8516a7217&pid=1-s2.0-S2666951X24000263-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141943434","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study 8 元氮杂环丁烷的快速合成：综合合成、DFT 和体外研究

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-07-17 DOI: 10.1016/j.tchem.2024.100085

Heorhii V. Posternak , Olena D. Semoshkina , Vasyl Y. Hys , Demyd S. Milokhov , Pavlo A. Virych , Svitlana V. Shishkina , Yulian M. Volovenko , Alexey V. Dobrydnev

{"title":"Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study","authors":"Heorhii V. Posternak , Olena D. Semoshkina , Vasyl Y. Hys , Demyd S. Milokhov , Pavlo A. Virych , Svitlana V. Shishkina , Yulian M. Volovenko , Alexey V. Dobrydnev","doi":"10.1016/j.tchem.2024.100085","DOIUrl":"10.1016/j.tchem.2024.100085","url":null,"abstract":"<div><p>Herein we describe the novel approach to the synthesis of functionalized ind(az)olo-fused 1,2,4-thiadiazocine 1,1-dioxides through the CSIC (<em>Carbanion-mediated Sulfonate (Sulfonamide) Intermolecular Coupling (Intramolecular Cyclization</em>) reaction strategy. 1,2,4-Thiadiazocine 1,1-dioxides (put simply 8-membered <em>aza</em>sultams) are increasingly popular but quite underrepresented in the literature compounds, were prepared in two simple steps and good yield from readily available reagents. Particularly, the alkylation of 7-functionalized ind(az)oles with <em>N</em>-(chloromethyl)-<em>N</em>-methylmethanesulfonamide gave the corresponding <em>N</em>-((1<em>H</em>-ind(az)ol-1-yl)methyl)-<em>N</em>-methylmethane-sulfonamides which underwent base-mediated cyclization affording the target 8-membered <em>aza</em>sultams. The method worked well and provided <em>aza</em>sultams decorated with a set of synthetically valuable handles. The conducted DFT calculations explained and rationalized the experimental data thus allowing us to formulate the rules of the structure‒activity relationship. Despite the prepared compounds showing weak cytotoxicity against the MDA-MB-231 breast cancer cell line, they are considered novel building blocks and perspective pharmacological templates prone to further optimization.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100085"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X2400024X/pdfft?md5=8a5acacf07f97bf098fa955907034fa1&pid=1-s2.0-S2666951X2400024X-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141728620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Fluoroalcohols for chemical modification of biomolecules 用于生物大分子化学修饰的氟醇

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-08-06 DOI: 10.1016/j.tchem.2024.100088

Mohammad Nuruzzaman , Zeinab M. Nizam , Jun Ohata

引用次数: 0

Repurposing HER catalysis toward metal hydride-mediated electro-reductive transformations 将 HER 催化重新用于金属氢化物介导的电还原转化

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-06-27 DOI: 10.1016/j.tchem.2024.100080

Sheng Zhang, Man-Bo Li

{"title":"Repurposing HER catalysis toward metal hydride-mediated electro-reductive transformations","authors":"Sheng Zhang, Man-Bo Li","doi":"10.1016/j.tchem.2024.100080","DOIUrl":"https://doi.org/10.1016/j.tchem.2024.100080","url":null,"abstract":"<div><p>Hydrogen evolution reaction (HER) is known as one of the most cardinal reactions in energy chemistry. In the field, tremendous efforts have been devoted to discovering highly efficient catalysts and investigating the reaction mechanism. Metal hydrides are the most critical intermediates in the HER catalysis, and they also exhibit versatile reactivity in organic transformations. Redirecting HER catalysis for metal hydride-mediated electrochemical transformations would provide effective solutions for some challenging issues in conventional organic chemistry. Although some remarkable progress has recently been achieved in the cross-subject, the synthetic chemistry community has yet to fully understand the related catalytic mechanism and catalyst design. Herein, we conclude the catalytic HER mechanism and catalyst design principles to facilitate the repurposing HER catalysis toward organic electrochemistry. Recent examples of metal hydride-mediated electro-reductive transformations have also been covered, including the reduction of unsaturated bonds and the functionalization of C–H bonds. Additionally, we discussed challenges and future developments in the field.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100080"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000196/pdfft?md5=69ceaa5807bacf0325ed1656a32e9535&pid=1-s2.0-S2666951X24000196-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141486682","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Atroposelective total synthesis of strecintide 839 斯特林肽的逆选择全合成 839

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-07-10 DOI: 10.1016/j.tchem.2024.100084

Hiroshige Ogawa, Hugh Nakamura

引用次数: 0

Biocatalytic reactions, crystal structures and mechanisms of kynurenine formamidases 犬尿氨酸甲酰胺酶的生物催化反应、晶体结构和机制

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-06-10 DOI: 10.1016/j.tchem.2024.100077

Changmei Liu , Chengyue Miao , Xiaorui Chen , Yan Zhang , Yijian Rao , Zhenbo Yuan

{"title":"Biocatalytic reactions, crystal structures and mechanisms of kynurenine formamidases","authors":"Changmei Liu , Chengyue Miao , Xiaorui Chen , Yan Zhang , Yijian Rao , Zhenbo Yuan","doi":"10.1016/j.tchem.2024.100077","DOIUrl":"https://doi.org/10.1016/j.tchem.2024.100077","url":null,"abstract":"<div><p>Kynurenine (Kyn) as a non-proteinogenic amino acid, is prevalent in various bioactive natural products, and plays a pivotal role in metabolism and related diseases. Thus, several synthetic methods toward Kyn have been established with the employment of acid/base-mediated hydrolysis reaction to remove the formyl group of <em>N</em>-formylkynurenine (NFK), which is not satisfied with the trend of green chemistry. Learning from nature, kynurenine formamidase is considered a promising biocatalyst to realize the hydrolysis of NFK as alternative to the environmentally unfriendly acid or base. For these reasons, interest in the kynurenine formamidase has increased, but the research area still remains relatively underexplored. In this review, the recent investigations on the biocatalytic reactions, crystal structures and mechanisms of the kynurenine formamidases in combination with the homologous enzymes with inferred kynurenine formamidase activity are summarized. This review may help researchers understand kynurenine formamidase further and apply them in the preparation of Kyn for natural products synthesis and drug development.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100077"},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000160/pdfft?md5=9ac8cf7e28a6ada9565c2b45b1d4231c&pid=1-s2.0-S2666951X24000160-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141333242","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Electrochemical oxidations through hypervalent iodine redox catalysis 通过超价碘氧化还原催化实现电化学氧化

Tetrahedron chem Pub Date : 2024-08-01 Epub Date: 2024-07-05 DOI: 10.1016/j.tchem.2024.100081

Ronit S. Bernard , Ajit Kumar Jha , Marcin Kalek

引用次数: 0