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Design of a chiral molecular pocket in a Ni(II) complex to improve stereoselectivity in the kinetic resolution of racemic epoxides with CO2 Ni（II）配合物中手性分子袋的设计以提高外消旋环氧化合物与CO2的动力学拆分的立体选择性
Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100115
Mikhail A. Emelyanov , Alexander V. Bachinskiy , Yana V. Derkach , Vasiliy A. Chaliy , Alexander F. Smol'yakov , Michael G. Medvedev , Aleksei A. Titov , Victor I. Maleev , Vladimir A. Larionov
{"title":"Design of a chiral molecular pocket in a Ni(II) complex to improve stereoselectivity in the kinetic resolution of racemic epoxides with CO2","authors":"Mikhail A. Emelyanov ,&nbsp;Alexander V. Bachinskiy ,&nbsp;Yana V. Derkach ,&nbsp;Vasiliy A. Chaliy ,&nbsp;Alexander F. Smol'yakov ,&nbsp;Michael G. Medvedev ,&nbsp;Aleksei A. Titov ,&nbsp;Victor I. Maleev ,&nbsp;Vladimir A. Larionov","doi":"10.1016/j.tchem.2024.100115","DOIUrl":"10.1016/j.tchem.2024.100115","url":null,"abstract":"<div><div>The kinetic resolution of racemic epoxides using the carbon dioxide (CO<sub>2</sub>) molecule is of significant practical interest because the reaction yields the valuable products – enantiomerically enriched cyclic carbonates (1,3-dioxolan-2-ones), along with the remaining opposite enantiomer of the epoxide. However, one is the main challenges in this direction is the absence of the universal and efficient chiral catalytic systems for the resolution of different epoxides by CO<sub>2</sub> with a high selectivity factor (<em>s</em>). In this context, we herein present a perspective proof-of-concept approach for the improvement of stereoselectivity in the resolution of terminal epoxides by a rational design of an appropriate chiral molecular pocket in a Ni(II) complex based on commercially available (<em>S</em>)-(2-aminomethyl)pyrrolidine and 3,5-di-<em>tert</em>-butylsalicylaldehyde. The obtained chiral Ni(II) complex with iodide-anion catalyzes the kinetic resolution of epoxides by CO<sub>2</sub> with <em>s</em>-factor up to 7.8, while the addition of a suitable chiral ligand to this system, particularly, (<em>S</em>)-(2-anilinomethyl)pyrrolidine led to the increasing of <em>s</em>-factor up to 11.5 in the case of challenging styrene oxide (<em>ee</em> of styrene cyclic carbonate was 82%) which is being one of the best results for this substrate to date. It is gratifying to note that even achiral co-ligands can be used, greatly simplifying the catalytic system. The experimental and spectral data and DFT calculations revealed the mechanism of catalysis and enantioselection.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100115"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142757076","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
Photo- and electro-chemical strategies for indazole synthesis 吲哚唑合成的光电化学策略
Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100116
Binbin Huang
{"title":"Photo- and electro-chemical strategies for indazole synthesis","authors":"Binbin Huang","doi":"10.1016/j.tchem.2024.100116","DOIUrl":"10.1016/j.tchem.2024.100116","url":null,"abstract":"<div><div>The indazole core is prevalently found in the structures of bioactive molecules, demonstrating promising potential in medicinal chemistry and drug discovery, which therefore has attracted sustained attention from the synthetic community. Over the recent decades, significant progress has been achieved in both organic photocatalysis and electrosynthesis, offering novel approaches for the efficient and sustainable synthesis of various functionalized indazoles. This mini-review highlights the emerging methodological advancements in photo-/electro-chemical synthesis of two common forms of indazole, namely 1<em>H</em>- and 2<em>H</em>-indazoles, which are classified by specific intramolecular bond formation patterns: (1) C–C bond formation, (2) C–N bond formation, and (3) N–N bond formation. The reaction conditions, representative scopes, and mechanistic understandings of these protocols are emphasized, to elucidate the advantages and limitations in current strategies, with an aim to inspire future innovations that may address challenges in modern indazole synthesis.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100116"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129867","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
Synthesis of allenones via nickel-catalyzed reductive coupling of propargyl esters with acyl chlorides 丙炔酯与酰基氯化物镍催化还原偶联合成烯酮
Tetrahedron chem Pub Date : 2024-12-01 DOI: 10.1016/j.tchem.2024.100113
Zhen Song, Yueming Wang, Ming Ma, Yuanhong Ma
{"title":"Synthesis of allenones via nickel-catalyzed reductive coupling of propargyl esters with acyl chlorides","authors":"Zhen Song,&nbsp;Yueming Wang,&nbsp;Ming Ma,&nbsp;Yuanhong Ma","doi":"10.1016/j.tchem.2024.100113","DOIUrl":"10.1016/j.tchem.2024.100113","url":null,"abstract":"<div><div>Transition metal-catalyzed reductive coupling of two electrophilic components has proved to be a powerful and step-economic tool for forging diverse organic molecules. However, the application of such strategy for the synthesis of allenones that are very important in pharmaceutical chemistry and synthetic chemistry remains very limited and challenging. Herein, we have developed a nickel-catalyzed reductive cross-coupling of propargyl esters with acyl chlorides, which affords an alternative route for the synthesis of allenones. The current catalytic protocol features readily available starting materials, wide substrate scope, mild conditions and good regioselectivity.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100113"},"PeriodicalIF":0.0,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143129868","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 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 ,&nbsp;Kazuki Terashima ,&nbsp;Taiji Shimoda ,&nbsp;Masayuki Nagahashi ,&nbsp;Koji Morimoto ,&nbsp;Sayaka Urano ,&nbsp;Kozo Kataoka ,&nbsp;Hisashi Shinohara ,&nbsp;Yasuo Miyoshi ,&nbsp;Ambara R. Pradipta ,&nbsp;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
Recent trends in the identification and engineering of halogenases 卤素酶鉴定和工程设计的最新趋势
Tetrahedron chem Pub Date : 2024-11-19 DOI: 10.1016/j.tchem.2024.100112
Huibin Wang , Ikuro Abe
{"title":"Recent trends in the identification and engineering of halogenases","authors":"Huibin Wang ,&nbsp;Ikuro Abe","doi":"10.1016/j.tchem.2024.100112","DOIUrl":"10.1016/j.tchem.2024.100112","url":null,"abstract":"<div><div>Halogenation significantly enhances the biological activity, stability, and solubility of organic molecules, and thus is a crucial modification in the biotechnology and pharmaceutical industries. Halogenases, the core enzymes responsible for this transformation, are invaluable tools for the selective incorporation of halogens into diverse substrates, offering vast potential in drug development and synthetic biology. Recent discoveries of novel classes of halogenases have substantially expanded the repertoire of enzymatic halogenation. In parallel, remarkable progress in the protein engineering of halogenases is leading to unprecedented opportunities in the synthesis of novel compounds. These efforts have not only expanded the substrate scope, improved the selectivity, and enhanced the catalytic activity but also demonstrated their capacity for new-to-nature reactions. This perspective article highlights critical developments in the identification and engineering of halogenases, underscoring their growing significance in biocatalysis and sustainable chemical production. Continued exploration of novel halogenases, coupled with advanced protein engineering strategies, will open new frontiers in biocatalyst development and drug discovery.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100112"},"PeriodicalIF":0.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705642","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
Tyrosine bioconjugation using stably preparable urazole radicals 利用可稳定制备的脲唑自由基进行酪氨酸生物键合
Tetrahedron chem Pub Date : 2024-11-19 DOI: 10.1016/j.tchem.2024.100111
Shinichi Sato , Shogo Miyano , Keita Nakane , Zhengyi Liu , Munehiro Kumashiro , Tomohide Saio , Yuya Tanaka , Akira Shigenaga , Chizu Fujimura , Eri Koyanagi , Hafumi Nishi , Shusuke Tomoshige , Minoru Ishikawa
{"title":"Tyrosine bioconjugation using stably preparable urazole radicals","authors":"Shinichi Sato ,&nbsp;Shogo Miyano ,&nbsp;Keita Nakane ,&nbsp;Zhengyi Liu ,&nbsp;Munehiro Kumashiro ,&nbsp;Tomohide Saio ,&nbsp;Yuya Tanaka ,&nbsp;Akira Shigenaga ,&nbsp;Chizu Fujimura ,&nbsp;Eri Koyanagi ,&nbsp;Hafumi Nishi ,&nbsp;Shusuke Tomoshige ,&nbsp;Minoru Ishikawa","doi":"10.1016/j.tchem.2024.100111","DOIUrl":"10.1016/j.tchem.2024.100111","url":null,"abstract":"<div><div>Our <em>ex situ</em> tyrosine bioconjugation method utilizes the oxidation of <em>N</em>-methylurazole by Bobbitt's salt or electrochemical activation to generate stable radicals for selective tyrosine labeling, thereby addressing the longstanding challenges in protein bioconjugation. Unlike traditional tyrosine conjugation techniques that rely on closed-shell chemistry with 1,2,4-triazoline-3,5-dione derivatives, this method introduces an alternative bond-forming mechanism that expands bioconjugation through a radical-based pathway that enhances tyrosine selectivity. The applicability of this method was demonstrated for various proteins and validated through proteome-wide analyses, highlighting its potential as a valuable tool for investigating protein function and interaction dynamics.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100111"},"PeriodicalIF":0.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705643","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
A modern approach to intermittent illumination for the characterization of chain-propagation in photoredox catalysis 间歇照明用于表征光氧化催化过程中链式传播的现代方法
Tetrahedron chem Pub Date : 2024-11-12 DOI: 10.1016/j.tchem.2024.100110
K.A. Viraj Miyuranga , Kaitlin E. Ashcraft , Spencer P. Pitre
{"title":"A modern approach to intermittent illumination for the characterization of chain-propagation in photoredox catalysis","authors":"K.A. Viraj Miyuranga ,&nbsp;Kaitlin E. Ashcraft ,&nbsp;Spencer P. Pitre","doi":"10.1016/j.tchem.2024.100110","DOIUrl":"10.1016/j.tchem.2024.100110","url":null,"abstract":"<div><div>Photoredox catalysis has become an invaluable tool for the construction of organic molecules, allowing for unparalleled control over radical intermediates enabled by the mild conditions achieved through visible-light activation of a photocatalyst. These reactions can be classified under two distinct mechanistic paradigms: closed photocatalytic cycles, and photoinitiated chain reactions. While optimization strategies for each of these classes of reaction differ significantly, organic chemists still lack a straightforward means for probing chain-propagation. In this work, we report a simple and accessible approach to performing intermittent illumination studies for characterizing chain reactions in photoredox catalysis. Using modern LED technologies to precisely control the rate of sample illumination, we were able to validate the presence or absence of product-forming chain reactions in four previously reported photoredox protocols. Furthermore, this technique also allows for the determination of chain-propagating lifetimes through a simple graphical analysis. Given the operational simplicity and ease of accessibility, we believe this intermittent illumination technique will be of great value to practitioners of the field moving forward.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100110"},"PeriodicalIF":0.0,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142653834","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
Recent advances in catalytic carbofluorination of unsaturated system via C–F bond reconstruction 通过 C-F 键重构催化不饱和体系羧基氟化的最新进展
Tetrahedron chem Pub Date : 2024-11-06 DOI: 10.1016/j.tchem.2024.100109
Yaxin Zeng, Xufei Yan, Ying Xia
{"title":"Recent advances in catalytic carbofluorination of unsaturated system via C–F bond reconstruction","authors":"Yaxin Zeng,&nbsp;Xufei Yan,&nbsp;Ying Xia","doi":"10.1016/j.tchem.2024.100109","DOIUrl":"10.1016/j.tchem.2024.100109","url":null,"abstract":"<div><div>The distinctive properties of the fluorine atom confer significant advantages to organofluorine compounds in pharmaceuticals, agrochemicals, and materials science. A particularly promising approach for synthesizing these compounds involves atom-economical carbofluorination reactions. These reactions involve the activation of a carbon-fluorine (C–F) bond, then facilitating the incorporation of both a carbon-based fragment and a fluorine atom into an unsaturated system. The capacity to reintegrate the fluorine atom from the starting material into the final product, known as fluoride recycling via C–F bond reconstruction, is advantageous in terms of both atom and step economy. This review highlights recent advancements in catalytic C–F bond reconstruction, encompassing the background, chemical transformations, reaction scope, synthetic applications, mechanisms, and future research directions.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100109"},"PeriodicalIF":0.0,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142653833","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
Efficient construction of a quinoline framework from alcohols, nitroarenes, and alkenes promoted by a trimetallic catalyst system 在三金属催化剂体系的促进下，从醇、硝基烯烃和烯烃中高效构建喹啉框架
Tetrahedron chem Pub Date : 2024-11-02 DOI: 10.1016/j.tchem.2024.100108
Rikiya Horikawa , Gen Onodera , Tsutomu Fukuda , Masanari Kimura
{"title":"Efficient construction of a quinoline framework from alcohols, nitroarenes, and alkenes promoted by a trimetallic catalyst system","authors":"Rikiya Horikawa ,&nbsp;Gen Onodera ,&nbsp;Tsutomu Fukuda ,&nbsp;Masanari Kimura","doi":"10.1016/j.tchem.2024.100108","DOIUrl":"10.1016/j.tchem.2024.100108","url":null,"abstract":"<div><div>A Pd/Fe/In-trimetallic catalyst system promotes the three-component coupling reaction of primary alcohols, nitroarenes, and terminal alkenes to construct quinoline frameworks in a single operation. These consecutive coupling reactions proceed via an oxidative Povarov reaction of alkenes and aldimines derived from primary alcohols and nitroarenes by a redox hydrogen transfer system. This reaction may contribute to the efficient development of pharmaceuticals and medicinal products.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100108"},"PeriodicalIF":0.0,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592932","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
Palladium iodide catalyzed oxidative carbonylations 碘化钯催化氧化羰基化反应
Tetrahedron chem Pub Date : 2024-11-01 DOI: 10.1016/j.tchem.2024.100107
Bartolo Gabriele
{"title":"Palladium iodide catalyzed oxidative carbonylations","authors":"Bartolo Gabriele","doi":"10.1016/j.tchem.2024.100107","DOIUrl":"10.1016/j.tchem.2024.100107","url":null,"abstract":"<div><div>Since the first publication in 1992, the PdI<sub>2</sub>/KI-catalyzed oxidative carbonylation reaction has emerged as a powerful methodology for the multicomponent and sustainable synthesis of high value added carbonylated compounds (esters, amides, lactones, lactams, ureas, oxazolidinones, cyclic carbonates, and so on) starting from simple feedstocks (alkynes, alcohols, amines, etc) in combination with carbon monoxide as the simplest and atom-economical source of the carbonyl group. The main feature of this methodology is related to the possibility to catalytically assembly several simple units in an ordered sequence to produce carbonylated derivatives in a selective way under conditions that employ the greenest and most convenient oxidation agent available (that is, oxygen from air) with formation of water as benign coproduct.</div><div>In this Review, I will illustrate the achievements that have been realized in this exciting field of research in the course of the years.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100107"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142721559","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
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