Beilstein Journal of Organic Chemistry最新文献_第10页

Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles 利用乌基反应中的无保护失活胺和芳基乙二醛合成融合复合氮杂环

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-25 DOI: 10.3762/bjoc.20.154

Javier Gómez-Ayuso, Pablo Pertejo, Tomás Hermosilla, Israel Carreira-Barral, Roberto Quesada, María García-Valverde

{"title":"Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles","authors":"Javier Gómez-Ayuso, Pablo Pertejo, Tomás Hermosilla, Israel Carreira-Barral, Roberto Quesada, María García-Valverde","doi":"10.3762/bjoc.20.154","DOIUrl":"https://doi.org/10.3762/bjoc.20.154","url":null,"abstract":"Abstract\u0000Piperazines and diazepines are examples of nitrogen heterocycles present in many marketed drugs highlighting their importance in the discovery of novel bioactive compounds. However, their synthesis often faces challenges, including complex functionalization and lengthy reaction sequences. Multicomponent reactions, notably the Ugi reaction, have emerged as powerful tools to address these hurdles. Here, we have demonstrated the possibility of using the combination of arylglyoxals and carboxylic acids tethered to nonprotected deactivated amines as a powerful strategy for the synthesis of complex fused heterocycles. The limited nucleophilic character of the amino group of the anthranilic acid, indole-2-carboxylic acid, pyrrole-2-carboxylic acid or N-phenylglycine has allowed the use of these compounds in the Ugi reaction without triggering competitive reactions. The additional functional group present in the resulting Ugi adduct can be leveraged in different post-condensation strategies to easily generate multiple fused nitrogen heterocycles including benzodiazepinone and piperazinone cores.\u0000<img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-154-graphical-abstract.png?max-width=550' border='0'/>\u0000Beilstein J. Org. Chem. 2024, 20, 1758–1766. doi:10.3762/bjoc.20.154","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784067","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}

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Synthesis and characterization of 1,2,3,4-naphthalene and anthracene diimides 1,2,3,4-萘和蒽二亚胺的合成与表征

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-25 DOI: 10.3762/bjoc.20.155

Adam D. Bass, Daniela Castellanos, Xavier A. Calicdan, Dennis D. Cao

引用次数: 0

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs) 利用连续流电化学氧化法合成多环芳香族醌类化合物：多环芳香族苯酚（PAPs）的阳极甲氧基化反应

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-24 DOI: 10.3762/bjoc.20.153

Hiwot M. Tiruye, Solon Economopoulos, Kåre B. Jørgensen

{"title":"Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)","authors":"Hiwot M. Tiruye, Solon Economopoulos, Kåre B. Jørgensen","doi":"10.3762/bjoc.20.153","DOIUrl":"https://doi.org/10.3762/bjoc.20.153","url":null,"abstract":"Abstract\u0000The electrochemical oxidation of polycyclic aromatic phenols (PAPs) has been developed in a microfluidic cell to synthesize polycyclic aromatic quinones (PAQs). Methanol was used as nucleophile to trap the phenoxonium cation formed in the oxidation as an acetal, that later were hydrolysed to the quinone. Formation of hydrogen gas as the cathode reaction caused challenges in the flow cell and were overcome by recycling the reaction mixture through the cell at increased flow rate several times. The specific quinones formed were guided by the position of an initial hydroxy group on the polycyclic aromatic hydrocarbon. An available para-position in the PAPs gave p-quinones, while hydroxy groups in the 2- or 3-position led to o-quinones. The substrates were analysed by cyclic voltammetry for estitmation of the HOMO/LUMO energies to shed more light on this transformation. The easy separation of the supporting electrolyte from the product will allow recycling and makes this a green transformation.\u0000<img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-153-graphical-abstract.png?max-width=550' border='0'/>\u0000Beilstein J. Org. Chem. 2024, 20, 1746–1757. doi:10.3762/bjoc.20.153","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"40 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784071","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

Syntheses and medicinal chemistry of spiro heterocyclic steroids 螺环杂环类固醇的合成与药物化学

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-24 DOI: 10.3762/bjoc.20.152

Laura L. Romero-Hernández, Ana Isabel Ahuja-Casarín, Penélope Merino-Montiel, Sara Montiel-Smith, José Luis Vega-Báez, Jesús Sandoval-Ramírez

{"title":"Syntheses and medicinal chemistry of spiro heterocyclic steroids","authors":"Laura L. Romero-Hernández, Ana Isabel Ahuja-Casarín, Penélope Merino-Montiel, Sara Montiel-Smith, José Luis Vega-Báez, Jesús Sandoval-Ramírez","doi":"10.3762/bjoc.20.152","DOIUrl":"https://doi.org/10.3762/bjoc.20.152","url":null,"abstract":"Abstract\u0000There is compelling evidence that incorporating a heterocyclic moiety into a steroid can alter its pharmacological and pharmacokinetic properties, driving intense interest in the synthesis of such hybrids among research groups. In this review, we present an overview of recent synthetic methodologies, spanning the period from 2000 to 2023, for the preparation of spiro heterocyclic steroids. The compounds surveyed encompass four-, five-, six-, and seven-membered heterocycles appended to various positions of steroidal backbones, with spirocycles containing oxygen, nitrogen, and sulfur atoms being predominant. The outlined synthetic procedures emphasize the pivotal steps for constructing the heterocycles, often accompanied by a detailed account of the overall synthesis pathway. The review encompasses innovative compounds, including bis-steroids linked by a spiro heterocycle and steroids conjugated to heterocyclic moieties containing three or more (hetero)cycles. Moreover, many compounds are accompanied by data on their biological activities, such as antiproliferative, antimalarial, antimicrobial, antifungal, steroid antagonist, and enzyme inhibition, among others, aimed at furnishing pertinent insights for the future design of more potent and selective drugs.\u0000<img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-152-graphical-abstract.png?max-width=550' border='0'/>\u0000Beilstein J. Org. Chem. 2024, 20, 1713–1745. doi:10.3762/bjoc.20.152","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"140 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784069","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

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations 化学酶法全合成：实现化学和酶转化一体化的当前方法

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-23 DOI: 10.3762/bjoc.20.151

Ryo Tanifuji, Hiroki Oguri

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A fiber-optic spectroscopic setup for isomerization quantum yield determination 用于测定异构化量子产率的光纤光谱装置

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-22 DOI: 10.3762/bjoc.20.150

Anouk Volker, Jorn D. Steen, Stefano Crespi

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Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ3-iodanes 使用 N-杂环稳定λ3-碘烷将苄醇氧化为羰基化合物

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-19 DOI: 10.3762/bjoc.20.149

Thomas J. Kuczmera, Pim Puylaert, Boris J. Nachtsheim

引用次数: 0

Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes 将光生氮杂环丁烷醇开环作为合成氨基二氧戊环的一种策略

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-19 DOI: 10.3762/bjoc.20.148

Henning Maag, Daniel J. Lemcke, Johannes M. Wahl

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Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry 来自 RiPP 途径的甲基转移酶：塑造天然产物化学的景观

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-18 DOI: 10.3762/bjoc.20.147

Maria-Paula Schröder, Isabel P.-M. Pfeiffer, Silja Mordhorst

{"title":"Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry","authors":"Maria-Paula Schröder, Isabel P.-M. Pfeiffer, Silja Mordhorst","doi":"10.3762/bjoc.20.147","DOIUrl":"https://doi.org/10.3762/bjoc.20.147","url":null,"abstract":"Abstract\u0000This review article aims to highlight the role of methyltransferases within the context of ribosomally synthesised and post-translationally modified peptide (RiPP) natural products. Methyltransferases play a pivotal role in the biosynthesis of diverse natural products with unique chemical structures and bioactivities. They are highly chemo-, regio-, and stereoselective allowing methylation at various positions. The different possible acceptor regions in ribosomally synthesised peptides are described in this article. Furthermore, we will discuss the potential application of these methyltransferases as powerful biocatalytic tools in the synthesis of modified peptides and other bioactive compounds. By providing an overview of the various methylation options available, this review is intended to emphasise the biocatalytic potential of RiPP methyltransferases and their impact on the field of natural product chemistry.\u0000<img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-147-graphical-abstract.png?max-width=550' border='0'/>\u0000Beilstein J. Org. Chem. 2024, 20, 1652–1670. doi:10.3762/bjoc.20.147","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141742224","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}

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New triazinephosphonate dopants for Nafion proton exchange membranes (PEM) 用于纳菲昂质子交换膜（PEM）的新型三嗪膦酸盐掺杂剂

IF 2.7 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2024-07-17 DOI: 10.3762/bjoc.20.145

Fátima C. Teixeira, António P. S. Teixeira, C. M. Rangel

{"title":"New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)","authors":"Fátima C. Teixeira, António P. S. Teixeira, C. M. Rangel","doi":"10.3762/bjoc.20.145","DOIUrl":"https://doi.org/10.3762/bjoc.20.145","url":null,"abstract":"Abstract\u0000A new paradigm for energy is underway demanding decarbonized energy systems. Some of them rely on emerging electrochemical devices, crucial in hydrogen technologies, including fuel cells, CO2 and water electrolysers, whose applications and performances depend on key components such as their separators/ion-exchange membranes. The most studied and already commercialized Nafion membrane shows great chemical stability, but its water content limits its high proton conduction to a limited range of operating temperatures. Here, we report the synthesis of a new series of triazinephosphonate derivatives and their use as dopants in the preparation of new modified Nafion membranes. The triazinephosphonate derivatives were prepared by substitution of chlorine atoms in cyanuric chloride. Diverse conditions were used to obtain the trisubstituted (4-hydroxyphenyl)triazinephosphonate derivatives and the (4-aminophenyl)triazinephosphonate derivatives, but with these amino counterparts, only the disubstituted compounds were obtained. The new modified Nafion membranes were prepared by casting incorporation of the synthesized 1,3,5-triazinephosphonate (TPs) derivatives. The evaluation of the proton conduction properties of the new membranes and relative humidity (RH) conditions and at 60 °C, showed that they present higher proton conductivities than the prepared Nafion membrane and similar or better proton conductivities than commercial Nafion N115, in the same experimental conditions. The Nafion-doped membrane with compound TP2 with a 1.0 wt % loading showed the highest proton conductivity with 84 mS·cm−1.\u0000<img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-145-graphical-abstract.png?max-width=550' border='0'/>\u0000Beilstein J. Org. Chem. 2024, 20, 1623–1634. doi:10.3762/bjoc.20.145","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141719031","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