Beilstein Journal of Organic Chemistry最新文献_第8页

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA. 用于与preQ1 RNA共价连接的亲电拴拴preQ1类似物的合成。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-03-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.35

Laurin Flemmich, Ronald Micura

{"title":"Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA.","authors":"Laurin Flemmich, Ronald Micura","doi":"10.3762/bjoc.21.35","DOIUrl":"10.3762/bjoc.21.35","url":null,"abstract":"The preQ1 cIass-I riboswitch aptamer can utilize 7-aminomethyl-7-deazaguanine (preQ1) ligands that are equipped with an electrophilic handle for the covalent attachment of the ligand to the RNA. The simplicity of the underlying design of irreversibly bound ligand-RNA complexes has provided a new impetus in the fields of covalent RNA labeling and RNA drugging. Here, we present short and robust synthetic routes for such reactive preQ1 and (2,6-diamino-7-aminomethyl-7-deazapurine) DPQ1 ligands. The readily accessible key intermediates of preQ0 and DPQ0 (both bearing a nitrile moiety instead of the aminomethyl group) were reduced to the corresponding 7-formyl-7-deazapurine counterparts. These readily undergo reductive amination to form the hydroxyalkyl handles, which were further converted to the haloalkyl or mesyloxyalkyl-modified target compounds. In addition, we report hydrogenation conditions for preQ0 and DPQ0 that allow for cleaner and faster access to preQ1 compared to existing routes and provide the novel compound DPQ1.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"483-489"},"PeriodicalIF":2.2,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897656/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613200","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

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction. 交叉偶联反应合成n -乙酰基重氮嘧啶衍生物。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-03-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.36

Thomas Brandt, Pascal Lentes, Jeremy Rudtke, Michael Hösgen, Christian Näther, Rainer Herges

{"title":"Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction.","authors":"Thomas Brandt, Pascal Lentes, Jeremy Rudtke, Michael Hösgen, Christian Näther, Rainer Herges","doi":"10.3762/bjoc.21.36","DOIUrl":"10.3762/bjoc.21.36","url":null,"abstract":"Diazocines are photoswitches derived from azobenzenes by bridging the two phenyl rings in ortho position with a CH2CH2 group forming an eight membered (diazocine) ring. Diazocine is superior to most azobenzenes in almost all photophysical properties (switching efficiency, quantum yield, wavelengths etc.). The biggest advantage, especially in photopharmacology and when used in photoswitchable materials, is the inverted thermodynamic stability of the two switching states (isomers). The Z isomer is more stable than the E form. However, one disadvantage that it shares with the frequently used azobenzene is that the switching efficiency decreases sharply with increasing water content in the solvent. In a recently published paper, we reported that replacing one CH2 group in the bridge with NCOCH3 not only confers intrinsic water solubility, but also largely eliminates the problem of reduced switching efficiency in aqueous solutions. In order to investigate the chemistry of this promising photoswitch and to unlock further applications, we now investigate strategies for the synthesis of derivatives, which are based on cross-coupling reactions. Fourteen vinyl-, aryl-, cyano-, and amino-substituted diazocines were prepared via Stille, Suzuki, and Buchwald-Hartwig reactions. X-ray structures are presented for derivatives 1, 2 and 7.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"490-499"},"PeriodicalIF":2.2,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11897653/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143613109","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

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction. 1,5-二羰基化合物的反迈克尔反应的有机催化动力学分解。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-03-03 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.34

James Guevara-Pulido, Fernando González-Pérez, José M Andrés, Rafael Pedrosa

引用次数: 0

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions. 光化学：利用机械力来增强光化学反应。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-03-03 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.33

Francesco Mele, Ana Maria Constantin, Andrea Porcheddu, Raimondo Maggi, Giovanni Maestri, Nicola Della Ca', Luca Capaldo

引用次数: 0

Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2'-dibromobiphenyls. 2,2'-二溴联苯电化学合成环联芳基λ3-溴。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-27 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.32

Andrejs Savkins, Igors Sokolovs

引用次数: 0

New tandem Ugi/intramolecular Diels-Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives. 基于乙烯呋喃和1,3-丁二烯呋喃衍生物的新型串联Ugi/分子内diols - alder反应。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-26 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.31

Yuriy I Horak, Roman Z Lytvyn, Andrii R Vakhula, Yuriy V Homza, Nazariy T Pokhodylo, Mykola D Obushak

{"title":"New tandem Ugi/intramolecular Diels-Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives.","authors":"Yuriy I Horak, Roman Z Lytvyn, Andrii R Vakhula, Yuriy V Homza, Nazariy T Pokhodylo, Mykola D Obushak","doi":"10.3762/bjoc.21.31","DOIUrl":"10.3762/bjoc.21.31","url":null,"abstract":"A new tandem sequence involving the Ugi reaction and Diels-Alder [4 + 2] cycloaddition based on vinylfuran and 1,3-butadienylfuran derivatives was designed and studied. It was found that in the case of 3-(furan-2-yl)acrylaldehyde, a one-pot Ugi reaction and intramolecular Diels-Alder vinylarene (IMDAV) reaction leads to the formation of the insufficiently studied furo[2,3-f]isoindole derivatives. Ugi adducts formed from (E)-3-(furan-2-yl)acrylaldehyde, maleic acid monoanilide, isonitrile, and an amine spontaneously underwent the IMDAV reaction with a high level of stereoselectivity, leading to single pairs of enantiomers of 4,4a,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindole core in excellent yields. Under the same conditions, the (2E,4E)-5-(furan-2-yl)penta-2,4-dienal gives an Ugi adduct that undergoes the IMDA reaction without involving the furan core. The cycloaddition leads to the formation of 2,3,3a,4,5,7a-hexahydro-1H-isoindoles in high yields. The studied tandem Ugi and intramolecular Diels-Alder reactions allow high substituent variation in the named isoindoles.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"444-450"},"PeriodicalIF":2.2,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11878150/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555710","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

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages. 超越对称自组装和有效摩尔浓度：解锁功能酶模拟与强大的有机笼。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-24 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.30

Keith G Andrews

{"title":"Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages.","authors":"Keith G Andrews","doi":"10.3762/bjoc.21.30","DOIUrl":"10.3762/bjoc.21.30","url":null,"abstract":"The bespoke environments in enzyme active sites can selectively accelerate chemical reactions by as much as 1019. Macromolecular and supramolecular chemists have been inspired to understand and mimic these accelerations and selectivities for applications in catalysis for sustainable synthesis. Over the past 60+ years, mimicry strategies have evolved with changing interests, understanding, and synthetic advances but, ubiquitously, research has focused on use of a molecular \"cavity\". The activities of different cavities vary with the subset of features available to a particular cavity type. Unsurprisingly, without synthetic access to mimics able to encompass more/all of the functional features of enzyme active sites, examples of cavity-catalyzed processes demonstrating enzyme-like rate accelerations remain rare. This perspective will briefly highlight some of the key advances in traditional cavity catalysis, by cavity type, in order to contextualize the recent development of robust organic cage catalysts, which can exploit stability, functionality, and reduced symmetry to enable promising catalytic modes.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"421-443"},"PeriodicalIF":2.2,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11878132/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555654","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

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane. 揭示芳香性：吡唑、吡唑啉和三维碳硼烷的双重世界。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-21 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.29

Zahra Noori, Miquel Solà, Clara Viñas, Francesc Teixidor, Jordi Poater

{"title":"Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane.","authors":"Zahra Noori, Miquel Solà, Clara Viñas, Francesc Teixidor, Jordi Poater","doi":"10.3762/bjoc.21.29","DOIUrl":"10.3762/bjoc.21.29","url":null,"abstract":"A new series of o-carborane-fused pyrazoles has been recently successfully synthesized. This fusion was expected to create a hybrid 3D/2D aromatic system, combining the 3D aromaticity of o-carborane with the 2D aromaticity of pyrazole. However, while the boron cage retains its aromatic character, the pyrazole's aromaticity is lost. As a result, rather than forming o-carborane-fused pyrazoles, the synthesis yielded o-carborane-fused pyrazolines, which are non-aromatic. The limited overlap between the π molecular orbitals (MOs) of the planar heterocycle and the n + 1 MOs of the carborane prevents significant electronic delocalization between the two fused components. This contrasts with the fusion of pyrazole and benzene to form indazole, where both rings maintain their 2D aromaticity. Our findings demonstrate that the peripheral σ-aromaticity of carborane and the π-aromaticity of the heterocycle are orthogonal, making a true 3D/2D aromatic system unachievable. The carborane is highly aromatic, generating highly negative NICS values (-25 to -30 ppm). We have observed that these high NICS values extend to fused rings, leading to incorrect estimations of aromaticity. Therefore, relying solely on NICS can be misleading, and other computational indicators, along with experimental or structural data, should be used to accurately assess aromaticity.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"412-420"},"PeriodicalIF":2.2,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11849550/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143490438","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

Identification and removal of a cryptic impurity in pomalidomide-PEG based PROTAC. 聚马来度胺-聚乙二醇基PROTAC中一个隐性杂质的鉴定与去除。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-18 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.28

Bingnan Wang, Yong Lu, Chuo Chen

引用次数: 0

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation. 邻基参与和可能的远距离远基参与对o -糖基化的影响。

IF 2.2 4区化学

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-17 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.27

Rituparna Das, Balaram Mukhopadhyay

{"title":"The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation.","authors":"Rituparna Das, Balaram Mukhopadhyay","doi":"10.3762/bjoc.21.27","DOIUrl":"10.3762/bjoc.21.27","url":null,"abstract":"Stereoselective glycosylations are one of the most challenging tasks of synthetic glycochemists. The protecting building blocks on the glycosides contribute significantly in attaining the required stereochemistry of the resulting glycosides. Strategic installation of suitable protecting groups in the C-2 position, vicinal to the anomeric carbon, renders neighbouring group participation, whereas protecting groups in the distal C-3, C-4, and C-6 positions are often claimed to exhibit remote group participation with the anomeric carbon. Neighbouring group participation and remote group participation are being widely studied to help the glycochemists design the synthetic protocols for multistep synthesis of complex oligosaccharides and in turn, standardise the process of the glycosylation towards a particular stereochemical output. While neighbouring group participation has been quite effective in achieving the required stereochemistry of the produced glycosides, remote participation exhibits comparatively less efficacy in achieving complete stereoselectivity in the glycosylation reactions. Remote participation is a still highly debated topic in the scientific community. However, implementing the participating role of the remote groups in glycosylation reactions is widely practised to achieve better stereocontrol and to facilitate the formation of synthetically challenging glycosidic linkages.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"369-406"},"PeriodicalIF":2.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11849559/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143490435","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