Helvetica Chimica Acta最新文献

TEMPS, the Chalcogen Cousin of the Infamous Stable Radical TEMPO, Traps Radicals via Substitution on Its Dimer (TEMPS)2 TEMPS是臭名昭著的稳定自由基TEMPO的表亲，通过在其二聚体（TEMPS）2上取代来捕获自由基

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-20 DOI: 10.1002/hlca.202500106

Felix Englmaier, Luke A. Farmer, Derek A. Pratt

{"title":"TEMPS, the Chalcogen Cousin of the Infamous Stable Radical TEMPO, Traps Radicals via Substitution on Its Dimer (TEMPS)2","authors":"Felix Englmaier, Luke A. Farmer, Derek A. Pratt","doi":"10.1002/hlca.202500106","DOIUrl":"https://doi.org/10.1002/hlca.202500106","url":null,"abstract":"Nitroxides such as 2,2,6,6-tetramethylpiperidin-N-oxyl (TEMPO) are the quintessential organic radicals. They are commonly used to trap alkyl radicals in controlled radical polymerizations, synthetic transformations and mechanistic experiments, and peroxyl radicals when applied as radical-trapping antioxidants (RTAs). Relatively little is known about their sulfur analogs (N-thiyl radicals, R2NS• and dithiobisamines, R2NS-SNR2). We found that dithiobisamines of moderate steric bulk (including (TEMPS)2, the dimer of the sulfur analog of TEMPO), trapped peroxyl radicals with rate constants up to 1.2 × 106 m−1s−1 (at 100 °C) – similar to TEMPO. Unlike TEMPO, their radical-trapping activity was not catalytic, independent of the rate of radical initiation and still operative in saturated hydrocarbons – implying a distinct mechanism. Additional experimental data and computations point to a homolytic substitution mechanism, analogous to that recently elucidated for tetrasulfides. In the absence of O2, alkyl radicals and dithiobisamines react to form sulfenamides, which may be exploited for synthetic purposes.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 9","pages":""},"PeriodicalIF":1.8,"publicationDate":"2025-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202500106","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145062740","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}

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Sascha Feldmann 萨沙的约

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-19 DOI: 10.1002/hlca.202500114

Sascha Feldmann

引用次数: 0

Ricardo J. Fernández-Terán 里卡多·费尔南德斯-特兰

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-14 DOI: 10.1002/hlca.202500112

Ricardo J. Fernández-Terán

引用次数: 0

Using High-Throughput Iridium-Catalyzed C─H Borylations for Rapid Investigation of Heterocyclic Fragments in Discovery Chemistry 用高通量铱催化C─H硼化反应快速研究发现化学中的杂环碎片

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-14 DOI: 10.1002/hlca.202500096

Clara Muller, Simone Kuhn, Sharon Bell, Richard Kraus, Thomas Stadelmann, Tomas Smejkal, Julien C. Vantourout, Daria Grosheva

{"title":"Using High-Throughput Iridium-Catalyzed C─H Borylations for Rapid Investigation of Heterocyclic Fragments in Discovery Chemistry","authors":"Clara Muller, Simone Kuhn, Sharon Bell, Richard Kraus, Thomas Stadelmann, Tomas Smejkal, Julien C. Vantourout, Daria Grosheva","doi":"10.1002/hlca.202500096","DOIUrl":"https://doi.org/10.1002/hlca.202500096","url":null,"abstract":"This study presents a workflow for rapidly assessing the applicability of Ir-catalyzed C─H borylation across structurally diverse heterocyclic fragments relevant to discovery chemistry. Leveraging cheminformatics, we have selected different N-containing bicyclic scaffolds and evaluated various reaction conditions via a high-throughput experimentation (HTE) platform. The diversified screening approach revealed suitable substrate-specific catalytic systems. The workflow integrates several key steps: 1) defining a focused subset of relevant heterocyclic scaffolds, 2) selecting structurally diverse scaffolds using clustering algorithms, 3) conducting HTE screening with multiple catalytic systems, and 4) scaling up promising hits in a high-throughput fashion. This approach enabled rapid exploration of reaction scope and identification of suitable conditions for various substrates. The study demonstrates the power of combining cheminformatics, HTE, and strategic experimental design to accelerate the evaluation and optimization of synthetic methodologies, with potential future implications for lead optimization in drug discovery and agrochemical development.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 9","pages":""},"PeriodicalIF":1.8,"publicationDate":"2025-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145062583","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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Mechanochemical and Piezo-Accelerated Stereoselective Synthesis of Isoindolinones 机械化学和压电加速立体选择性合成异吲哚酮

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-14 DOI: 10.1002/hlca.202500087

Amal Lakhal, Louis Fensterbank, Cyril Ollivier

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Repurposing FDA-Approved Anticancer Drugs Offers a Strategy to Target Mutant-Type Malaria by Inhibiting Parasite DHFR Without Affecting Human DHFR 重新利用fda批准的抗癌药物提供了一种通过抑制寄生虫DHFR而不影响人类DHFR来靶向突变型疟疾的策略

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-13 DOI: 10.1002/hlca.202500019

Sasipha Seetin, Patchreenart Saparpakorn, Thanaya Saeyang, Tararat Jantra, Jarunee Vanichtanankul, Danoo Vitsupakorn, Sumalee Kamchonwongpaisan, Supa Hannongbua

{"title":"Repurposing FDA-Approved Anticancer Drugs Offers a Strategy to Target Mutant-Type Malaria by Inhibiting Parasite DHFR Without Affecting Human DHFR","authors":"Sasipha Seetin, Patchreenart Saparpakorn, Thanaya Saeyang, Tararat Jantra, Jarunee Vanichtanankul, Danoo Vitsupakorn, Sumalee Kamchonwongpaisan, Supa Hannongbua","doi":"10.1002/hlca.202500019","DOIUrl":"https://doi.org/10.1002/hlca.202500019","url":null,"abstract":"Plasmodium falciparum dihydrofolate reductase-thymidylate synthase (PfDHFR-TS) is a well-defined antimalarial target of antifolate drugs. However, the emergence of parasite resistance to antifolate medications is the primary reason for the unsuccessful treatment of malaria. In this work, repurposing of anticancer drugs through virtual screening was conducted to identify critical interactions with quadruple type (qmPfDHFR-TS) and hDHFR (human dihydrofolate reductase). Three anticancer drugs-pralatrexate (PRA), pemetrexed (PME), and dasatinib (DAS) - exhibited significant binding interactions with qmPfDHFR-TS and hDHFR. The binding stability of PRA and the reference compound, P218, was determined using principal component analysis (PCA) and free energy landscape (FEL) analyses. Additionally, the key binding interaction patterns of qmPfDHFR-TS and hDHFR was further investigated through quantum chemical calculations. The PRA complex and P218 complex display meaningful H-bond interactions with Asp54, Arg59, and Arg122, as well as a π–π interaction with Phe58, in the qmPfDHFR-TS structure. For hDHFR, it was found that P218 and PRA do not establish H-bond interactions with Arg70, which is the conserved residue in hDHFR. Furthermore, this discovery was validated by conducting enzyme inhibition tests, which demonstrated the capacity of these compounds to inhibit PfDHFR enzymes. As a result, pralatrexate shows potential as an effective inhibitor against the mutant type of the PfDHFR enzyme.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 9","pages":""},"PeriodicalIF":1.8,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145062587","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 Properties of Cross-Shaped Polycyclic Aromatic Hydrocarbons 十字形多环芳烃的合成及性质

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-08-05 DOI: 10.1002/hlca.202500075

Junkai Huang, Lingyun Zhu, Taosong Wang, Ruiying Zhang, Yanxia Huang, Zi'ang Zhai, Yaohuan Mei, Lili Xie, Yuanming Li

引用次数: 0

Andreu Tortajada

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2025-07-31 DOI: 10.1002/hlca.202500103

Andreu Tortajada

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30 + 30 Stripes of Appreciation 30 + 30条欣赏条纹