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Diamonds in Chemical Space: The Synthesis of Brexazine
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-12-05 DOI: 10.1002/hlca.202400175
Leon Rebhan, Ye Buehler, Jean-Louis Reymond
{"title":"Diamonds in Chemical Space: The Synthesis of Brexazine","authors":"Leon Rebhan,&nbsp;Ye Buehler,&nbsp;Jean-Louis Reymond","doi":"10.1002/hlca.202400175","DOIUrl":"https://doi.org/10.1002/hlca.202400175","url":null,"abstract":"<p>Here we searched chemical space for small and novel diamond-like, 3D-shaped building blocks, which are very rare but highly valuable for medicinal chemistry because they can increase the natural product likeness of drug molecules and improve their selectivity, water solubility and metabolism. We explored the Generated DataBases (GDBs), which list all possible organic molecules up to a defined size, identified 162 norbornane containing ring systems related to the known trinorbornane, and took inspiration from its simpler substructure brexane to design brexazine as a new chiral and 3D-shaped piperazine analog. The synthesis of brexazine was realized in 11 steps and 11.5 % overall yield from a commercially available norbornene building block. These experiments illustrate the value of exploring chemical space from first principles to design new building blocks for drug discovery.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143112008","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
Red-Shifted Bioluminescence Using Substrate-Fluorophore Conjugates
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-12-05 DOI: 10.1002/hlca.202400156
Clément Narbonne Zuccarelli, José Laxio-Arenas, Francesco Russo, Nicolas Winssinger
{"title":"Red-Shifted Bioluminescence Using Substrate-Fluorophore Conjugates","authors":"Clément Narbonne Zuccarelli,&nbsp;José Laxio-Arenas,&nbsp;Francesco Russo,&nbsp;Nicolas Winssinger","doi":"10.1002/hlca.202400156","DOIUrl":"https://doi.org/10.1002/hlca.202400156","url":null,"abstract":"<p>NanoLuc (NLuc) is one of the brightest luciferases and has been used in numerous reporter assays and sensor designs. However, its blue light emission (460 nm) is suboptimal for deep tissue imaging or some diagnostic application, and red shifting its emission is desirable. Here, we report the design and synthesis of novel furimazine and coelenterazine analogs conjugated with fluorophores to achieve red-shifted bioluminescence with NLuc and closely related H-Luc via a bioluminescence resonance energy transfer (BRET). Structural insights into NLuc-substrate interactions informed the functionalization of substrates. We report the synthesis of novel substrate-fluorophore conjugates. We show that red-shifted emission was achieved with high BRET ratios. The conjugates are less bright than the parent substrates, but our study highlights the importance of linker length and flexibility for optimizing bioluminescence emission reaching wavelength beyond 600 nm.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143112009","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
Interactions and Click Functionalization of a Poly(Thiophenyl-Tetrazine-Co-Fluorene) Conjugated Polymer with Single-Walled Carbon Nanotubes
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-12-04 DOI: 10.1002/hlca.202400146
Shagana Kukendran, Sara Salimi, Alex Adronov
{"title":"Interactions and Click Functionalization of a Poly(Thiophenyl-Tetrazine-Co-Fluorene) Conjugated Polymer with Single-Walled Carbon Nanotubes","authors":"Shagana Kukendran,&nbsp;Sara Salimi,&nbsp;Alex Adronov","doi":"10.1002/hlca.202400146","DOIUrl":"https://doi.org/10.1002/hlca.202400146","url":null,"abstract":"<p>A highly soluble thiophene-based poly(tetrazine) polymer was prepared that can undergo inverse-electron-demand Diels-Alder (IEDDA) click reactions efficiently with different types of <i>trans</i>-cyclooctene (TCO) derivatives resulting in post-polymerization functionalization. The resulting pyridazines post-oxidation exhibited strong interactions with single-walled carbon nanotubes (SWNTs) and showed selectivity toward metallic SWNTs. The resulting dispersions were used to prepare thin films, whose sheet resistivity was measured. It was found that α-amino-ω-methoxy triethylene glycol (TEG) functionalized pyridazine dispersion film resulted in a lower sheet resistance by several orders of magnitude compared to the non-clicked tetrazine dispersion indicating better conductivity post-IEDDA. Furthermore, modification of the polymer backbone while bound to the SWNT was performed successfully, preserving the properties of the nanotubes.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 2","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400146","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423572","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
Photoinduced Energy Transfer via an Atropisomeric Molecular Bridge
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-12-04 DOI: 10.1002/hlca.202400163
Dominik Lotter, Annika Huber, Joël Wellauer, Oliver S. Wenger, Christof Sparr
{"title":"Photoinduced Energy Transfer via an Atropisomeric Molecular Bridge","authors":"Dominik Lotter,&nbsp;Annika Huber,&nbsp;Joël Wellauer,&nbsp;Oliver S. Wenger,&nbsp;Christof Sparr","doi":"10.1002/hlca.202400163","DOIUrl":"https://doi.org/10.1002/hlca.202400163","url":null,"abstract":"<p>Atropisomeric scaffolds offer the possibility to predictably position donor and acceptor groups in specific spatial relationships. Herein, a configurationally stable 1,2’-binaphthyl linkage was employed to place a ruthenium(II) tris-(2,2’-bipyridine) complex in proximity to an anthracene moiety to explore how photoinduced triplet-triplet energy transfer can proceed across this type of molecular bridge. An efficient synthesis provided the ruthenium(II)-anthracene dyad with high yields, which allowed to determine characteristic features for the intramolecular energy transfer.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"108 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400163","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143111742","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
Radical C4−H Arylation of 1,4-Dihydropyridines with Cyanoarenes 1,4-二氢吡啶与氰芳烃的自由基C4−H芳基化反应
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-11-20 DOI: 10.1002/hlca.202400162
Huaixuan Guo, Shiqin Qiu, Peng Xu
{"title":"Radical C4−H Arylation of 1,4-Dihydropyridines with Cyanoarenes","authors":"Huaixuan Guo,&nbsp;Shiqin Qiu,&nbsp;Peng Xu","doi":"10.1002/hlca.202400162","DOIUrl":"https://doi.org/10.1002/hlca.202400162","url":null,"abstract":"<p>4-Aryl-1,4-dihydropyridines are prevalent pharmacophores and versatile building blocks in medicinal and synthetic chemistry. Herein, we demonstrated a mechanistically distinct radical-radical cross-coupling approach to 4-aryl-1,4-dihydropyridines, via direct C4−H arylation of 1,4-dihydropyridines with readily available cyanoarenes. This mild protocol is initiated by the direct photoexcitation of 1,4-dihydropyridines, eliminating the need for expensive photocatalysts and enabling operation under ambient air conditions.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 12","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142861747","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
Cover Picture: (Helv. Chim. Acta 11/2024) 封面图片：（Helv.）
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-11-16 DOI: 10.1002/hlca.202471101
{"title":"Cover Picture: (Helv. Chim. Acta 11/2024)","authors":"","doi":"10.1002/hlca.202471101","DOIUrl":"https://doi.org/10.1002/hlca.202471101","url":null,"abstract":"<p>\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 11","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202471101","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142664879","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
The pKa of Water and the Fundamental Laws Describing Solution Equilibria: An Appeal for a Consistent Thermodynamic Pedagogy 水的 pKa 和描述溶液平衡的基本规律：呼吁采用一致的热力学教学法
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-11-13 DOI: 10.1002/hlca.202400103
Thomas L. Neils, Stephanie Schaertel, Todd P. Silverstein
{"title":"The pKa of Water and the Fundamental Laws Describing Solution Equilibria: An Appeal for a Consistent Thermodynamic Pedagogy","authors":"Thomas L. Neils,&nbsp;Stephanie Schaertel,&nbsp;Todd P. Silverstein","doi":"10.1002/hlca.202400103","DOIUrl":"https://doi.org/10.1002/hlca.202400103","url":null,"abstract":"<p>A recurring misconception in some textbooks and research papers has led to an abandonment of fundamental physical laws when describing a subset of acid-base equilibria, especially regarding the role of the solvent. In the specific case of the autoprotolysis of water, experiments and theoretical calculations prove that the <i>K</i><sub>w</sub> of water at 25 °C, 1.00×10<sup>−14</sup>, is identical to its acid ionization constant, <i>K</i><sub>a</sub>. Nevertheless, several articles have been published erroneously purporting to give theoretical proof that the <i>K</i><sub>a</sub> of water is 10<sup>−15.743</sup> (1.81×10<sup>−16</sup>) and that the <i>K</i><sub>a</sub> of the aqueous proton (hydronium ion) is 55.3 rather than 1.00. Here we argue that using the incorrect numbers has pedagogical implications beyond those of a simple error. Arguments for the incorrect <i>K<sub>a</sub></i> and p<i>K<sub>a</sub></i> values require a misapplication of Henry's law and violate long-standing methods that use Raoult's law and the conservation of matter to describe the behavior of solutions. As a result, chemistry students may be asked to accept one set of physical principles in one course and another set in another course. Here we argue for adherence to fundamental physical laws governing solution equilibria as applied to the autoprotolysis of water and all aqueous acid base equilibria.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 11","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400103","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142664954","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
Suppressing Inversion of a Chiral Polycyclic Aromatic Aza Monkey Saddle by Molecular Editing 通过分子编辑抑制手性多环芳香族氮杂环猴鞍的反转
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-11-04 DOI: 10.1002/hlca.202400158
Tobias Kirschbaum, Simone Felicia Ebel, Frank Rominger, Michael Mastalerz
{"title":"Suppressing Inversion of a Chiral Polycyclic Aromatic Aza Monkey Saddle by Molecular Editing","authors":"Tobias Kirschbaum,&nbsp;Simone Felicia Ebel,&nbsp;Frank Rominger,&nbsp;Michael Mastalerz","doi":"10.1002/hlca.202400158","DOIUrl":"https://doi.org/10.1002/hlca.202400158","url":null,"abstract":"<p>Chiral polycyclic aromatic hydrocarbons with monkey saddle topology are a fascinating class of negatively curved compounds. To make the monkey-saddles valuable building blocks for chirality-assisted synthesis (CAS) approaches, the inversion barriers between the two possible enantiomers need to be high enough to prevent interconversion under CAS conditions. By molecular editing, aza monkey saddles were converted to the corresponding chromene monkey saddles that are configurationally stable even at temperatures of 220 °C over a period of 47 days. Their structures were studied by single X-ray diffraction and enantiomers were separated to study the chiroptical properties. Furthermore, mechanistic assumptions of the formation of the chromene monkey saddles by DFT calculations are discussed.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 12","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400158","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860171","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
Total Synthesis of Tagitinins, Goyazensolide and Related Furanoheliangolides and their Covalent Interaction with Importin-5 (IPO5) Tagitinins 、Goyazensolide 和相关呋喃香葱内酯的全合成及其与导入素-5 (IPO5) 的共价相互作用
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-10-27 DOI: 10.1002/hlca.202400122
Weilong Liu, Rémi Patouret, Elsa Peev, Sofia Barluenga, Nicolas Winssinger
{"title":"Total Synthesis of Tagitinins, Goyazensolide and Related Furanoheliangolides and their Covalent Interaction with Importin-5 (IPO5)","authors":"Weilong Liu,&nbsp;Rémi Patouret,&nbsp;Elsa Peev,&nbsp;Sofia Barluenga,&nbsp;Nicolas Winssinger","doi":"10.1002/hlca.202400122","DOIUrl":"https://doi.org/10.1002/hlca.202400122","url":null,"abstract":"<p>Herein, we detail an extension of our research on the synthesis of a small library of furanoheliangolides and the characterization of the covalent interaction between goyazensolide and IPO5. Using a build-couple-pair strategy, we assembled a small library of germacrene-type lactones and diversified them into eight groups of structurally different analogues. The germacrene lactones were synthesized using Sonogashira coupling and Barbier-type macrocyclization, while the furanoheliangolides were further elaborated through gold-catalyzed transannulation followed by esterification. This synthetic approach enabled the generation of a goyazensolide alkyne-tagged cellular probe, which was used to identify the selective binding between goyazensolide and the oncoprotein importin-5 (IPO5). Mass spectrometry analysis of the proteolytic digest from the reaction between the goyazensolide probe and a recombinant IPO5 indicated a covalent engagement at Cys560 of IPO5, which was confirmed by site-directed mutagenesis.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 11","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400122","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665114","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
Electronic Structures of Late versus Early Transition Metal Imido Complexes from 15N-NMR Signatures 从 15N-NMR 信号看晚期过渡金属亚胺配合物与早期过渡金属亚胺配合物的电子结构
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-10-27 DOI: 10.1002/hlca.202400142
Yuya Kakiuchi, Christophe Copéret
{"title":"Electronic Structures of Late versus Early Transition Metal Imido Complexes from 15N-NMR Signatures","authors":"Yuya Kakiuchi,&nbsp;Christophe Copéret","doi":"10.1002/hlca.202400142","DOIUrl":"https://doi.org/10.1002/hlca.202400142","url":null,"abstract":"<p>Imido ligand is a ubiquitous motif in organometallic chemistry, serving roles spanning from ancillary ligands to reactive sites. The nature of M=N bond is highly depended on the metal centres and their d-electron configuration, with late transition metal (TM) imido complexes exhibiting contrasting features when compared to their early TM analogues. Envisioning to uncover general electronic descriptor for the nature of imido ligands, we computationally investigate the solid-state <sup>15</sup>N NMR signatures of late TM imido complexes with various central metals, geometries and d-electron counts, and compare them against these of the corresponding early TM systems. The spectroscopic signatures are mostly driven by the presence of filled, π-symmetry orbitals in late TM imido complexes, suggesting the development of high-lying π(M=N) and low-lying σ/σ<sup>*</sup>(M=N) orbitals. This contrasts with what is observed for the reported early TM systems, for which high-lying σ-type orbitals determine the NMR signature. Noteworthily, Ni- and Pd-imido complexes with formal d<sup>10</sup> configurations exhibit highly asymmetric nitrogen-15 NMR signature with extremely deshielded principal components, because of the presence of filled, high-lying antibonding π<sup>*</sup>(M=N) orbitals, consistent with their high reactivity. The sensitive response of <sup>15</sup>N NMR signature to the nature of metal sites further highlights that chemical shift is a useful reactivity descriptor.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 11","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400142","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665113","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
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