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DNA aptamers for common buffer molecules: possibility of buffer interference in SELEX. 用于普通缓冲分子的DNA适配体：SELEX中缓冲干扰的可能性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-24 DOI: 10.1039/d4ob00622d
Yuzhe Ding, Ziyu Zhang, Yunus A Kaiyum, Yicheng Heng, Philip E Johnson, Juewen Liu
{"title":"DNA aptamers for common buffer molecules: possibility of buffer interference in SELEX.","authors":"Yuzhe Ding, Ziyu Zhang, Yunus A Kaiyum, Yicheng Heng, Philip E Johnson, Juewen Liu","doi":"10.1039/d4ob00622d","DOIUrl":"https://doi.org/10.1039/d4ob00622d","url":null,"abstract":"<p><p>During a typical aptamer selection experiment, buffer molecules are used at the 10 to 50 mM range, whereas target molecules could be used at much lower concentrations even in low μM levels. Therefore, doubts existed regarding the potential enrichment of buffer binding aptamers, particularly for failed selections that cannot validate binding of enriched sequences. In this study, we used two common buffer molecules, Tris and HEPES, as target molecules. While we successfully isolated aptamers for Tris buffer, our attempts to generate aptamers for HEPES buffer failed. Thioflavin T (ThT) fluorescence spectroscopy showed the dissociation constant (<i>K</i><sub>d</sub>) of the Tris buffer aptamer to be 2.9 mM, while isothermal titration calorimetry showed a <i>K</i><sub>d</sub> of 43 μM. NMR spectroscopy also confirmed aptamer binding. Finally, we discussed the implications of this buffer selection work and recommended the use of certain buffers.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306653","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Continuous flow synthesis of the antiviral drug tecovirimat and related sp3-rich scaffolds. 抗病毒药物替考韦瑞及相关富含 sp3 的支架的连续流合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-24 DOI: 10.1039/d4ob01379d
Arlene Bonner, Marcus Baumann
{"title":"Continuous flow synthesis of the antiviral drug tecovirimat and related sp<sup>3</sup>-rich scaffolds.","authors":"Arlene Bonner, Marcus Baumann","doi":"10.1039/d4ob01379d","DOIUrl":"https://doi.org/10.1039/d4ob01379d","url":null,"abstract":"<p><p>Herein we report a 2-step continuous flow synthesis of the antiviral drug tecovirimat, which is used for the treatment of monkeypox and smallpox. This work exploits a high-temperature pericyclic cascade process between cycloheptatriene and maleic anhydride generating a key sp<sup>3</sup>-rich scaffold, which affords the desired API after further condensation with an acyl hydrazide. Additional investigations of the key intermediate in reactions with different hydrazines revealed the accessibility of different heterocyclic chemotypes, depending on the substitution pattern of the hydrazine used. Ultimately, the streamlined and scalable access to these sp<sup>3</sup>-rich scaffolds enables improved access to tecovirimat and structurally related entities with high drug-like character.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Azide-based in situ preparation of fused heterocyclic imines and their multicomponent reactions. 基于叠氮化物的原位制备融合杂环亚胺及其多组分反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-24 DOI: 10.1039/d4ob01321b
Polina Paramonova, Rodion Lebedev, Alexander Sokolov, Dmitry Dar'in, Evgeny Kanov, Ramilya Murtazina, Raul Gainetdinov, Stanislav Kalinin, Olga Bakulina
{"title":"Azide-based <i>in situ</i> preparation of fused heterocyclic imines and their multicomponent reactions.","authors":"Polina Paramonova, Rodion Lebedev, Alexander Sokolov, Dmitry Dar'in, Evgeny Kanov, Ramilya Murtazina, Raul Gainetdinov, Stanislav Kalinin, Olga Bakulina","doi":"10.1039/d4ob01321b","DOIUrl":"https://doi.org/10.1039/d4ob01321b","url":null,"abstract":"<p><p>Structurally diverse pyrroles, indoles and imidazoles bearing an <i>N</i>-ω-azidoalkyl moiety and an aldehyde or ketone function were prepared and successfully introduced into <i>in situ</i> imine generation <i>via</i> the intramolecular Staudinger/aza-Wittig tandem reaction. Reduction of the generated imines led to medicinally relevant nitrogen-containing fused heterocycles such as tetrahydropyrrolo[1,2-<i>a</i>]pyrazines and diazepines. Rare 8-membered hexahydropyrrolo[1,2-<i>a</i>][1,4]diazocine and 9-membered dihydro-4,8-(metheno)pyrrolo[1,2-<i>a</i>][1,4]diazacycloundecine were also synthesized. In addition, several one-pot transformations involving cyclic anhydrides or isocyanides (Castagnoli-Cushman, Ugi and azido-Ugi reactions) were added to the Staudinger/aza-Wittig sequence to afford novel fused polyheterocyclic delta-lactams, cyclic bisamides and tetrazoles in a multicomponent fashion. The synthesized compounds were profiled against human Trace Amine-Associated Receptor 1 (hTAAR1), and the best performing compound showed low nanomolar agonistic activity with an EC<sub>50</sub> of 0.025 μM.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306651","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Synthesis of alkynyl cyclopropa[c]coumarins via propargyl sulfonium salts as C1 synthons. 通过丙炔基锍盐作为 C1 合剂合成炔基环丙[c]香豆素。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-24 DOI: 10.1039/d4ob01089b
Lavanya Chandrasekar, Yun-Zhen Hsieh, Hao-Tse Chou, Yu-Chen Huang, Wei-Min Liu
{"title":"Synthesis of alkynyl cyclopropa[<i>c</i>]coumarins <i>via</i> propargyl sulfonium salts as C1 synthons.","authors":"Lavanya Chandrasekar, Yun-Zhen Hsieh, Hao-Tse Chou, Yu-Chen Huang, Wei-Min Liu","doi":"10.1039/d4ob01089b","DOIUrl":"https://doi.org/10.1039/d4ob01089b","url":null,"abstract":"<p><p>Herein, we present a novel approach for the preparation of alkynyl cyclopropa[<i>c</i>]coumarin derivatives with medium to good yields utilizing propargyl sulfonium salts as C1 synthons. Compared with Br<sup>-</sup>, using ClO<sub>4</sub><sup>-</sup> as the counter anion significantly enhances the yield due to its lesser nucleophilic ability. This method features mild reaction conditions and a broad substrate scope with good diastereoselectivity when the substituted R<sup>1</sup> group is at the 5-position of the coumarin scaffold.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142306654","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
An electron donor-acceptor complex-initiated C-H trifluoromethylation and perfluoroalkylation of enamides and quinoxalinones. 由电子供体-受体复合物引发的烯酰胺和喹喔啉酮的 C-H 三氟甲基化和全氟烷基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-23 DOI: 10.1039/d4ob01228c
Yaqi Song, Tian-Yu Sun, Xiao-Feng Xia, Dawei Wang
{"title":"An electron donor-acceptor complex-initiated C-H trifluoromethylation and perfluoroalkylation of enamides and quinoxalinones.","authors":"Yaqi Song, Tian-Yu Sun, Xiao-Feng Xia, Dawei Wang","doi":"10.1039/d4ob01228c","DOIUrl":"https://doi.org/10.1039/d4ob01228c","url":null,"abstract":"<p><p>Facilitated by an electron donor-acceptor (EDA) complex, an efficient β-trifluoromethylation and perfluoroalkylation of enamides with Togni reagent or perfluoroalkyl iodides is presented under transition-metal-free, photocatalyst-free and mild reaction conditions. Notably, using this photocatalyst-free strategy, direct trifluoromethylation and perfluoroalkylation of quinoxalin-2(1<i>H</i>)-one derivatives was also achieved <i>via</i> a photoactive electron donor-acceptor complex.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277418","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Design strategy and preliminary antiproliferative investigation of a modified lignan skeleton derived from aryne and statin. 从芳香烃和他汀中提取的改良木质素骨架的设计策略和初步抗增殖研究。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-23 DOI: 10.1039/d4ob01264j
Yu Lei, Yinshan Wen, Xiaoliang Xu, Qiong Hu, Meng Chang, Ruihua Qiang, Yimin Hu
{"title":"Design strategy and preliminary antiproliferative investigation of a modified lignan skeleton derived from aryne and statin.","authors":"Yu Lei, Yinshan Wen, Xiaoliang Xu, Qiong Hu, Meng Chang, Ruihua Qiang, Yimin Hu","doi":"10.1039/d4ob01264j","DOIUrl":"https://doi.org/10.1039/d4ob01264j","url":null,"abstract":"<p><p>The biological activities of natural products (NPs) provided precious resources for the development of new drugs. Numerous studies have shown that statins exhibit cytotoxic potential, which is now an extensive focus of investigation. Herein, a remarkably efficient method for modification of statins using hexadehydro-Diels-Alder (HDDA) arynes has been described. Notably, lactone, as the biologically active group of statins, was removed during the reaction and a novel modified lignan skeleton was generated <i>via</i> the Alder-ene process. Unexpectedly, these statin-derived novel chemical scaffolds exhibited moderate inhibition effects on the proliferation of cancer cells as determined by CCK-8 assays, and the IC<sub>50</sub> values were in the micromolar range.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277421","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Copper-catalyzed tandem cyclization reaction of ethynylbenzoxazinones and thiols: facile construction of 2-thiomethylene indoles. 铜催化的乙炔基苯并恶嗪酮与硫醇的串联环化反应：2-硫代亚甲基吲哚的简易构建。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-23 DOI: 10.1039/d4ob01164c
Lei Song, Fu-Qiang Li, Xiao-Han Qiu, Guo-Zhen Wei, Hui-Yu Chen, Ming Bian, Yu-Ning Gao, Zhen-Jiang Liu
{"title":"Copper-catalyzed tandem cyclization reaction of ethynylbenzoxazinones and thiols: facile construction of 2-thiomethylene indoles.","authors":"Lei Song, Fu-Qiang Li, Xiao-Han Qiu, Guo-Zhen Wei, Hui-Yu Chen, Ming Bian, Yu-Ning Gao, Zhen-Jiang Liu","doi":"10.1039/d4ob01164c","DOIUrl":"https://doi.org/10.1039/d4ob01164c","url":null,"abstract":"<p><p>The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper-allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained. This methodology offers significant advantages including mild reaction conditions, cheap catalysts, good yields and broad substrate compatibility.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277419","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Synthesis of unsymmetrical 2,4-diaryl substituted and 3-bromo-2-(4-bromoalkoxy)-derived pyranocoumarins. 不对称 2,4-二芳基取代和 3-溴-2-(4-溴烷氧基)衍生吡喃香豆素的合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-23 DOI: 10.1039/d4ob01353k
Velu Saravanan, Pin-Hui Lin, Ding-Yah Yang
{"title":"Synthesis of unsymmetrical 2,4-diaryl substituted and 3-bromo-2-(4-bromoalkoxy)-derived pyranocoumarins.","authors":"Velu Saravanan, Pin-Hui Lin, Ding-Yah Yang","doi":"10.1039/d4ob01353k","DOIUrl":"https://doi.org/10.1039/d4ob01353k","url":null,"abstract":"<p><p>A series of unsymmetrical 2,4-disubstituted pyranocoumarins and 3-bromo-2-(4-bromoalkoxy)-derived pyranocoumarins were synthesized <i>via</i> the palladium-catalyzed C-H arylation of 4-phenyl-4<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromen-5-ones with aryl iodide and the three-component reaction of 4-phenyl-4<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromen-5-one with bromine and cyclic ether, respectively.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277426","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
gem-Difluoroallene (DFA): an emerging versatile synthetic precursor to enable diverse fluorinated molecules. gem-二氟甲苯 (DFA)：一种新兴的多功能合成前体，可生成多种氟化分子。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-23 DOI: 10.1039/d4ob01253d
Kota Sathish, Swati Jain, Naveen Sihag, M Ramu Yadav
{"title":"<i>gem</i>-Difluoroallene (DFA): an emerging versatile synthetic precursor to enable diverse fluorinated molecules.","authors":"Kota Sathish, Swati Jain, Naveen Sihag, M Ramu Yadav","doi":"10.1039/d4ob01253d","DOIUrl":"https://doi.org/10.1039/d4ob01253d","url":null,"abstract":"<p><p>Organofluorine compounds are increasingly found in diverse fields, such as pharmaceuticals, agrochemicals, and materials science. <i>gem</i>-Difluoroallenes, which have <i>gem</i>-difluoro alkenes and allenes-like properties, offer a distinct and adaptable platform for novel synthetic transformations. Their distinctiveness is highlighted by various strategies, where the <i>gem</i>-difluoro group's presence plays a pivotal role in successful reactions. This review article presents a comprehensive overview of the latest progress in utilizing <i>gem</i>-difluoroallenes for selective additions, defluorination, as well as cycloaddition and cyclization reactions. We also discuss the limitations and future directions in this area, inspiring further exploration and innovation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277413","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Unveiling the reactivity of 2H-(thio)pyran-2-(thi)ones in cycloaddition reactions with strained alkynes through density functional theory studies. 通过密度泛函理论研究揭示 2H-(硫)吡喃-2-(硫)-1 在与受约束炔烃的环加成反应中的反应性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-20 DOI: 10.1039/d4ob01263a
Wei Huang, Kangqiao Wen, Scott T Laughlin, Jorge Escorihuela
{"title":"Unveiling the reactivity of 2<i>H</i>-(thio)pyran-2-(thi)ones in cycloaddition reactions with strained alkynes through density functional theory studies.","authors":"Wei Huang, Kangqiao Wen, Scott T Laughlin, Jorge Escorihuela","doi":"10.1039/d4ob01263a","DOIUrl":"https://doi.org/10.1039/d4ob01263a","url":null,"abstract":"<p><p>Over the past two decades, click chemistry transformations have revolutionized chemical and biological sciences. Among the different strain-promoted cycloadditions, the inverse electron demand Diels-Alder reaction (IEDDA) has been established as a benchmark reaction. We have theoretically investigated the IEDDA reaction of <i>endo</i>-bicyclo[6.1.0]nonyne (<i>endo</i>-BCN) with 2<i>H</i>-pyran-2-one, 2<i>H</i>-thiopyran-2-one, 2<i>H</i>-pyran-2-thione and 2<i>H</i>-thiopyran-2-thione. These 2<i>H</i>-(thio)pyran-2-(thi)ones have displayed different reactivity towards <i>endo</i>-BCN. Density functional theory (DFT) calculations show, in agreement with experiments, that <i>endo</i>-BCN reacts significantly faster with 2<i>H</i>-thiopyran-2-one compared to other 2<i>H</i>-(thio)pyran-2-(thi)one derivatives because of the lower distortion energy. Experimentally determined second-order rate constants for the reaction of a 2<i>H</i>-pyran-2-thione with different strained derivatives, including a 1-methylcyclopropene derivative and several cycloalkynes (<i>exo</i>-BCN, (1<i>R</i>,8<i>S</i>)-bicyclo[6.1.0]non-4-yne-9,9-diyl)dimethanol, dibenzocycylooctyne and a light activatable silacycloheptyne, were used to validate the computational investigations and shed light on this reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142277427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
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