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Heterodimeric diketopiperazine alkaloids from Penicillium expansum MA147 and their cytotoxicity. 扩张青霉 MA147 中的异二元二酮哌嗪生物碱及其细胞毒性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01245c
Jing Li, Jing Wang, Xi Zhou, Xiao-Qian Wu, Yan Li, Yi-Yun Yuan, Wen-Yu Lu, Ai-Lin Liang, Peng-Ju Xu, Wen-Xuan Wang
{"title":"Heterodimeric diketopiperazine alkaloids from <i>Penicillium expansum</i> MA147 and their cytotoxicity.","authors":"Jing Li, Jing Wang, Xi Zhou, Xiao-Qian Wu, Yan Li, Yi-Yun Yuan, Wen-Yu Lu, Ai-Lin Liang, Peng-Ju Xu, Wen-Xuan Wang","doi":"10.1039/d4ob01245c","DOIUrl":"https://doi.org/10.1039/d4ob01245c","url":null,"abstract":"<p><p>Four previously undescribed heterodimeric diketopiperazine alkaloids, expansines A-D, were identified from the solid rice medium fermented by <i>Penicillium expansum</i> MA147, along with one new resorcylic acid derivative and five known compounds. Their structures and relative/absolute configurations were elucidated by interpretation of their spectroscopic data, quantum chemical calculations, and chemical conversion. Some obtained compounds were evaluated for the cytotoxicity against a triple-negative breast cancer cell line MDA-MB-231, and expansine C showed an IC<sub>50</sub> value of 3.23 μM. In further mechanistic studies, we found that it might act by increasing the expression of ATP-binding cassette transporter A1 and reducing cellular cholesterol levels, suggesting its potential as a novel anti-cancer agent.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453680","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
A one-pot synthesis of 2,3-dihydrobenzofurans, benzofuran-2(3H)-ones, and indoles via a [4 + 1] annulation reaction of ortho-substituted para-quinone methides and bromonitromethane. 通过正交取代的对醌甲醚和溴硝基甲烷的[4 + 1]环化反应，一步合成 2,3-二氢苯并呋喃、苯并呋喃-2(3H)-酮和吲哚。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01369g
Amol T Savekar, Vishal B Karande, Dattatray G Hingane, Suresh B Waghmode
{"title":"A one-pot synthesis of 2,3-dihydrobenzofurans, benzofuran-2(3<i>H</i>)-ones, and indoles <i>via</i> a [4 + 1] annulation reaction of <i>ortho</i>-substituted <i>para</i>-quinone methides and bromonitromethane.","authors":"Amol T Savekar, Vishal B Karande, Dattatray G Hingane, Suresh B Waghmode","doi":"10.1039/d4ob01369g","DOIUrl":"https://doi.org/10.1039/d4ob01369g","url":null,"abstract":"<p><p>Under mild and metal-free reaction conditions, a facile one-pot synthesis of oxygen- and nitrogen-containing benzoheterocycles has been achieved through [4 + 1] annulation of <i>para</i>-quinone methides, followed by an oxidation/elimination sequence, efficiently synthesizing functionalized 2,3-dihydrobenzofuran, benzofuran-2(3<i>H</i>)-one, and indole derivatives in moderate to good yields (up to 72%). A novel functional group tolerant oxidative Nef reaction utilizes DDQ without a base.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453669","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
Visible light-induced cascade sulfonylation/annulation of ortho-allyloxy chalcones with sodium sulfinates for the synthesis of sulfonated chromane derivatives. 可见光诱导的正烯丙基查耳酮与硫酸钠的级联磺化/annulation，用于合成磺化铬烷衍生物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-14 DOI: 10.1039/d4ob01319k
Huimin Li, Wenli Sheng, Junmin Chen
{"title":"Visible light-induced cascade sulfonylation/annulation of <i>ortho</i>-allyloxy chalcones with sodium sulfinates for the synthesis of sulfonated chromane derivatives.","authors":"Huimin Li, Wenli Sheng, Junmin Chen","doi":"10.1039/d4ob01319k","DOIUrl":"https://doi.org/10.1039/d4ob01319k","url":null,"abstract":"<p><p>A visible-light-induced radical cascade reaction for the synthesis of structurally diverse sulfonated chromanes is described. The protocol involves the addition of sulfonyl radicals to <i>ortho</i>-allyloxy chalcones and intramolecular Michael addition reactions in the presence of eosin Y as a photocatalyst. Additionally, this protocol shows that it is also an effective method to construct seven-membered oxygen-containing heterocycles. The method features a wide substrate scope, the use of easily accessible materials and excellent functional group tolerance with high to excellent yields. Control experiments and mechanistic studies indicate that a visible light-induced radical cascade process is involved in the transformation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453706","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 and properties of thienonaphtho[bc]pyridines and thienonaphtho[bc]quinolines† 噻吩并萘并[bc]吡啶和噻吩并萘并[bc]喹啉的合成及其特性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-07 DOI: 10.1039/D4OB01023J
Arpine Vardanyan, Jonas Polkaehn, Marie-Louis Bauder, Alexander Villinger, Peter Ehlers and Peter Langer
{"title":"Synthesis and properties of thienonaphtho[bc]pyridines and thienonaphtho[bc]quinolines†","authors":"Arpine Vardanyan, Jonas Polkaehn, Marie-Louis Bauder, Alexander Villinger, Peter Ehlers and Peter Langer","doi":"10.1039/D4OB01023J","DOIUrl":"10.1039/D4OB01023J","url":null,"abstract":"<p >The incorporation of heteroatoms within polycyclic aromatic compounds has gained significant interest due to its potential to effectively alter the inherent physicochemical properties of compounds without the need for profound structural changes. We herein report the development of a modular synthesis of hitherto unknown thienonaphtho[<em>bc</em>]pyridines and thienonaphtho[<em>bc</em>]quinolines in very good yields by Brønsted acid mediated cycloisomerization, permitting selective access to two isomeric products that are isoelectronic to the parent dibenzopyrene. The photophysical and electrochemical properties of the desired compounds were extensively studied and further complemented by DFT calculations.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob01023j?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142379547","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Highly selective recognition of fluoride using a trapezoidal cage† 利用梯形笼高度选择性地识别氟化物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-04 DOI: 10.1039/D4OB01465K
Ruiye Wu, Caihong Mao, Feiying Ruan, Yan Cai and Xiaobo Hu
{"title":"Highly selective recognition of fluoride using a trapezoidal cage†","authors":"Ruiye Wu, Caihong Mao, Feiying Ruan, Yan Cai and Xiaobo Hu","doi":"10.1039/D4OB01465K","DOIUrl":"10.1039/D4OB01465K","url":null,"abstract":"<p >By using a trapezoidal cage (<strong>1</strong>), highly selective recognition of F<small><sup>−</sup></small> (<em>S</em> &gt; 1000) was achieved in highly competitive environments composed of a large excess of various common anions. Through NMR, fluorescence, UV-vis and HRMS studies, the binding behavior and binding affinity (<em>β</em><small><sub>2</sub></small> = ∼10<small><sup>7</sup></small> M<small><sup>−2</sup></small>) of 1 + F<small><sup>−</sup></small> are shown.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142379544","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 metal-binding amino acids. 合成金属结合氨基酸。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-04 DOI: 10.1039/d4ob01326c
Katherine E V Deck, William D G Brittain
{"title":"Synthesis of metal-binding amino acids.","authors":"Katherine E V Deck, William D G Brittain","doi":"10.1039/d4ob01326c","DOIUrl":"https://doi.org/10.1039/d4ob01326c","url":null,"abstract":"<p><p>The ability for amino acid residues to bind metals underpins the functions of metalloproteins to conduct a plethora of critical processes in living organisms as well as unnatural applications in the fields of catalysis, sensing and medicinal chemistry. The capability to access metal-binding peptides heavily relies on the ability to generate appropriate building blocks. This review outlines recently developed strategies for the synthesis of metal binding non-proteinogenic amino acids. The chemistries to access, as well as to incorporate these amino acids into peptides is presented herein.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142370284","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
One-pot synthesis of N-sulfonylamidines from N-acylsulfonamides enabled by a metal triflate-mediated nonhydrolytic N-deacylation† 通过金属三late 介导的非水解 N-脱酰基反应，从 N-酰基磺酰胺中一次性合成 N-磺酰胺。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-04 DOI: 10.1039/D4OB01296H
Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu and Dayong Sang
{"title":"One-pot synthesis of N-sulfonylamidines from N-acylsulfonamides enabled by a metal triflate-mediated nonhydrolytic N-deacylation†","authors":"Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu and Dayong Sang","doi":"10.1039/D4OB01296H","DOIUrl":"10.1039/D4OB01296H","url":null,"abstract":"<p >A triflate salt-catalyzed nonhydrolytic method for the deacylation of <em>N</em>-acylsulfonamides and subsequent one-pot condensation of the newly formed sulfonamides with <em>N</em>,<em>N</em>-dimethylformamide dimethyl acetal to provide <em>N</em>-sulfonylamidines is presented. A range of aliphatic and aromatic <em>N</em>-acylsulfonamides bearing various <em>N</em>-acyl groups such as acetyl, propionyl, butyrl, isobutyryl, octanoyl, benzoyl, 2-phenylacetyl, and sterically hindered pivaloyl are readily transformed into the corresponding <em>N</em>-sulfonylamidines in good to excellent yields. A variety of functional groups including halogeno, keto, nitro, cyano, hydroxyl, ether, and carboxylic ester are tolerated intact.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386469","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 N-heterocyclic compounds using N,N-dimethylacetamides as an electrophilic carbon source† 使用 N,N-二甲基乙酰胺作为亲电碳源合成 N-杂环化合物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-03 DOI: 10.1039/D4OB01417K
Dayoung Chun, Seok Beom Lee, Simin Chun, Seung Hyun Choi, Junhwa Hong, Honghui Lee, Jinwoo Lee and Suckchang Hong
{"title":"Synthesis of N-heterocyclic compounds using N,N-dimethylacetamides as an electrophilic carbon source†","authors":"Dayoung Chun, Seok Beom Lee, Simin Chun, Seung Hyun Choi, Junhwa Hong, Honghui Lee, Jinwoo Lee and Suckchang Hong","doi":"10.1039/D4OB01417K","DOIUrl":"10.1039/D4OB01417K","url":null,"abstract":"<p >In this study, N-heterocyclic compounds were synthesized using nitrogen-containing nucleophilic substrates and electrophilic carbon sources derived from <em>N</em>,<em>N</em>-dimethylacetamide (DMAc). Depending on the nucleophilic groups, N-heterocyclic compounds such as 4-quinazolinones, pyrrole-quinoxalines, and dihydro-benzothiadiazine dioxides were produced. Carbon, adjacent to the nitrogen in DMAc, was activated in the presence of FeCl<small><sub>3</sub></small>·6H<small><sub>2</sub></small>O and di-<em>t</em>-butyl peroxide (DTBP). This procedure was considered an economical synthetic method because it utilized iron catalysts and DMAc as an electrophilic carbon source and a solvent.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142363465","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 albumin unfolding and refolding cycle induced by a time-controlled pH jump. 由时间控制的 pH 值跃迁诱导的白蛋白展开和再折叠循环。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-03 DOI: 10.1039/d4ob01289e
Alessandra Del Giudice, Daniele Del Giudice, Emanuele Spatola, Valentina Alemanno, Luciano Galantini, Stefano Di Stefano
{"title":"An albumin unfolding and refolding cycle induced by a time-controlled pH jump.","authors":"Alessandra Del Giudice, Daniele Del Giudice, Emanuele Spatola, Valentina Alemanno, Luciano Galantini, Stefano Di Stefano","doi":"10.1039/d4ob01289e","DOIUrl":"https://doi.org/10.1039/d4ob01289e","url":null,"abstract":"<p><p>Given the intimate connection between the structure and function of biological macromolecules, the ability to temporally control their unfolding-refolding process enables temporal regulation over specific functionalities, potentially applicable in innovative domains, including the construction of protein-based actuators or programmable catalysis and drug release in complex biotechnological processes. We show here how a temporally controlled protein unfolding-refolding cycle can be coupled in time with programmed pH sequences achieved through the spontaneous decomposition of an activated carboxylic acid. Specifically, we illustrate this process at the molecular level using albumin, the most prevalent protein found in plasma, for which a temporary shift from native to unfolded forms is promoted using nitroacetic acid, able to undergo base-catalysed decarboxylation when solubilized in water solution. As detected by small angle X-ray scattering and intrinsic tryptophan fluorescence, starting from the protein in its native form, the acid addition triggers unfolding to a partially denatured state and a subsequent time-tunable pH rise with gradual refolding that recapitulates the intermediate steps detected at the same pH values by static acidification, fitting within a framework of full reversibility of the structural changes as a function of the protein protonation state. At the end of the pH jump, the native structure is fully recovered, making this method a chemical tool to achieve a complete protein conformational sequence programmed in the timeframe of minutes without further intervention.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142363531","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
Well-defined cobalt(ii)-catalyzed synthesis of perimidine derivatives via acceptorless dehydrogenative annulation† 在钴(II)催化下，通过无受体脱氢环化合成明确的包嘧啶衍生物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-10-03 DOI: 10.1039/D4OB01306A
Debjyoti Pal, Rajashri Sarmah, Avijit Mondal, Itu Mallick and Dipankar Srimani
{"title":"Well-defined cobalt(ii)-catalyzed synthesis of perimidine derivatives via acceptorless dehydrogenative annulation†","authors":"Debjyoti Pal, Rajashri Sarmah, Avijit Mondal, Itu Mallick and Dipankar Srimani","doi":"10.1039/D4OB01306A","DOIUrl":"10.1039/D4OB01306A","url":null,"abstract":"<p >The versatility of the perimidine moiety offers a rich playground for researchers in fields ranging from medical science to industrial chemistry. Herein, we describe the first Co-catalyzed synthesis of 2,3-dihydro-1<em>H</em>-perimidine <em>via</em> acceptorless dehydrogenative annulation (ADA). Apart from featuring benzyl alcohol having different functionalities, heteroaryl and aliphatic alcohols also provide good yields. Our catalytic protocol is also suitable for different fatty alcohols for furnishing perimidine derivatives, keeping distal unsaturation intact. Several kinetic and control tests were carried out in order to understand the reaction sequence.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142386474","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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