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Ammonium carboxylates in the ammonia-Ugi reaction: one-pot synthesis of α,α-disubstituted amino acid derivatives including unnatural dipeptides† 氨-乌基反应中的羧酸铵：α,α-二取代氨基酸衍生物（包括非天然二肽）的一次合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob00924j
{"title":"Ammonium carboxylates in the ammonia-Ugi reaction: one-pot synthesis of α,α-disubstituted amino acid derivatives including unnatural dipeptides†","authors":"","doi":"10.1039/d4ob00924j","DOIUrl":"10.1039/d4ob00924j","url":null,"abstract":"<div><p>Despite the remarkable developments of the Ugi reaction and its variants, the use of ammonia in the Ugi reaction has long been recognized as impractical and unsuccessful. Indeed, the ammonia-Ugi reaction often requires harsh reaction conditions, such as heating and microwave irradiation, and competes with the Passerini reaction, thereby resulting in low yields. This study describes a robust and practical ammonia-Ugi reaction protocol. Using originally prepared ammonium carboxylates in trifluoroethanol, the ammonia-Ugi reaction proceeded at room temperature in high yields and showed a broad substrate scope, thus synthesizing a variety of α,α-disubstituted amino acid derivatives, including unnatural dipeptides. The reaction required no condensing agents and proceeded without racemization of the chiral stereocenter of α-amino acids. Furthermore, using this protocol, we quickly synthesized a novel dipeptide, <span>d</span>-Leu-Aic-NH-CH<sub>2</sub>Ph(<em>p</em>-F), which exhibited a potent inhibitory activity against α-chymotrypsin with a <em>K</em><sub>i</sub> value of 0.091 μM.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob00924j?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141905073","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
Iron-catalyzed synthesis of substituted 3-arylquinolin-2(1H)-ones via an intramolecular dehydrogenative coupling of amido-alcohols† 通过氨基醇分子内脱氢偶联铁催化合成取代的 3-芳基喹啉-2(1H)-酮。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob00649f
{"title":"Iron-catalyzed synthesis of substituted 3-arylquinolin-2(1H)-ones via an intramolecular dehydrogenative coupling of amido-alcohols†","authors":"","doi":"10.1039/d4ob00649f","DOIUrl":"10.1039/d4ob00649f","url":null,"abstract":"<div><p>Here we report an iron-complex-catalyzed synthesis of various mono- and di-substituted quinolin-2(1<em>H</em>)-ones achieved <em>via</em> the intramolecular acceptorless dehydrogenative cyclization of amido-alcohols. This approach for the synthesis of N-heterocycles has provided access to underdescribed disubstituted quinolinones and represents an alternative to the well-known palladium-catalyzed coupling reactions.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141905077","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
Enantioselective Michael addition of 3-hydroxy-2-pyridone to nitroolefins using cinchona-derived bifunctional organocatalysts† 利用源自金鸡纳树的双功能有机催化剂，实现 3-羟基-2-吡啶酮与硝基烯烃的迈克尔对映选择性加成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01042f
{"title":"Enantioselective Michael addition of 3-hydroxy-2-pyridone to nitroolefins using cinchona-derived bifunctional organocatalysts†","authors":"","doi":"10.1039/d4ob01042f","DOIUrl":"10.1039/d4ob01042f","url":null,"abstract":"<div><p>Despite the extensive use of N-heteroarenes in pharmaceuticals and natural products, efficient methods for selective alkylation at the C-4 position of 2-pyridone are scarce. We developed an enantioselective Michael addition of 3-hydroxy-2-pyridone to nitroolefins at the C-4 position using cinchona-derived bifunctional squaramide organocatalysts, achieving up to 95% yield and &gt;99% ee. This selectivity is driven by the bifunctional organocatalysts’ hydrogen bonding interactions with 3-hydroxy-2-pyridone and nitroolefins under mild conditions. This method demonstrates the Michael reaction's versatility with various nitroolefins, providing a sustainable approach for synthesizing chiral N-heteroarenes with high enantioselectivity and regioselectivity under environmentally friendly conditions.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141974512","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
Transition metal-catalyzed transformations of 2-formylarylboronic acids 过渡金属催化的 2-甲酰基芳基硼酸转化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01024h
{"title":"Transition metal-catalyzed transformations of 2-formylarylboronic acids","authors":"","doi":"10.1039/d4ob01024h","DOIUrl":"10.1039/d4ob01024h","url":null,"abstract":"<div><p>2-Formylarylboronic acids are easily available precursors in organic chemistry. Different types of transition metal catalysts, such as Pd(0), Pd(<span>ii</span>), Rh(<span>i</span>), Ir(<span>i</span>), Ni(<span>ii</span>), Cu(<span>i</span>), Cu(<span>ii</span>), and Co(<span>ii</span>), can efficiently catalyze coupling reactions of 2-formylarylboronic acids with other organic reactants. In this review, we describe the synthesis of a diverse range of carbocyclic and heterocyclic compounds, as well as acyclic compounds, <em>via</em> transition metal-catalyzed reactions of 2-formylarylboronic acids over the past two decades.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141974514","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
Transition metal-free efficient synthesis of bis(indolyl)propynes (BIPs)† 双（吲哚基）丙炔（BIPs）的无过渡金属高效合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01017e
{"title":"Transition metal-free efficient synthesis of bis(indolyl)propynes (BIPs)†","authors":"","doi":"10.1039/d4ob01017e","DOIUrl":"10.1039/d4ob01017e","url":null,"abstract":"<div><p>A transition metal-free approach has been devised for the synthesis of a variety of bis(indolyl)propyne (BIP) derivatives. The strategy involves an iodine-catalyzed cascade condensation of α,β-unsaturated acetylenic aldehydes with diversely substituted indoles. The strategy was applicable to gram scale synthesis and a library of 50 molecules, which were afforded in good to excellent yields (up to 96%), was developed. The salient features of the reaction involve the synthesis of indole based privileged scaffolds in a short reaction time under transition metal-free conditions, with a wide substrate scope and excellent yields under ambient conditions.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981262","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
Dichlorotriazine-based multivalent probe for selective affinity labeling of carbohydrate-binding proteins† 基于二氯三嗪的多价探针，用于选择性亲和标记碳水化合物结合蛋白。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/D4OB01285B
Ayaka Tsuruno, Shione Kamoshita, Shoichi Hosoya and Kaori Sakurai
{"title":"Dichlorotriazine-based multivalent probe for selective affinity labeling of carbohydrate-binding proteins†","authors":"Ayaka Tsuruno, Shione Kamoshita, Shoichi Hosoya and Kaori Sakurai","doi":"10.1039/D4OB01285B","DOIUrl":"10.1039/D4OB01285B","url":null,"abstract":"<p >A new series of multivalent gold nanoparticle probes bearing different electrophilic groups were synthesized and their affinity labeling reactivities were evaluated. The dichlorotriazine group was identified as a useful protein-reactive label, allowing selective capture of a target protein at nanomolar probe concentrations.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142078519","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 anthracene-bridged expanded rosarin† 合成蒽键合膨松松香苷。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/D4OB01283F
Bharti Yadav and Mangalampalli Ravikanth
{"title":"Synthesis of anthracene-bridged expanded rosarin†","authors":"Bharti Yadav and Mangalampalli Ravikanth","doi":"10.1039/D4OB01283F","DOIUrl":"10.1039/D4OB01283F","url":null,"abstract":"<p >The newly synthesized precursor 1,8-di(1<em>H</em>-pyrrol-2-yl)anthracene was condensed with pentafluorobenzaldehyde under acid-catalyzed conditions to afford the first example of a unique anthracenyl-bridged rosarin. The X-ray structure revealed a coil-like arrangement of three dipyrromethene moieties and three anthracenyl units in the rosarin framework, which exhibits a weak fluorescence at 676 nm.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142078522","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
Iodine-promoted sequential C(sp3)–H oxidation and cyclization of aryl methyl ketones with 2-(2-aminophenyl)quinazolin-4(3H)-ones† 碘促进芳基甲基酮与 2-(2-氨基苯基)喹唑啉-4(3H)-酮的 C(sp3)-H 顺序氧化和环化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01146e
{"title":"Iodine-promoted sequential C(sp3)–H oxidation and cyclization of aryl methyl ketones with 2-(2-aminophenyl)quinazolin-4(3H)-ones†","authors":"","doi":"10.1039/d4ob01146e","DOIUrl":"10.1039/d4ob01146e","url":null,"abstract":"<div><p>An I<sub>2</sub>-promoted, metal-free protocol has been developed for the one-pot synthesis of 6-aroyl-5,6-dihydro-8<em>H</em>-quinazolino[4,3-<em>b</em>]quinazolin-8-ones from readily accessible substrates. This reaction involves the <em>in situ</em> sp<sup>3</sup> C–H oxidation of aryl methyl ketones to phenylglyoxal, followed by imine formation and intramolecular nucleophilic addition, resulting in the formation of two new C–N bonds. Furthermore, the method is applicable to a wide range of aryl methyl ketones, including heterocycles and drug-derived substrates, yielding the desired products with yields ranging from 62% to 93%. Additionally, the practical utility of this approach was demonstrated through gram-scale synthesis.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981260","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
Isoxazole group directed Rh(iii)-catalyzed alkynylation using TIPS-EBX† 使用 TIPS-EBX 进行异噁唑基团定向 Rh(III)- 催化炔化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob00797b
{"title":"Isoxazole group directed Rh(iii)-catalyzed alkynylation using TIPS-EBX†","authors":"","doi":"10.1039/d4ob00797b","DOIUrl":"10.1039/d4ob00797b","url":null,"abstract":"<div><p>A highly effective isoxazole directed <em>ortho</em> C–H alkynylation has been developed. Rhodium(<span>iii</span>) catalyzed direct di-(and/or mono) alkynylation using a hypervalent iodine reagent (TIPS-EBX) is reported. The reaction proceeds with a wide substrate scope under benign conditions. Preliminary mechanistic studies support this chelation assisted C–H alkynylation.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141557476","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
Dual SARS-CoV-2 and MERS-CoV inhibitors from Artemisia monosperma: isolation, structure elucidation, molecular modelling studies, and in vitro activities† 单叶蒿中的 SARS-CoV-2 和 MERS-CoV 双重抑制剂：分离、结构阐明、分子模型研究和体外活性。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob00929k
{"title":"Dual SARS-CoV-2 and MERS-CoV inhibitors from Artemisia monosperma: isolation, structure elucidation, molecular modelling studies, and in vitro activities†","authors":"","doi":"10.1039/d4ob00929k","DOIUrl":"10.1039/d4ob00929k","url":null,"abstract":"<div><p>The COVID-19 pandemic has spread throughout the whole globe, so it is imperative that all available resources be used to treat this scourge. In reality, the development of new pharmaceuticals has mostly benefited from natural products. The widespread medicinal usage of species in the Asteraceae family is extensively researched. In this study, compounds isolated from methanolic extract of <em>Artemisia monosperma</em> Delile, a wild plant whose grows in Egypt's Sinai Peninsula. Three compounds, stigmasterol 3-<em>O</em>-β-<span>d</span>-glucopyranoside <strong>1</strong>, rhamnetin <strong>3</strong>, and padmatin <strong>6</strong>, were first isolated from this species. In addition, five previously reported compounds, arcapillin <strong>2</strong>, jaceosidin <strong>4</strong>, hispidulin <strong>5</strong>, 7-<em>O</em>-methyleriodictyol <strong>7</strong>, and eupatilin <strong>8</strong>, were isolated. Applying molecular modelling simulations revealed two compounds, arcapillin <strong>2</strong> and rhamnetin <strong>3</strong> with the best docking interactions and energies within SARS-CoV-2 M<sup>pro</sup>-binding site (−6.16, and −6.70 kcal mol<sup>−1</sup>, respectively). The top-docked compounds (<strong>2–3</strong>) were further evaluated for inhibitory concentrations (IC<sub>50</sub>), and half-maximal cytotoxicity (CC<sub>50</sub>) of both SARS-CoV-2 and MERS-CoV. Interestingly, arcapillin showed high antiviral activity towards SARS-CoV-2 and MERS-CoV, with IC<sub>50</sub> values of 190.8 μg mL<sup>−1</sup> and 16.58 μg mL<sup>−1</sup>, respectively. These findings may hold promise for further preclinical and clinical research, particularly on arcapillin itself or in collaboration with other drugs for COVID-19 treatment.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141970080","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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