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Stereoselective synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides: solvent-free Lewis acid catalysis. 2-deoxy-2-bromo-hexopyrano-β-nucleosides 的立体选择性合成：无溶剂路易斯酸催化。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI: 10.1039/d4ob01788a
Norein Sakander, Qazi Naveed Ahmed
{"title":"Stereoselective synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides: solvent-free Lewis acid catalysis.","authors":"Norein Sakander, Qazi Naveed Ahmed","doi":"10.1039/d4ob01788a","DOIUrl":"https://doi.org/10.1039/d4ob01788a","url":null,"abstract":"<p><p>An expedient solvent-free synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides stereo- and regioselectively from protected glycals and unactivated nucleobases using cheaper and easily available reagent systems has been developed. The synthesis is mediated by a Lewis acid and is solvent-free. The substrate scope of the reaction was analysed with ether, ester and silyl-protected glycals as donors and different pyrimidine and purine bases were taken into consideration. This method further finds application in the synthesis of 2-deoxynucleosides.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724313","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
L-Amino acid ester as a biomimetic reducing agent for the reduction of unsaturated CC bonds. L-Amino acid ester 作为一种生物模拟还原剂，用于还原不饱和 CC 键。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI: 10.1039/d4ob01640h
Ji-Wei Ren, Qing-Hao Zhang, Cheng-Shuai Han, Huai-Xin Zhang, Ya-Bin Wang, Hai-Rui Shi, Jing-Hui Sun, Yin-Feng Han
{"title":"L-Amino acid ester as a biomimetic reducing agent for the reduction of unsaturated CC bonds.","authors":"Ji-Wei Ren, Qing-Hao Zhang, Cheng-Shuai Han, Huai-Xin Zhang, Ya-Bin Wang, Hai-Rui Shi, Jing-Hui Sun, Yin-Feng Han","doi":"10.1039/d4ob01640h","DOIUrl":"https://doi.org/10.1039/d4ob01640h","url":null,"abstract":"<p><p>The first example of an efficient protocol for the reduction of disubstituted methyleneindolinones, isoindigos and tetrasubstituted olefins for the synthesis of 3-substituted 2-oxindoles, dihydroisoindigos and tetrasubstituted ethane derivatives using an L-amino acid ester as an attractive biomimetic reducing agent has been developed. This new protocol has the advantages of mild reaction conditions without the need for any metal catalysts, a broad substrate scope (31 examples), excellent yields (90-98%) and good functional group tolerance, providing an operationally simple and practically useful methodology for reductive reactions. The L-amino acid derivative, which is cheap, nontoxic and easy to handle, serves as a new biomimetic reducing agent for use in organic chemistry, providing a novel and promising approach for future applications in reductive reactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724310","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, optical properties, and two-photon bioimaging evaluation of novel fluorescent cationic molecules with symmetrical long conjugated all-trans structures†
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-26 DOI: 10.1039/D4OB01429D
Qiong Huang, Zhi-Bin Cai, Sheng-Li Li, Li-Jun Chen, Qing Ye and Yu-Peng Tian
{"title":"Synthesis, optical properties, and two-photon bioimaging evaluation of novel fluorescent cationic molecules with symmetrical long conjugated all-trans structures†","authors":"Qiong Huang, Zhi-Bin Cai, Sheng-Li Li, Li-Jun Chen, Qing Ye and Yu-Peng Tian","doi":"10.1039/D4OB01429D","DOIUrl":"10.1039/D4OB01429D","url":null,"abstract":"<p >Five novel fluorescent molecules (<strong>PPy</strong>, <strong>BOPPy</strong>, <strong>CNPPy</strong>, <strong>BPPy</strong>, and <strong>BPIm</strong>), which possess symmetrical long conjugated all-<em>trans</em> structures and are capped with hydroxyethyl-bonded pyridinium or benzimidazolium cations, were designed, synthesized, and characterized by <small><sup>1</sup></small>H NMR, <small><sup>13</sup></small>C NMR, and HRMS. The systematic investigations of their linear and nonlinear optical properties in different solvents indicate that all the target compounds exhibit large Stokes shifts (71–152 nm) and four of them (<strong>PPy</strong>, <strong>CNPPy</strong>, <strong>BPPy</strong>, and <strong>BPIm</strong>) have satisfactory two-photon action cross-sections (45.2–112.4 GM in DMSO). The fluorescence stability experiments reveal that their fluorescence emission is insensitive within the biologically relevant pH range of 4.0–8.0, which may enable applications <em>in vivo</em> to be possible. Cytotoxicity assessments, together with one- and two-photon excited fluorescence imaging studies in live cells were performed to evaluate their application values in bioimaging. It is found that <strong>PPy</strong> is not only endowed with low cytotoxicity and good cell membrane permeability, but also shows bright intracellular fluorescence signals. The high comprehensive performance enables <strong>PPy</strong> to have a promising application prospect in living cell imaging.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 48","pages":" 9426-9438"},"PeriodicalIF":2.9,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142764875","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
Iron-catalyzed ligand-free diazidation of alkenes controlled by the ratio of TBHP to TMSN3. 铁催化的烯烃无配体重氮化反应受 TBHP 与 TMSN3 的比例控制。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-26 DOI: 10.1039/d4ob01698j
Hongzhou Yu, Xingyu Li, Shitong Tang, Qian He, Mengchen Jiang, Xinyue Li, Fang Fang, Guoyu Zhang
{"title":"Iron-catalyzed ligand-free diazidation of alkenes controlled by the ratio of TBHP to TMSN<sub>3</sub>.","authors":"Hongzhou Yu, Xingyu Li, Shitong Tang, Qian He, Mengchen Jiang, Xinyue Li, Fang Fang, Guoyu Zhang","doi":"10.1039/d4ob01698j","DOIUrl":"https://doi.org/10.1039/d4ob01698j","url":null,"abstract":"<p><p>The diazidation of alkenes through an iron-catalyzed, ligand-free system has been established, providing straightforward access to structurally vicinal diazides in good yields at room temperature with TMSN<sub>3</sub> as the azido source. The ratio of <sup><i>t</i></sup>BuOOH to TMSN<sub>3</sub> was essential for the reaction: one equivalent TMSN<sub>3</sub> was needed to react with <sup><i>t</i></sup>BuOOH to form HN<sub>3</sub> as a nucleophile in the reaction ultimately achieving the diazidation of alkenes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714879","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
Two fluorinases prioritized from protein families of fluorinase, SAM-dependent chlorinase and hydroxide adenosyltransferase. 从氟化酶、SAM 依赖性氯化酶和氢氧化物腺苷转移酶的蛋白质家族中优先选择了两种氟化酶。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-26 DOI: 10.1039/d4ob01638f
Kai He, Yue Yan, Shuting Feng, Pinmei Wang, Zhizhen Zhang, Nan Wang
{"title":"Two fluorinases prioritized from protein families of fluorinase, SAM-dependent chlorinase and hydroxide adenosyltransferase.","authors":"Kai He, Yue Yan, Shuting Feng, Pinmei Wang, Zhizhen Zhang, Nan Wang","doi":"10.1039/d4ob01638f","DOIUrl":"https://doi.org/10.1039/d4ob01638f","url":null,"abstract":"<p><p>Fluorinases represent the only known biological catalysts capable of forming carbon-fluorine bonds, but their slow catalytic rate limits their broader application. In this study, two fluorinases, FlA<sup><i>Sbac</i></sup> and FlA<sup><i>Pbac</i></sup>, were identified from a pool of 12 718 nonredundant proteins using a genome-mining approach, with FlA<sup><i>Sbac</i></sup> showing high catalytic activity. Both newly identified fluorinases contain a Phe50 residue in place of the Trp50 typically found in fluorinases. Structural and mutagenesis studies revealed that the Trp50 or Phe50 residue at this position is crucial for fluorinase activity. This work highlights the utility of genomic enzymology in expanding the repertoire of biocatalysts for fluorination chemistry.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714883","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 hydroxyfluoroalkylation of quinoxalin-2(1H)-ones with N-trifluoroethoxyphthalimide under catalyst-free conditions. 在无催化剂条件下，N-三氟乙氧基邻苯二甲酰亚胺在可见光诱导下对喹喔啉-2(1H)-酮进行羟基氟烷基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-26 DOI: 10.1039/d4ob01616e
Liting Liu, Jing Liu, Siqi Li, Mengfei Yang, Xia Zhao, Kui Lu
{"title":"Visible light induced hydroxyfluoroalkylation of quinoxalin-2(1<i>H</i>)-ones with <i>N</i>-trifluoroethoxyphthalimide under catalyst-free conditions.","authors":"Liting Liu, Jing Liu, Siqi Li, Mengfei Yang, Xia Zhao, Kui Lu","doi":"10.1039/d4ob01616e","DOIUrl":"https://doi.org/10.1039/d4ob01616e","url":null,"abstract":"<p><p>For the first time, we achieved visible light-induced direct C3-hydroxyfluoroalkylation of quinoxalin-2(1<i>H</i>)-ones using <i>N</i>-trifluoroethoxyphthalimide as the trifluoroethanol radical precursor, without the need for a photocatalyst. The metal-free and catalyst-free nature of this method makes it an efficient and environmentally friendly approach for synthesizing C3-hydroxyfluoroalkylated quinoxalin-2(1<i>H</i>)-ones.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714884","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
Asymmetric 'Clip-Cycle' synthesis of 3-spiropiperidines. 3-spiropiperidines 的不对称 "Clip-Cycle "合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-26 DOI: 10.1039/d4ob01608d
Saikiran Ravi, Christopher J Maddocks, Ian J S Fairlamb, William P Unsworth, Paul A Clarke
{"title":"Asymmetric 'Clip-Cycle' synthesis of 3-spiropiperidines.","authors":"Saikiran Ravi, Christopher J Maddocks, Ian J S Fairlamb, William P Unsworth, Paul A Clarke","doi":"10.1039/d4ob01608d","DOIUrl":"https://doi.org/10.1039/d4ob01608d","url":null,"abstract":"<p><p>3-Spiropiperidines can be synthesized in up to 87% yield and 96 : 4 er using a two step 'Clip-Cycle' approach. The 'Clip' stage of this method is based on efficient and highly <i>E</i>-selective cross metathesis of <i>N</i>-Cbz-protected 1-amino-hex-5-enes with a thioacrylate. This is followed by the 'Cycle' step, in which an intramolecular asymmetric aza-Michael cyclization is promoted by a chiral phosphoric acid catalyst.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714877","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
TFA-promoted (hetero)arylation/hydroxylation of quinoxaline-2-one derivatives with electron-rich aromatic compounds. TFA 促进喹喔啉-2-酮衍生物与富电子芳香化合物的（杂）芳基化/羟基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-26 DOI: 10.1039/d4ob00882k
Ramanna Jatoth, Kishan Gugulothu, Nidhi Ravi, Ranamalla Gayathri, Shravani Parehosahalli Chandrakumar, K Shiva Kumar
{"title":"TFA-promoted (hetero)arylation/hydroxylation of quinoxaline-2-one derivatives with electron-rich aromatic compounds.","authors":"Ramanna Jatoth, Kishan Gugulothu, Nidhi Ravi, Ranamalla Gayathri, Shravani Parehosahalli Chandrakumar, K Shiva Kumar","doi":"10.1039/d4ob00882k","DOIUrl":"https://doi.org/10.1039/d4ob00882k","url":null,"abstract":"<p><p>A metal- and solvent-free, one-pot and TFA-promoted method for the construction of hetero/aryl-substituted quinoxalin-2-ones, pyrazin-2(1<i>H</i>)-ones, and pyrimidin-4(3<i>H</i>)-ones is reported. This method involves the reaction of chloro-derivatives of nitrogen heterocycles with electron-rich arenes/heteroarenes, followed by hydroxylation. This protocol is easy to use, providing access to (hetero)aryl-substituted <i>N</i>-heterocycles in good yields.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714881","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 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines via [3 + 2] cycloaddition of di/trifluoroacetohydrazonoyl bromides and trifluoromethyl-substituted alkenes. 通过二/三氟乙酰基肼溴化物和三氟甲基取代的烯的 [3 + 2] 环加成法合成 3,5-双（氟烷基）吡唑/吡唑啉。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-25 DOI: 10.1039/d4ob01160k
Ruikang Wang, Peng Jin, Gaowang Yang, Ying Fan, Zuyu Bai, Danfeng Huang, Ke-Hu Wang, Junjiao Wang, Yulai Hu
{"title":"Synthesis of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines <i>via</i> [3 + 2] cycloaddition of di/trifluoroacetohydrazonoyl bromides and trifluoromethyl-substituted alkenes.","authors":"Ruikang Wang, Peng Jin, Gaowang Yang, Ying Fan, Zuyu Bai, Danfeng Huang, Ke-Hu Wang, Junjiao Wang, Yulai Hu","doi":"10.1039/d4ob01160k","DOIUrl":"10.1039/d4ob01160k","url":null,"abstract":"<p><p>An efficient [3 + 2] cycloaddition reaction of difluoromethyl or trifluoromethyl hydrazonoyl bromides with trifluoromethyl-substituted alkenes was investigated to produce a variety of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines in moderate to good yields. This protocol features obvious advantages such as easily available and stable substrates, step economy, gram-scalability and simple operation, providing a novel and practical method for the preparation of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142708558","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
Isolation and biomimetic synthesis of acylphloroglucinol meroterpenoids as anti-breast cancer agents from Dryopteris crassirhizoma. 从旱芹中分离并仿生合成作为抗乳腺癌药物的酰基氯葡萄糖苷醇经络萜类化合物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-11-25 DOI: 10.1039/d4ob01548g
Ping Hai, Zhiqiang Luo, Nie Chen, Huixia Fan, Xudong Wu, Yunqing He, Sihao Deng, Haiyan Jia, Yuan Gao, Jian Yang
{"title":"Isolation and biomimetic synthesis of acylphloroglucinol meroterpenoids as anti-breast cancer agents from <i>Dryopteris crassirhizoma</i>.","authors":"Ping Hai, Zhiqiang Luo, Nie Chen, Huixia Fan, Xudong Wu, Yunqing He, Sihao Deng, Haiyan Jia, Yuan Gao, Jian Yang","doi":"10.1039/d4ob01548g","DOIUrl":"10.1039/d4ob01548g","url":null,"abstract":"<p><p>Two new acylphloroglucinol-nerolidol meroterpenoids (APNMs) [(±)-1 and (±)-2], with a skeleton of mixed sesquiterpene and dimeric acylphloroglucinol biosynthetic origin, were isolated from the medicinal pteridophyte <i>Dryopteris crassirhizoma</i>. Inspired by the proposed biosynthetic pathway, we initially completed the biomimetic syntheses of eight optically active <i>Dryopteris</i> APNMs (1-8) in a one-pot domino reaction. The structures of APNMs 1-8 including their absolute configurations were unambiguously established by a combination of NMR analysis, ECD calculations, and synthetic methods. Furthermore, an underlying method based on NMR data to assign the stereochemistry of the long-chain alcohol moieties in APNMs was revealed. Anti-triple negative breast cancer (anti-TNBC), antifungal and antibacterial activities of the synthetic meroterpenoids were evaluated. All tested compounds exhibited cytotoxicity against TNBC cells MDA-MB-231 with IC<sub>50</sub> values in the range of 1.22-27.43 μM, with (-)-8 being the most potent antitumor agent (IC<sub>50</sub>: 0.48 μM; selectivity index: 32.04). This study resulted in the biomimetic synthesis of APNMs for the first time and positioned APNMs from <i>D</i>. <i>crassirhizoma</i> as a new class of promising candidates for the development of new anti-TNBC drugs.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142708555","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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