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Rapid Discovery of Guaiane-Type Sesquiterpenoids with Rare Ring Skeletons from Daphne aurantiaca using Molecular Networking Together with MS-DIAL and Self-Built Database 利用分子网络、MS-DIAL和自建数据库快速发现金牡丹稀有环骨架的瓜蓝型倍半萜类化合物
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c01969
Shu-Hui Dong, Zhi-Kang Duan, Mei-Ya Lian, Ming Bai, Xiao-Xiao Huang, Shao-Jiang Song
{"title":"Rapid Discovery of Guaiane-Type Sesquiterpenoids with Rare Ring Skeletons from Daphne aurantiaca using Molecular Networking Together with MS-DIAL and Self-Built Database","authors":"Shu-Hui Dong, Zhi-Kang Duan, Mei-Ya Lian, Ming Bai, Xiao-Xiao Huang, Shao-Jiang Song","doi":"10.1021/acs.joc.5c01969","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01969","url":null,"abstract":"Under the guidance of the approach that integrates molecular networking, MS-DIAL and self-built database, 11 undescribed guaiane-type sesquiterpenoids (<b>1</b>–<b>11</b>) along with four known analogs (<b>12</b>–<b>15</b>) were targeted and isolated from <i>Daphne aurantiaca</i>. Among these, dapurant <b>A</b>–<b>B</b> (<b>1</b>–<b>2</b>) were unusual guaiane-type sesquiterpenoid dimers consisting of two guaiane-type sesquiterpenoids with different ring skeletons, and dapurant <b>C</b>–<b>D</b> (<b>3</b>–<b>4</b>) represented rare chlorinated guaiacane-type sesquiterpenoids. Their chemical structures and configurations were established via NMR spectroscopy analysis, computer-assisted structure elucidation methods, density functional theory (DFT) NMR calculations with suitable analysis methods (custom DP4+ analysis, CP3 analysis, MAE<sub>ΔΔδ</sub>), DU8+, electron-capture detector, detection (EC)D calculations, Rh<sub>2</sub>(OCOCF<sub>3</sub>)<sub>4</sub>-induced ECD analysis along with semisynthesis method. The network pharmacology analysis prompted us to explore the cholinesterase inhibitory activity and anti-Aβ aggregation activity of the isolates <i>in vitro</i> and <i>in silico</i>. The bioactivity evaluation results highlighted the prospects of <b>1</b>, <b>13</b>, and <b>14</b> as novel categories of neurological agents.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261344","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Aminocatalytic 1,6-Addition of 2-Benzyl-3-furaldehyde to 3-Cyano-4-styrylcoumarins: A Dearomative Approach for the Synthesis of Furan–Coumarin Hybrids 氨基催化1,6加成2-苄基-3-呋喃醛至3-氰基-4-苯乙烯香豆素：呋喃-香豆素杂化物的脱芳香合成方法
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c01406
Aleksandra Topolska, Artur Przydacz, Lesław Sieroń, Anna Skrzyńska, Alberto Fraile, Jose Alemán, Łukasz Albrecht
{"title":"Aminocatalytic 1,6-Addition of 2-Benzyl-3-furaldehyde to 3-Cyano-4-styrylcoumarins: A Dearomative Approach for the Synthesis of Furan–Coumarin Hybrids","authors":"Aleksandra Topolska, Artur Przydacz, Lesław Sieroń, Anna Skrzyńska, Alberto Fraile, Jose Alemán, Łukasz Albrecht","doi":"10.1021/acs.joc.5c01406","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01406","url":null,"abstract":"In the manuscript, the application of temporary dearomatization of 2-benzyl-3-furaldehyde under aminocatalytic conditions in a 1,6-addition pathway is described. In such reaction setup catalytically generated dienamine derived from heteroaromatic aldehydes reacts with coumarin derivatives in 1,6-addition. Developed approach utilizes a catalytic system consisting of an aminocatalyst and an acidic cocatalyst, which is crucial for the reaction efficiency. The reaction displays a wide substrate scope generating target products containing furan and coumarin moieties.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"44 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261488","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Alternative Synthetic Route to Rilzabrutinib via an E-Configured Cyanoacrylic Acid Intermediate 通过e型氰基丙烯酸中间体合成利扎布替尼的替代路线
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c02058
Daibao Wei, Jinbo Guo, Fuqiang Zhu, Emmanuel Mintah Bonku, Changliang Sun, Peng Yang, Hongjian Qin, Jingshan Shen
{"title":"An Alternative Synthetic Route to Rilzabrutinib via an E-Configured Cyanoacrylic Acid Intermediate","authors":"Daibao Wei, Jinbo Guo, Fuqiang Zhu, Emmanuel Mintah Bonku, Changliang Sun, Peng Yang, Hongjian Qin, Jingshan Shen","doi":"10.1021/acs.joc.5c02058","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02058","url":null,"abstract":"In this manuscript, an alternative route of synthesis for making rilzabrutinib via amide formation was described. The two segments for the amide formation are pyrazolopyrimidine-piperidine <b>20</b> and E-cyanoacrylic acid <b>21</b>. The yield of <b>20</b> from Mitsunobu reaction was doubled compared with the existing route, and the Knoevenagel-derived <b>21</b> exhibited exclusive E-configuration. This route, in contrast to Sanofi’s medicinal chemistry route, avoids Z/E isomer separation, achieves a 20-fold increase in overall yield, and improves sustainability through transition-metal-free catalysis and chromatography-free intermediates purification.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"34 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261489","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Conformational Analysis of Helical Peptides Incorporating Azepane-Based β-Amino Acids Prepared by an Ultrasound-Assisted Method 超声辅助法制备含氮杂烷基β-氨基酸的螺旋肽的构象分析
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c01530
Ingyu Han, Chae Na Lim, Soo Hyuk Choi
{"title":"Conformational Analysis of Helical Peptides Incorporating Azepane-Based β-Amino Acids Prepared by an Ultrasound-Assisted Method","authors":"Ingyu Han, Chae Na Lim, Soo Hyuk Choi","doi":"10.1021/acs.joc.5c01530","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01530","url":null,"abstract":"We report the synthesis of <i>cis</i>-5-aminoazepane-4-carboxylic acid (<i>cis-</i>AAzC) and its conformational behavior in nontraditional helical peptides. An ultrasound-assisted reductive amination method improves chemical yields and reduces solvent usage compared with previous methods. Incorporation of <i>cis</i>-AAzC into unnatural peptides promotes the 11/9-helix in 1:1 α/β-peptides and the 12/10-helix in β-peptides with enhanced aqueous solubility. The circular dichroism and the crystal structure data for these peptides suggest that additional functionalization at the azepane moiety is tolerated without disrupting helical propensity.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261345","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
EvolvedComplexity as a Total Synthesis Assessment Metric: Strychnine as a Case Study of Scoring Functions 演化复杂性作为全合成评价指标：士的宁作为评分函数的案例研究
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-10 DOI: 10.1021/acs.joc.5c01393
Abbigayle E. Cuomo, John-Paul Webster, H. Ray Kelly, Sumon Sarkar, Yu Shee, Sanil Sreekumar, Haote Li, Frederic Buono, Victor S. Batista, Timothy R. Newhouse
{"title":"EvolvedComplexity as a Total Synthesis Assessment Metric: Strychnine as a Case Study of Scoring Functions","authors":"Abbigayle E. Cuomo, John-Paul Webster, H. Ray Kelly, Sumon Sarkar, Yu Shee, Sanil Sreekumar, Haote Li, Frederic Buono, Victor S. Batista, Timothy R. Newhouse","doi":"10.1021/acs.joc.5c01393","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01393","url":null,"abstract":"The selection of synthetic routes to a small molecule of interest is enabled by the use of various tools to assess the chemical complexity of a given intermediate. While prior approaches assess the intrinsic molecular complexity or the facility with which an intermediate can be synthesized, in this study, we introduce an alternative approach that tracks the progress toward the target structure in a given synthesis. A simple metric, EvolvedComplexity, was developed that compares the chemical similarity of a pair of molecules on the basis of the Tanimoto distance between chemical fingerprints. This complementary approach to assessing progress in the synthesis may prove to be a useful tool for planning synthetic routes and developing novel chemistries.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261346","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Synthesis of Indolo[2,1-a]isoquinolines via Intramolecular Tandem Radical Cyclization 分子内串联自由基环化无过渡金属合成吲哚[2,1-a]异喹啉
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-10 DOI: 10.1021/acs.joc.5c02099
Zhiming Feng, Chengming Wang
{"title":"Transition-Metal-Free Synthesis of Indolo[2,1-a]isoquinolines via Intramolecular Tandem Radical Cyclization","authors":"Zhiming Feng, Chengming Wang","doi":"10.1021/acs.joc.5c02099","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02099","url":null,"abstract":"Diversely functionalized indolo[2,1-<i>a</i>]isoquinolines were rapidly constructed by regioselective metal-free intramolecular tandem cyclization. Initial mechanistic studies revealed that a single electron transfer (SET) radical process was possibly involved.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"86 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261491","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
1,3-Dipolar Cycloaddition of Nitrile Imines to 2-Imino-thiazolo[3,2-a]pyrimidin-3-ones: Dipole-Initiated Thiazolone-Imidazolone Rearrangement. 腈亚胺与2-亚胺-噻唑[3,2-a]嘧啶-3-酮的1,3-偶极环加成：偶极引发的噻唑-咪唑酮重排。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-10 DOI: 10.1021/acs.joc.5c00670
Juliana V Petrova,Maria E Filkina,Yuri K Grishin,Vitaly A Roznyatovsky,Victor A Tafeenko,Mikhail S Nechaev,Bogdan I Ugrak,Tatyana Ya Dutova,Artemii M Savin,Arsenii Y Boldyrikhin,Maxim E Kukushkin,Elena K Beloglazkina
{"title":"1,3-Dipolar Cycloaddition of Nitrile Imines to 2-Imino-thiazolo[3,2-a]pyrimidin-3-ones: Dipole-Initiated Thiazolone-Imidazolone Rearrangement.","authors":"Juliana V Petrova,Maria E Filkina,Yuri K Grishin,Vitaly A Roznyatovsky,Victor A Tafeenko,Mikhail S Nechaev,Bogdan I Ugrak,Tatyana Ya Dutova,Artemii M Savin,Arsenii Y Boldyrikhin,Maxim E Kukushkin,Elena K Beloglazkina","doi":"10.1021/acs.joc.5c00670","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00670","url":null,"abstract":"The 1,3-dipolar cycloaddition of nitrile imines to thiazolo[3,2-a]pyrimidine imines featuring both endocyclic and exocyclic C═N bonds was first reported. This reaction resulted in the regio- and stereoselective attachment of two dipole moieties, accompanied by peculiar skeletal rearrangements within the thiazolone fragment. Any products of only dipole addition cannot be isolated. The observed reactivity was explained using DFT protocols to investigate the cyclization mechanism of nitrile imines with thiazolo[3,2-a]pyrimidines.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"39 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145254669","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Absolute Configuration of Key Intermediates and the Gram Scale Synthesis of Berotralstat and ent-Berotralstat 关键中间体的绝对构型及贝罗曲司他和正贝罗曲司他的克级合成
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-10 DOI: 10.1021/acs.joc.5c01685
Pravin L. Kotian, Satish Vadlakonda, Venkat Chintareddy, Minwan Wu, Weihe Zhang, Krishnan Raman, Paul A. Wiget, Y. S. Babu
{"title":"Absolute Configuration of Key Intermediates and the Gram Scale Synthesis of Berotralstat and ent-Berotralstat","authors":"Pravin L. Kotian, Satish Vadlakonda, Venkat Chintareddy, Minwan Wu, Weihe Zhang, Krishnan Raman, Paul A. Wiget, Y. S. Babu","doi":"10.1021/acs.joc.5c01685","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01685","url":null,"abstract":"Berotralstat (BCX-7353) is a potent plasma kallikrein inhibitor developed to prevent hereditary angioedema attacks. Initial racemic synthesis yielded limited quantities of the active (<i>R</i>)-enantiomer. To support clinical studies, a stereoselective synthetic route was developed. Key intermediates were isolated, and their stereochemistry confirmed via X-ray diffraction. These efforts enabled the scalable preparation of 16 g of berotralstat in 61% yield and nearly 1 g of its enantiomer in 23% yield─representing the first reported gram-scale synthesis of both compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261490","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Antioxidant Power of Vitexin and Isovitexin Against OOH Radicals: A Comparative Theoretical Investigation. 牡荆素与异牡荆素抗OOH自由基能力的理论比较研究。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-10 DOI: 10.1021/acs.joc.5c01680
Maciej Spiegel,Nino Russo
{"title":"Antioxidant Power of Vitexin and Isovitexin Against OOH Radicals: A Comparative Theoretical Investigation.","authors":"Maciej Spiegel,Nino Russo","doi":"10.1021/acs.joc.5c01680","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01680","url":null,"abstract":"The antioxidant activity of vitexin and isovitexin─flavonoids widely found in various plants and used in traditional medicine─has been theoretically evaluated against the OOH radical. Multiple reaction mechanisms, including hydrogen atom transfer, single electron transfer, and radical adduct formation, were considered. The study accounts for all species present in aqueous solution at physiological pH as well as in lipid-like environments. Both compounds exhibit similar antioxidant activities, with apparent rate constants of 1.45 × 103 M-1 s-1 for vitexin and 4.78 × 103 M-1 s-1 for isovitexin. Compared to Trolox, a commonly used reference compound, their radical scavenging capacities are slightly lower.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145254668","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
The Chemical Synthesis of Certain Therapeutically Significant Alkaloids in the Era of Sustainability 可持续性时代某些具有治疗意义的生物碱的化学合成。
IF 3.6 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-09 DOI: 10.1021/acs.joc.4c02072
Shu Xiao, , , Ping Lan, , , Lorenzo V. White, , , Xin-Ting Liang, , , Martin G. Banwell*, , and , Shen Tan, 
{"title":"The Chemical Synthesis of Certain Therapeutically Significant Alkaloids in the Era of Sustainability","authors":"Shu Xiao,&nbsp;, ,&nbsp;Ping Lan,&nbsp;, ,&nbsp;Lorenzo V. White,&nbsp;, ,&nbsp;Xin-Ting Liang,&nbsp;, ,&nbsp;Martin G. Banwell*,&nbsp;, and ,&nbsp;Shen Tan,&nbsp;","doi":"10.1021/acs.joc.4c02072","DOIUrl":"10.1021/acs.joc.4c02072","url":null,"abstract":"<p >This perspective details work undertaken within the authors’ laboratories that attempts to address at least some of the challenges associated with the development of industrially applicable total syntheses of the therapeutically significant alkaloids morphine, codeine, colchicine and galanthamine. A primary motivation for doing this derives from the significant threats emerging from the ongoing reliance on the natural sources (viz. plants) of these crucial, clinically deployed medicines. Beyond the need to simply develop abbreviated syntheses of these natural products are the requirements that the routes involved are not just time-efficient but also atom-economical and, as much as possible, employ sustainably-derived substrates, “green” reagents (or no reagents at all) and solvents. Operating under such constraints is discussed, as is the need to generate new biomass-derived platform molecules, especially nitrogen-containing ones for which there are few truly global sources at the present time.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 41","pages":"14333–14348"},"PeriodicalIF":3.6,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145246989","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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