Organic & Biomolecular Chemistry最新文献

Chemoselective annulation of a tropolone linchpin enables divergent total syntheses of algicidal roseobacticides. tropolone关键蛋白的化学选择性环化使灭藻玫瑰杆菌剂的不同总合成成为可能。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01489e

Shuxin Yang, Niraj Aryal, Adam W E Stewart, Laura Burchill, Felipe M Quintana, Bryndan P Durham, Spencer J Williams

引用次数: 0

Recent advances in transition-metal-catalyzed N-formylation of amines with sustainable C1 sources. 过渡金属催化具有可持续C1源的n-甲酰化胺的最新进展。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01236a

Ketan Maru, Monak Patel

{"title":"Recent advances in transition-metal-catalyzed N-formylation of amines with sustainable C1 sources.","authors":"Ketan Maru, Monak Patel","doi":"10.1039/d6ob01236a","DOIUrl":"https://doi.org/10.1039/d6ob01236a","url":null,"abstract":"Formamides are indispensable intermediates in the synthesis of pharmaceuticals, agrochemicals, and functional materials. Yet, their conventional preparation relies on toxic stoichiometric reagents, including acetic formic anhydride, formyl chloride, and chloral, resulting in poor atom economy and substantial waste generation. Transition-metal catalysis has emerged as a sustainable alternative, enabling direct N-formylation of amines using renewable C1 feedstocks under mild conditions. This review summarizes advances reported from 2019 to 2026, covering six major C1 sources: carbon dioxide, methanol, biomass-derived carbonyl compounds (glycolic acid, glycerol derivatives, and oxalic acid), formic acid, paraformaldehyde, and triethyl orthoformate. Recent homogeneous manganese-, iron-, and copper-based systems for CO2 utilization, together with heterogeneous cobalt-based metal-organic frameworks and Co(II)-embedded covalent organic framework photocatalysts, demonstrate the expanding scope of catalytic N-formylation. This review critically evaluates mechanistic pathways involving carbamate and formamide intermediates, cobalt-formate species, silyl formates, oxidative C-C bond cleavage, and radical processes. By comparing catalyst architectures, C1-source characteristics, reaction conditions, mechanistic features, and sustainability considerations, this review identifies key structure-activity and selectivity trends and highlights emerging opportunities for the rational development of efficient, selective, recyclable, and sustainable N-formylation methodologies.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149219761","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

Late-stage electrosynthesis of sulfoxide metabolites from phenothiazine-based antipsychotic drugs. 以吩噻嗪为基础的抗精神病药物的亚砜代谢物的后期电合成。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01332e

Ridho Asra, Wesley R Browne, Louise Male, Alan M Jones

{"title":"Late-stage electrosynthesis of sulfoxide metabolites from phenothiazine-based antipsychotic drugs.","authors":"Ridho Asra, Wesley R Browne, Louise Male, Alan M Jones","doi":"10.1039/d6ob01332e","DOIUrl":"https://doi.org/10.1039/d6ob01332e","url":null,"abstract":"Phenothiazine (PTZ)-based antipsychotic drugs are extensively metabolised in vivo, with S-oxidation representing a major metabolic pathway. Herein, we report the application of an electrosynthetic (ES) S-oxidation strategy to three distinct classes of PTZ-based drug analogues: amino alkyl, piperidine, and piperazine-containing derivatives. The sulfoxide metabolites of the amino alkyl-containing PTZs, including chlorpromazine sulfoxide (2a, 68%), promazine sulfoxide (3a, 34%), triflupromazine sulfoxide (4a, 36%), and promethazine sulfoxide (5a, 11%), were generated under mild, constant-current conditions. For the piperidine-containing PTZs, electrooxidation of thioridazine (6) selectively afforded mesoridazine (7, 15%), while further S-oxidation of 7 at the PTZ ring system yielded the novel bis-sulfoxide 7a (3%). The piperazine-containing PTZs trifluoperazine (8) and fluphenazine (9) provided sulfoxide metabolites 8a (9%) and 9a (5%), alongside unprecedented ring-opened products 8b (1%) and 9b (2%) arising from electrochemical cleavage of the piperazine ring. Two distinct ring-opening mechanisms via decarboxylation (N-demethylation, Shono-type pathway) and via α-cleavage (neighbouring group participation) are proposed. Cyclic voltammetry confirmed successful S-oxidation through the characteristic disappearance of the first oxidation wave in all metabolite products. The methodology was further extended to thioether-containing active pharmaceutical ingredients (APIs) extracted from commercial dosage forms.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149222913","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 access to oxadibenzofused thiabicyclo[6.4.1]tridecen dioxides via K₂CO₃-mediated tandem C-/O-alkylative annulation of 1,3-diaroyl sulfones with o-bisbromomethyl arenes. 通过k2co3介导的1,3-二芳基砜与邻双溴甲基芳烃的串联C-/ o-烷基化环法制备氧二苯并噻吩[6.4.1]二十二氧化物。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01384h

Meng-Yang Chang, Yu-Hsuan Liu

引用次数: 0

Photoinduced C-Br bond cleavage enables difluoroketene-mediated ground-state [2 + 2] cycloaddition: a TD-DFT study. 光诱导C-Br键裂解使二氟烯烃介导的基态[2 + 2]环加成成为可能：一项TD-DFT研究。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob00958a

Cristian J Guerra, Leandro Ayarde-Henríquez, Oko Emmanuel Godwin, Hans Lenes, Efraín Polo-Cuadrado, Yeray A Rodríguez-Núñez, Adolfo E Ensuncho

{"title":"Photoinduced C-Br bond cleavage enables difluoroketene-mediated ground-state [2 + 2] cycloaddition: a TD-DFT study.","authors":"Cristian J Guerra, Leandro Ayarde-Henríquez, Oko Emmanuel Godwin, Hans Lenes, Efraín Polo-Cuadrado, Yeray A Rodríguez-Núñez, Adolfo E Ensuncho","doi":"10.1039/d6ob00958a","DOIUrl":"https://doi.org/10.1039/d6ob00958a","url":null,"abstract":"This work presents a TD-DFT computational study of the visible-light-driven [2 + 2] cycloaddition between alkynes and bromodifluoroacetylsilanes, leading to gem-difluorocyclobutenones. Visible-light irradiation of bromodifluoroacetylsilanes was recently shown by Zhou et al. to generate difluoroketene in situ for [2 + 2] cycloaddition with alkynes; the electronic origin of this photoactivation, however, had not been established. The results show that irradiation at 450 nm is vertically resonant only with the T1 triplet state of the brominated precursor, consistent with heavy-atom-enhanced spin-orbit coupling, although the specific population mechanism remains unresolved. On the triplet surface, barrierless C-Br homolysis generates an acyl radical and Br˙. We propose a SH2-type radical fragmentation mechanism in which the bromine radical attacks silicon, releasing difluoroketene through a low-barrier (ΔG‡ = 5.7 kcal mol-1) and highly exergonic process (ΔG = -25.0 kcal mol-1). The resulting difluoroketene subsequently undergoes a concerted, asynchronous, and barrier-moderate [π2s + π2s] cycloaddition with several alkynes on the ground-state surface (ΔG‡ ≈ 15.3-16.5 kcal mol-1), producing highly stable cyclobutenone products (ΔG ranging from -57.0 to -59.0 kcal mol-1). ELF analysis indicates a sequential bond-formation process initiated by nucleophilic attack at the electrophilic ketene carbonyl carbon. Overall, this study provides an electronic-structure and mechanistic analysis of photoexcitation, C-Br bond cleavage, silicon-mediated radical fragmentation, and ground-state ketene cycloaddition for this transformation, offering a computational basis to support the design of visible-light-driven fluorinated [2 + 2] cycloadditions.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149219745","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

The morphology of α-synuclein fibrils changes during formation, storage, and upon exposure to ligands. α-突触核蛋白原纤维的形态在形成、储存和暴露于配体时发生变化。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob00760k

Timothy S Chisholm

{"title":"The morphology of α-synuclein fibrils changes during formation, storage, and upon exposure to ligands.","authors":"Timothy S Chisholm","doi":"10.1039/d6ob00760k","DOIUrl":"https://doi.org/10.1039/d6ob00760k","url":null,"abstract":"Protein fibrils are pathological hallmarks of many neurodegenerative diseases, including Parkinson's disease. The preparation of α-synuclein (αSyn) fibrils in vitro is widely used in research relating to these conditions. However, αSyn fibrils exhibit substantial structural polymorphism. How fibril morphology evolves during formation, storage, or in the presence of small molecule ligands is poorly understood. Here, the evolution of αSyn fibril morphology was investigated using fluorescence assays, circular dichroism, transmission electron microscopy, and ligand profiling. Fibril morphology was found to evolve continuously during both aggregation of αSyn and subsequent storage, even at -79 °C. The inclusion of ligands, such as Thioflavin X, during aggregation affected both the reaction kinetics and the fibril morphologies formed. The addition of ligands to pre-formed fibrils also produced changes in fibril morphology. As different fibril morphologies exhibit distinct properties, more careful characterization and controls are required to ensure reproducibility and reliable interpretation of results. Additionally, these findings suggest the potential to use ligands to remodel fibril structure, possibly allowing for pathological morphologies to be converted to less pathological forms.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149219723","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

Accessing remote sulfonylated 8-aminoimidazo[1,2-a]pyridine derivatives: copper(II)-catalyzed synthesis, DFT calculations and docking studies. 获取远端磺化8-氨基咪唑[1,2-a]吡啶衍生物：铜（II）催化合成，DFT计算和对接研究。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01023g

Suman Kumar Joardar, Gunturu Prabhakar Rao, Jakkani Soumya, Soumen Dey, Sk Shamim Islam, Sohini Basu, Joydeep Ray, Arnab Roy, Mrinalkanti Kundu, Taraknath Kundu

{"title":"Accessing remote sulfonylated 8-aminoimidazo[1,2-a]pyridine derivatives: copper(II)-catalyzed synthesis, DFT calculations and docking studies.","authors":"Suman Kumar Joardar, Gunturu Prabhakar Rao, Jakkani Soumya, Soumen Dey, Sk Shamim Islam, Sohini Basu, Joydeep Ray, Arnab Roy, Mrinalkanti Kundu, Taraknath Kundu","doi":"10.1039/d6ob01023g","DOIUrl":"https://doi.org/10.1039/d6ob01023g","url":null,"abstract":"An efficient base-free approach for the remote C5-H sulfonylation of 8-aminoimidazo[1,2-a]pyridine (8-AIP) derivatives with sulfonyl chloride has been described under CuII-catalysis without an external oxidant. This strategy shows high conversion efficiency, a broad substrate scope, and good tolerance towards different functional groups. Furthermore, mechanistic investigations suggest that a single-electron-transfer process is involved in this C-S cross-coupling reaction. Considering that imidazopyridine derivatives and their analogues are known to be pharmacological agents for treating cancers through inhibition of the tankyrase-2 (TNKS-2) enzyme, docking studies were performed to understand the binding potential of our compounds to this protein, and the results revealed that several compounds had higher predicted binding energies than the crystal-bound ligand. Accordingly, our findings offer plausible mechanistic insights into the radical aromatic substitution of remote C-H bonds and open new avenues for the rational design of novel, drug-like molecules as potent TNKS-2 inhibitors.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149219674","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

Palladium-catalyzed synthesis of substituted 1,5-benzodiazocines and 1,5-benzooxazocines from bis-nucleophiles and an allylic dicarbonate. 钯催化双亲核试剂和烯丙基二碳酸酯合成取代1,5-苯并二氮杂嗪和1,5-苯并二氮杂嗪。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01372d

Masahiro Yoshida, Mai Yamashita, Touya Kariya, Shinya Shiomi

引用次数: 0

Enzymatic synthesis of sesterpenoids from iso-GFPP I, a geranylfarnesyl diphosphate analogue with a shifted double bond. 酶法合成具有移位双键的香叶基法尼基二磷酸类似物- isoggfpp I -酯类化合物。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-19 DOI: 10.1039/d6ob01353h

Heng Li, Jeroen S Dickschat

引用次数: 0

Visible-light-driven three-component cascade synthesis of perfluoroalkylated pyrimido[1,2-b]indazoles via EDA complexes. EDA配合物在可见光驱动下三组分级联合成全氟烷基化嘧啶[1,2-b]吲哚。

IF 2.8 3区化学

Organic & Biomolecular Chemistry Pub Date : 2026-10-16 DOI: 10.1039/d6ob01328g

Peng-Lu Liu, Dan-Dan Li, Qin-Hu Zhao, Zi-Wei Xi, Fu-Gang Zhao, Fei-Yong Xiang, Jian-Yu Cao, Ren-He Tang, Yong-Miao Shen

引用次数: 0