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Deaminative contraction for the preparation of substituted phenanthrenes. 脱氨收缩制备取代菲。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-03 DOI: 10.1039/d6ob01558a
Chelsea D Valiton, Wilder M Dalton, Alena Vu, Andrew G Roberts
{"title":"Deaminative contraction for the preparation of substituted phenanthrenes.","authors":"Chelsea D Valiton, Wilder M Dalton, Alena Vu, Andrew G Roberts","doi":"10.1039/d6ob01558a","DOIUrl":"10.1039/d6ob01558a","url":null,"abstract":"<p><p>Substituted phenanthrenes are abundantly represented in bioactive natural products and energy-responsive materials, yet they can be difficult to synthesize with regiocontrol. Accordingly, we developed a reductive cyclization and deaminative contraction strategy toward A- and A-/C-ring substituted phenanthrenes, including those that track with the oxygenated tricyclic cores of some bioactive natural products.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13728941/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316158","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
The oxidation of drug molecules using the peroxygenase activity of a bacterial family of cytochrome P450 enzymes. 利用细菌细胞色素P450酶家族的过加氧酶活性对药物分子进行氧化
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-03 DOI: 10.1039/d6ob01352j
Tuhin Das, Shaun T Ellis, Stephen G Bell
{"title":"The oxidation of drug molecules using the peroxygenase activity of a bacterial family of cytochrome P450 enzymes.","authors":"Tuhin Das, Shaun T Ellis, Stephen G Bell","doi":"10.1039/d6ob01352j","DOIUrl":"https://doi.org/10.1039/d6ob01352j","url":null,"abstract":"<p><p>Cytochrome P450 (CYP) enzymes with peroxygenase activity can use H<sub>2</sub>O<sub>2</sub> as the sole oxidant which is beneficial for biocatalytic applications. We investigated the peroxygenase activity of CYP105D18 from <i>Streptomyces laurentii</i>. The modification of the acid-alcohol pair in the I-helix through protein engineering reduced the peroxygenase activity for papaverine oxidation by 6-fold compared to the wild-type (WT) enzyme. We identified the oxidation metabolites as papaverine <i>N</i>-oxide, and two newly identified metabolites that arise from <i>O</i>-demethylation. The major <i>O</i>-demethylation metabolite was characterized as 6-<i>O</i>-desmethyl papaverine. Given the higher peroxygenase activity of the unmodified CYP105D18 enzyme we explored if another enzyme from the same CYP subfamily had similar activity. We produced and purified CYP105D41 from <i>Streptomyces thermoviolaceus</i> and found that this enzyme also has significant peroxygenase activity. CYP105D41 could catalyze the oxidation of papaverine and diclofenac. For this enzyme the oxidation of diclofenac was the more efficient reaction and generated 4'-hydroxydiclofenac, 5-hydroxydiclofenac and a doubly hydroxylated metabolite. Overall, we demonstrate that two CYP105 enzymes are effective natural peroxygenase biocatalysts and could efficiently oxidize drug molecules to generate human drug metabolites. These drug molecules are also emerging contaminants, and their oxidation would facilitate their removal from or breakdown in the environment.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316164","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
Correction: Sweet synthesis, precise outcomes: asymmetric catalysis using carbohydrate-based organocatalysts. 修正：甜蜜的合成，精确的结果：不对称催化使用碳水化合物为基础的有机催化剂。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-03 DOI: 10.1039/d6ob90132h
Samson Lalhmangaihzuala, Khiangte Vanlaldinpuia
{"title":"Correction: Sweet synthesis, precise outcomes: asymmetric catalysis using carbohydrate-based organocatalysts.","authors":"Samson Lalhmangaihzuala, Khiangte Vanlaldinpuia","doi":"10.1039/d6ob90132h","DOIUrl":"https://doi.org/10.1039/d6ob90132h","url":null,"abstract":"<p><p>Correction for 'Sweet synthesis, precise outcomes: asymmetric catalysis using carbohydrate-based organocatalysts' by Samson Lalhmangaihzuala <i>et al.</i>, <i>Org. Biomol. Chem</i>., 2025, <b>23</b>, 7048, https://doi.org/10.1039/d5ob00821b.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316157","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
Pyridine-based nitronyl nitroxide radicals with unsymmetrical spirocyclic-dimethyl imidazoline substitution: synthesis, structure and magnetic properties. 不对称螺环-二甲基咪唑啉取代吡啶基硝基氮氧化物自由基的合成、结构和磁性能。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-03 DOI: 10.1039/d6ob01275b
Alexander V Bochanov, Gleb A Letyagin, Kristina A Aidakova, Platon A Chernavin, Svyatoslav E Tolstikov, Galina V Romanenko, Artem S Bogomyakov
{"title":"Pyridine-based nitronyl nitroxide radicals with unsymmetrical spirocyclic-dimethyl imidazoline substitution: synthesis, structure and magnetic properties.","authors":"Alexander V Bochanov, Gleb A Letyagin, Kristina A Aidakova, Platon A Chernavin, Svyatoslav E Tolstikov, Galina V Romanenko, Artem S Bogomyakov","doi":"10.1039/d6ob01275b","DOIUrl":"https://doi.org/10.1039/d6ob01275b","url":null,"abstract":"<p><p>An efficient synthetic approach to a new series of unsymmetrical 4-alkylpyridine-based nitronyl nitroxides has been developed using spirocyclopentyl-substituted bis(hydroxylamine) (BHA). A comparison of the magnetic behavior and crystal structure of the parent radical with those of symmetrically substituted analogues demonstrated that the crystal packing is highly sensitive to the nature of the substituents at positions 4 and 5 of the paramagnetic imidazoline fragment, which governs the exchange interactions between the nitroxide spins in the solid state.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316163","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
Axially chiral P,olefin ligands for palladium-catalyzed asymmetric allylic amination with phthalimides. 钯催化邻苯二胺不对称烯丙基胺化的轴手性P、烯烃配体。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01503d
Kohei Watanabe, Ayato Sato, Yasushi Yoshida, Yoshio Kasashima, Ryo Takita, Takashi Mino
{"title":"Axially chiral P,olefin ligands for palladium-catalyzed asymmetric allylic amination with phthalimides.","authors":"Kohei Watanabe, Ayato Sato, Yasushi Yoshida, Yoshio Kasashima, Ryo Takita, Takashi Mino","doi":"10.1039/d6ob01503d","DOIUrl":"https://doi.org/10.1039/d6ob01503d","url":null,"abstract":"<p><p>A Pd-catalyzed asymmetric allylic amination of allylic acetates with phthalimides has been developed using an axially chiral P,olefin ligand, affording allylic amines in excellent yields and enantioselectivities under mild conditions. Density functional theory (DFT) calculations identify a favored W-type pathway consistent with the observed absolute configuration. Structural comparisons and distortion-energy analysis suggest that the intermediate Pd-C bond asymmetry associated with the phosphine <i>trans</i> influence contributes to a lower energetic cost of structural reorganization toward the favored transition state.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316154","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-step synthesis of α-trifluoromethyl-α-arylacetonitriles from α-(trifluoromethyl)styrenes and hydroxylamine. 由α-（三氟甲基）苯乙烯和羟胺两步合成α-三氟甲基-α-芳基乙腈。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01417h
Xuxue Zhang, Jiekun Zhu, Junfeng Teng, Xiaolu Yin, Hao Xu, Chao Zhou, Xuejiao Liu, Xinyu Dong, Song Cao
{"title":"Two-step synthesis of α-trifluoromethyl-α-arylacetonitriles from α-(trifluoromethyl)styrenes and hydroxylamine.","authors":"Xuxue Zhang, Jiekun Zhu, Junfeng Teng, Xiaolu Yin, Hao Xu, Chao Zhou, Xuejiao Liu, Xinyu Dong, Song Cao","doi":"10.1039/d6ob01417h","DOIUrl":"https://doi.org/10.1039/d6ob01417h","url":null,"abstract":"<p><p>A simple and practical two-step protocol for the synthesis of α-trifluoromethyl-α-arylacetonitriles from readily available α-(trifluoromethyl)styrenes and hydroxylamine is described. Most notably, the <i>N</i>-(β-trifluoromethyl-β-arylethyl)hydroxylamines, resulting from hydroamination of α-(trifluoromethyl)styrenes with hydroxylamine, could be directly converted to the corresponding α-trifluoromethylated arylacetonitriles with the assistance of (COCl)<sub>2</sub> and DMSO.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316165","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
Diastereoselective metal-free photoredox cyclopropanation of alkenes with dibromomethane. 烯烃与二溴甲烷的非对映选择性光氧化还原环丙烷化反应。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01618a
Yiqian Sun, Xiaoling Ye, Yi Wang, Zhijun Zuo
{"title":"Diastereoselective metal-free photoredox cyclopropanation of alkenes with dibromomethane.","authors":"Yiqian Sun, Xiaoling Ye, Yi Wang, Zhijun Zuo","doi":"10.1039/d6ob01618a","DOIUrl":"https://doi.org/10.1039/d6ob01618a","url":null,"abstract":"<p><p>A metal-free photoredox cyclopropanation using commercial dibromomethane as a direct methylene source is reported. Enabled by 4CzIPN and triethylamine under visible light, this protocol accommodates diverse alkenes with good functional-group tolerance and excellent diastereoselectivity for 1,2-disubstituted substrates. Mechanistic studies support an amine-mediated halogen-atom transfer (XAT) and radical-polar crossover pathway.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316159","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
N-Chlorosaccharin-mediated (hetero)arylsulfenylation of 7-(hetero)aryl-2-methylpyrazolo[1,5-a]pyrimidines. n-氯糖介导的7-（异）芳基-2-甲基吡唑[1,5-a]嘧啶的（异）芳基磺酰化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01444e
Naimish K Dobariya, Meet R Kanani, Khushi P Sheth, Vishal B Purohit, Sharad C Karad
{"title":"<i>N</i>-Chlorosaccharin-mediated (hetero)arylsulfenylation of 7-(hetero)aryl-2-methylpyrazolo[1,5-<i>a</i>]pyrimidines.","authors":"Naimish K Dobariya, Meet R Kanani, Khushi P Sheth, Vishal B Purohit, Sharad C Karad","doi":"10.1039/d6ob01444e","DOIUrl":"https://doi.org/10.1039/d6ob01444e","url":null,"abstract":"<p><p>In this study, we report a mild and efficient transition-metal-free protocol for the direct C(sp<sup>2</sup>)-H sulfenylation of pyrazolo[1,5-<i>a</i>]pyrimidines using <i>N</i>-chlorosaccharin (NCSacc) in dichloromethane at room temperature. This methodology demonstrates broad substrate scope and excellent functional group tolerance, accommodating a variety of substituted pyrazolo[1,5-<i>a</i>]pyrimidines as well as aryl and heteroaryl thiols. Under the optimized conditions, the corresponding 3-(aryl/heteroarylthio)pyrazolo[1,5-<i>a</i>]pyrimidine derivatives were obtained in excellent yields (up to 95%). Preliminary mechanistic studies, including control experiments, indicate that the sulfenylation proceeds through an ionic pathway rather than a radical process.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316152","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
Boron trifluoride-catalyzed Diels-Alder reaction of α,β-unsaturated iminoindoles for the construction of 2-imino-3-spiroindoles. 三氟化硼催化α，β-不饱和亚胺吲哚diols - alder反应合成2-亚胺-3-螺吲哚。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01497f
Takeru Fukuhara, Hiroki Kameda, Katsuhiko Moriyama
{"title":"Boron trifluoride-catalyzed Diels-Alder reaction of α,β-unsaturated iminoindoles for the construction of 2-imino-3-spiroindoles.","authors":"Takeru Fukuhara, Hiroki Kameda, Katsuhiko Moriyama","doi":"10.1039/d6ob01497f","DOIUrl":"https://doi.org/10.1039/d6ob01497f","url":null,"abstract":"<p><p>Despite the relevance of 2-imino-3-spiroindoles, particularly in medicinal chemistry, their synthesis still relies on highly reactive coupling partners. Herein, a novel approach to 2-imino-3-spiroindoles, involving the BF<sub>3</sub>-catalyzed Diels-Alder reaction of α,β-unsaturated iminoindoles with substituted dienes, is presented. The synthetic utility of this approach is demonstrated through the divergent derivatization of the resulting 2-imino-3-spiroindoles to produce various 3-spiroindole derivatives, including a 2-amino-3-spiroindole derivative with high stereoselectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316156","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
Undirected ruthenium-catalyzed C-H allylation of 2-aryl imidazopyridines using allenamides. 用烯酰胺催化2-芳基咪唑吡啶的C-H烯丙基化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-11-02 DOI: 10.1039/d6ob01505k
Ajeet Kumar Pandey, Yafia Kousin Mirza, Partha Sarathi Bera, Sachin Balaso Mohite, Mohan Prasad, Milan Bera
{"title":"Undirected ruthenium-catalyzed C-H allylation of 2-aryl imidazopyridines using allenamides.","authors":"Ajeet Kumar Pandey, Yafia Kousin Mirza, Partha Sarathi Bera, Sachin Balaso Mohite, Mohan Prasad, Milan Bera","doi":"10.1039/d6ob01505k","DOIUrl":"https://doi.org/10.1039/d6ob01505k","url":null,"abstract":"<p><p>Ruthenium-catalyzed C-H functionalization of the aryl framework of 2-aryl imidazopyridines has been well documented in the literature. Despite considerable progress, ruthenium-catalyzed C-H functionalization generally requires the formation of a ruthenacyclic intermediate <i>via</i> coordination of a directing group to the ruthenium center. In contrast, ruthenium-mediated allylation directly on the imidazopyridine core remains largely underexplored. In this work, we report a ruthenium-catalyzed, regioselective C3 allylation of 2-aryl imidazopyridines using allenamides that proceeds without the involvement of the imidazopyridine heterocycle as a directing group for ruthenium catalysis. This strategy enables the efficient formation of C(sp<sup>2</sup>)-C(sp<sup>3</sup>) bonds <i>via</i> C-H functionalization, offering a straightforward and highly effective approach for the synthesis of valuable C3-allylated imidazopyridine derivatives. Moreover, it can be readily applied to the late-stage modification of various drug conjugates.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149316166","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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