{"title":"Pyridinium‐Based Schiff‐Base Fluorescent Chemosensor for Sequential Detection of Al3+ Ions and TNP: Applications in Cell Imaging and Latent Fingerprint Visualization","authors":"Pragya , Sonali J. Jain , Krishnan Rangan , Prabhat Nath Jha , Bharti Khungar","doi":"10.1002/ajoc.202400669","DOIUrl":"10.1002/ajoc.202400669","url":null,"abstract":"<div><div>A fluorescent pyridinium‐based chemosensor (E)‐1‐(2‐(3‐hydroxy‐4‐((pyridin‐2‐ylimino) methyl) phenoxy) ethyl) pyridin‐1‐ium bromide (<strong>BzPySB</strong>) was synthesized and characterized using various spectroscopic techniques. The chemosensing potential of <strong>BzPySB</strong> was explored using UV‐vis and fluorescence spectroscopy in the aqueous medium. The turn‐on fluorescence behavior was observed for <strong>BzPySB</strong> in the presence of Al<sup>3+</sup>, while other metal ions were non‐responsive. The B−H and Job′s plot confirmed the 1 : 1 stoichiometric ratio of the <strong>BzPySB</strong> and Al<sup>3+</sup>. The in situ generated complex <strong>BzPySB</strong>‐Al<sup>3+</sup> offered selectivity toward TNP via fluorescence turn‐off phenomena with high <em>K</em><sub>sv</sub> and LOD values. The “off‐on‐off” sensing mechanism was elucidated through <sup>1</sup>H NMR, mass spectrometry, and DFT calculations. The probe also detected Al<sup>3+</sup> in plant and MCF‐7 cells, highlighting its potential in biological systems. Moreover, <strong>BzPySB</strong> exhibited solid‐state luminescent properties credited to weak <em>π‐π</em> interaction, leading to its successful application in the visualization of latent fingerprints.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400669"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622492","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Juan Tian , Shimin Yang , Ying Peng , Mengyun Chen , Xin Chen , Xinyi Wang , Dayong Sang
{"title":"Deacylation of N‐Acylsulfonamides Mediated by Metal Triflimides","authors":"Juan Tian , Shimin Yang , Ying Peng , Mengyun Chen , Xin Chen , Xinyi Wang , Dayong Sang","doi":"10.1002/ajoc.202400673","DOIUrl":"10.1002/ajoc.202400673","url":null,"abstract":"<div><div><em>N</em>‐Acylsulfonamides play a significant role in organic and medicinal chemistry. The <em>N</em>‐deacylation of <em>N</em>‐acylsulfonamides is an important transformation that releases the sulfonamide structural motif. Herein, a metal triflimide‐catalyzed nonhydrolytic method for the deacylation of <em>N</em>‐acylsulfonamides is presented. Commercially available metal triflimides reactive for the <em>N</em>‐deacylation include Cu(NTf<sub>2</sub>)<sub>2</sub>, Zn(NTf<sub>2</sub>)<sub>2</sub>, Mg(NTf<sub>2</sub>)<sub>2</sub>, Ce(NTf<sub>2</sub>)<sub>3</sub>, and La(NTf<sub>2</sub>)<sub>3</sub>. A range of <em>N</em>‐acyl groups, including acetyl, propionyl, butyryl, isobutyryl, octanoyl, benzoyl, 2‐phenylacetyl, and sterically hindered pivaloyl are readily deblocked efficiently. A variety of functional groups, such as halogeno, keto, nitro, cyano, ether, and carboxylate, are tolerated intact.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400673"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622288","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Leysan I. Gallyamova , Alfiya R. Bayguzina , Ilfir R. Ramazanov
{"title":"Synthesis of N‐,O‐,S‐Heterocyclic Spiroadamantanes by Condensation of Ketones with Bifunctional OH‐, NH‐, SH‐Acids under the Action of Copper‐Containing Catalysts","authors":"Leysan I. Gallyamova , Alfiya R. Bayguzina , Ilfir R. Ramazanov","doi":"10.1002/ajoc.202400276","DOIUrl":"10.1002/ajoc.202400276","url":null,"abstract":"<div><div>Synthesis of adamantyl‐containing cyclic ketals, spirooxazolidines, spiroimidazolidines, spirooxathiolanes, spirodithiolanes, spirooxazines, spirobenzodioxoles with high yields was carried out by condensation of adamantyl‐containing ketones (adamantanone, kemantan, diamantanone) with diols, 1,2‐ethanedithiol and 2‐mercaptoethanol, 1,2‐diaminoethane and 2‐aminoethanol under the action of copper‐containing catalysts. In the case of multigram‐scale reaction of adamant‐2‐one with 1,2‐propanediol, the amount of catalyst can be reduced to 0.1 mol %.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400276"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622345","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Prof. Dr. Tsuyoshi Murata , Satsuki Doi , Rina Ishikawa , Prof. Dr. Ko Furukawa , Prof. Dr. Yasushi Morita
{"title":"π‐Expansion on a Polycyclic Stable Neutral Radical: Synthesis and Physical Properties of a Benz‐Annulated Trioxotriangulene","authors":"Prof. Dr. Tsuyoshi Murata , Satsuki Doi , Rina Ishikawa , Prof. Dr. Ko Furukawa , Prof. Dr. Yasushi Morita","doi":"10.1002/ajoc.202400690","DOIUrl":"10.1002/ajoc.202400690","url":null,"abstract":"<div><div>We report the synthesis of a benz‐annulated derivative of trioxotriangulene (<strong>TOT</strong>), a fused polycyclic organic neutral radical, and also the investigation on the electronic effects of π‐expansion. The neutral radical species was highly stable under air in both solution and solid states. Quantum chemical calculation suggested that the molecule has a completely planar molecular structure, and the electronic spin is widely delocalized throughout the π‐skeleton while maintaining three‐fold symmetry, which was experimentally supported by electronic spin resonance spectrum. The neutral radical also showed a strong π‐association ability comparable to that of <strong>TOT</strong> neutral radical derivatives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400690"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622610","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Photocatalytic Deoxygenative Alkylation with Alcohols via Xanthates or Thionocarbonates","authors":"Wei Luo , Zhong Chen , Prof. Dr. Bing Yu","doi":"10.1002/ajoc.202400627","DOIUrl":"10.1002/ajoc.202400627","url":null,"abstract":"<div><div>Recent advancements in photocatalytic strategies have expanded the range of alkylating agents, including alkyl carboxylic acids and saturated hydrocarbons. Notably, alcohols are preferred for their availability, stability, and safety compared to traditional alkylating reagents such as alkyl halides. This review summarizes recent developments in photocatalytic deoxygenative alkylation using alcohols, specifically through the formation of xanthates or thionocarbonates.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400627"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Enantioselective Synthesis of 2‐Substituted 2‐Hydroxymethylaziridines by Copper‐Catalyzed Sulfonylative Desymmetrization of 2‐Amino‐1,3‐Diols","authors":"Kosuke Yamamoto , Eibu Sakata , Anri Uehara , Masami Kuriyama , Osamu Onomura","doi":"10.1002/ajoc.202400643","DOIUrl":"10.1002/ajoc.202400643","url":null,"abstract":"<div><div>An enantioselective protocol for the synthesis of 2‐hydroxymethylaziridines with a tetrasubstituted carbon stereocenter have been established through the copper‐catalyzed asymmetric desymmetrization of 2‐substituted 2‐amino‐1,3‐diol derivatives by monosulfonylation. The present transformation consists of a reaction sequence involving the enantioselective monosulfonylation of 2‐amino‐1,3‐diols and the intramolecular ring closure of the resultant monosulfonylated products, which provides an efficient and straightforward entry to optically active 2‐substituted 2‐hydroxymethylaziridines. The potential synthetic utility of the present reaction is exemplified by the derivatization of the obtained aziridines into a variety of nitrogen‐containing molecules such as amino alcohols and functionalized aziridine derivatives with high enantiopurities.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400643"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yuito Takatsuji , Prof. Dr. Yoshinosuke Usuki , Prof. Dr. Tetsuya Satoh
{"title":"Rhodium(III)‐Catalyzed Arylation of Dimethyl Itaconate: Facile Access to Substituted Benzylidenesuccinates","authors":"Yuito Takatsuji , Prof. Dr. Yoshinosuke Usuki , Prof. Dr. Tetsuya Satoh","doi":"10.1002/ajoc.202400589","DOIUrl":"10.1002/ajoc.202400589","url":null,"abstract":"<div><div>The rhodium(III)‐catalyzed arylation of dimethyl itaconate with arylboronic acids proceeds smoothly under mild conditions to produce benzylidenesuccinates. The present reaction provides a simple synthesis route to benzylidenesuccinates, which are of interest due to their biological activities, from readily available substrates.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400589"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622340","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Nikhil Sodhi , Manish Kumar , Manisha Yadav , Rajni Kadian , Sena Atici , Dr. Jose Pedro Friedmann Angeli , Dr. Vijay P. Singh
{"title":"Glutathione Peroxidase‐Mimics Organoselenium Amines: Anti‐Ferroptotic Properties and an In Silico Study of 15‐Lipoxygenase‐2","authors":"Nikhil Sodhi , Manish Kumar , Manisha Yadav , Rajni Kadian , Sena Atici , Dr. Jose Pedro Friedmann Angeli , Dr. Vijay P. Singh","doi":"10.1002/ajoc.202400606","DOIUrl":"10.1002/ajoc.202400606","url":null,"abstract":"<div><div>In search for better synthetic antioxidants, aminic organoselenides carrying amine and benzamide groups at <em>ortho</em>‐positions to the selenium atom were synthesized from alkyl halides and <em>in situ</em> generated sodiumselenolates as nucleophile by the sodium borohydride reduction of corresponding diselenides. The single crystal X‐ray structure of one compound showed the weak intramolecular Se⋅⋅⋅H interactions with free amine group. The presence of Se⋅⋅⋅H interactions was further confirmed using natural bond orbital (NBO) and atoms in molecules (AIM) calculations, respectively. The glutathione peroxidase enzyme (GPx)‐like antioxidant activity of all compounds was evaluated using thiophenol assay. The best antioxidant exhibited nearly 5 and 10 times greater activities than Oct<sub>2</sub>Se<sub>2</sub> and Ph<sub>2</sub>Se<sub>2</sub> used as references, respectively. The most active catalysts carrying a strong electron‐donating group were further investigated at different concentrations of thiol for determining the catalytic parameters. These GPx mimics have shown anti‐ferroptotic activity in a 4‐OH‐tamoxifen (TAM) inducible GPx4 knockout cell line and protected cells from cell death induced by loss of GPx4 enzyme. <em>In silico</em> molecular docking studies showed that all antioxidants demonstrated promising Moldock scores with human 15‐lipoxygenase‐2 enzyme.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400606"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622344","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dr. Kuan‐Hsun Huang , Yao‐Ping Lo , Dr. Anupam Mukherjee , Dr. Badugu Devendar , Sandeep Sharma , I.‐Chen Chiu , Yu‐Pei Chang , Yi‐Chuan Chang , Prof. Chi‐Phi Wu , Prof. Chun‐Chen Liao , Prof. Gary Jing Chuang
{"title":"A Practical Approach to Cyclopropanation of Masked o‐Benzoquinones with Applications in Tropolone Derivative Synthesis","authors":"Dr. Kuan‐Hsun Huang , Yao‐Ping Lo , Dr. Anupam Mukherjee , Dr. Badugu Devendar , Sandeep Sharma , I.‐Chen Chiu , Yu‐Pei Chang , Yi‐Chuan Chang , Prof. Chi‐Phi Wu , Prof. Chun‐Chen Liao , Prof. Gary Jing Chuang","doi":"10.1002/ajoc.202400659","DOIUrl":"10.1002/ajoc.202400659","url":null,"abstract":"<div><div>The Corey–Chaykovsky cyclopropanation of readily available masked <em>o</em>‐benzoquinones (MOBs) has been investigated to generate functionalized bicyclo[4.1.0]heptane derivatives with regioselectivity. The resulting bicyclic products were subjected to a sequence of hydrolysis, BF₃ ⋅ Et₂O‐mediated ring‐opening, and then again hydrolysis to access various tropolone derivatives – a class of molecules with significant roles in synthetic, biological, and theoretical chemistry. Utilizing an improved approach based on established cyclopropanation and ring‐opening strategies, several bicyclo[4.1.0]heptanes, tropolone difluorides, and tropolones can be synthesized from readily available MOBs. Our efforts focused on modifying each step to make these reactions general and of considerable practical value.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400659"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622346","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cuili Chen , Shan Lu , Yanmin Zou , Di Mao , Hideaki Kakeya
{"title":"Secondary Metabolites from Tripterygium wilfordii Hook. f.‐Associated Endophytes: Producing Microbes, Structures, and Bioactivities","authors":"Cuili Chen , Shan Lu , Yanmin Zou , Di Mao , Hideaki Kakeya","doi":"10.1002/ajoc.202400696","DOIUrl":"10.1002/ajoc.202400696","url":null,"abstract":"<div><div>Endophytes have been recognized as important sources for discovering novel bioactive natural products with diverse structures and biological activities. This review focuses on the endophytes of <em>Tripterygium wilfordii</em> Hook. f. (<em>T. wilfordii</em>), a famous traditional medicinal plant, and summarizes the producing microbes, chemical diversities, and bioactivities of the metabolites discovered from the <em>T. wilfordii</em> ‐associated endophytes over the past thirty years (1995–2024). One hundred and one metabolites together with their bioactivities from twelve endophytes are systematically reviewed. A comprehensive comparison of the 101 metabolites with those isolated from <em>T. wilfordii</em> reveals that the <em>T. wilfordii</em>‐associated endophytes produce structurally distinct metabolites with diverse biological activities. To the best of our knowledge, this is the first holistic overview of the <em>T. wilfordii</em>‐associated endophytes and their secondary metabolites.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400696"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}