Prof. Dr. Takanori Suzuki , Dr. Wataru Nojo , Yuiki Kawada , Soichiro Sugiyama , Takaya Ikeuchi , Prof. Dr. Yusuke Ishigaki , Prof. Dr. Hiroaki Ohno
{"title":"Gold(I)‐catalyzed Synthesis of Axially Chiral Indolo[2,3‐c]carbazole Exhibiting Advanced Electrochromic Response","authors":"Prof. Dr. Takanori Suzuki , Dr. Wataru Nojo , Yuiki Kawada , Soichiro Sugiyama , Takaya Ikeuchi , Prof. Dr. Yusuke Ishigaki , Prof. Dr. Hiroaki Ohno","doi":"10.1002/ajoc.202400695","DOIUrl":"10.1002/ajoc.202400695","url":null,"abstract":"<div><div>The Wurster's Blue skeleton embedded in an axially chiral indolo[2,3‐<em>c</em>]carbazole framework can act as a key chromophore to realize three‐way‐output electrochromic response (UV‐Vis‐near IR absorption, fluorescence, and circular dichroism) upon reversible electrochemical interconversion with the corresponding neutral electron donor, which was effectively synthesized by gold(I)‐catalyzed cascade cyclization of 2‐azidophenyl‐1,3‐butadiyne with a 2‐phenyl‐1‐naphthyl terminal group.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400695"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622365","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}
Mónica G. Flores‐Amaro , María C. García‐López , David A. Velázquez Hernández , Horacio Reyes‐Pérez , Valeria Villarreal‐García , Rosa Martha Jiménez‐Barrera , Rodrigo Chan‐Navarro , Vianey González‐Villasana , Diana Reséndez‐Pérez.
{"title":"Blue‐LED Self‐Assembly‐Assisted Synthesis of New Photostable Organoboron Esters for Live‐Cell Imaging","authors":"Mónica G. Flores‐Amaro , María C. García‐López , David A. Velázquez Hernández , Horacio Reyes‐Pérez , Valeria Villarreal‐García , Rosa Martha Jiménez‐Barrera , Rodrigo Chan‐Navarro , Vianey González‐Villasana , Diana Reséndez‐Pérez.","doi":"10.1002/ajoc.202400613","DOIUrl":"10.1002/ajoc.202400613","url":null,"abstract":"<div><div>In this work, we report a blue‐LED self‐assembly‐assisted synthesis of novel emissive organoboron esters, achieved in just 30 minutes with quantitative yields. The molecular structure in solution (characterized by <sup>1</sup>H and <sup>11</sup>B NMR, and mass spectrometry) was further confirmed via X‐ray molecular diffraction analysis for compound <strong>3</strong>, where the boron ion adopts a distorted tetrahedral geometry. The photophysical properties of these molecules were analyzed in solution, revealing that <strong>1</strong>, featuring <em>tert</em>‐butyl groups and boron heterocycles with a nitro‐substituent, exhibits superior photostability compared to its derivatives. Photobleaching values showed an inverse correlation with the oxidation potentials of compounds <strong>1</strong>–<strong>3</strong>, except for <strong>4</strong>, used as a reference. Mass spectrometry further revealed greater energetic stability of the molecular ion of <strong>1</strong>. Notably, compound <strong>3</strong> demonstrated good solubility, high photostability, and adequate biocompatibility, making it a promising fluorescent dye for biomedical applications. Cytotoxicity assays in HEK‐293 cells across different concentrations confirmed its non‐toxic nature. Theoretical calculations further supported the high chemical stability of all compounds, attributing it to a synergistic interaction between electronic and steric effects, which protect the fluorophores by substitution of Schiff bases and formation of boron heterocycles. Additionally, <strong>3</strong> exhibited strong, non‐hazardous blue fluorescence when tested on HEK‐293 and MDA‐MB‐231 cells.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400613"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622660","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}
Vinay S. Sharma, Saloni Mishra, Anuj S. Sharma, Neha Sharma, Rajender S. Varma, Pranav S. Shrivastav, Achalkumar Ammathnadu Sudhakar
{"title":"Cover Feature: Microcrystalline Cellulose and Cellulose Nanocrystals: Ecofriendly and Sustainable Support Materials in Heterogeneous Nanocatalysis for Green Organic Transformations (Asian J. Org. Chem. 2/2025)","authors":"Vinay S. Sharma, Saloni Mishra, Anuj S. Sharma, Neha Sharma, Rajender S. Varma, Pranav S. Shrivastav, Achalkumar Ammathnadu Sudhakar","doi":"10.1002/ajoc.202580202","DOIUrl":"https://doi.org/10.1002/ajoc.202580202","url":null,"abstract":"<p>The cover design illustrates the applicability of microcrystalline cellulose and cellulose nanocrystals in organic transformations. In the illustration, an organic chemist is excited to explore the wide potential of these commercially viable materials in various sustainable organic reactions within the green forest of cellulose. Microcrystalline cellulose and cellulose nanocrystals offer high catalytic efficiency and selectivity in organic reactions, promoting greener and more sustainable processes. The biocompatibility and renewable nature of these materials attract the attention of organic chemists, especially when compared to traditional catalysts. More details can be found inarticle number e202400586 by Pranav S. Shrivastav, Achalkumar Ammathnadu Sudhakar, and co-workers.<figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202580202","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423950","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Front Cover: Biosynthesis of Depsides, Depsidones, and Diphenyl Ethers from Fungi and Lichens (Asian J. Org. Chem. 2/2025)","authors":"Qiaolin Ji, Dr. Yudai Matsuda","doi":"10.1002/ajoc.202580201","DOIUrl":"https://doi.org/10.1002/ajoc.202580201","url":null,"abstract":"<p>This review article summarizes the recent advances in the biosynthetic studies on depsides, depsidones, and diphenyl ethers from fungi and lichens. The mechanisms behind their backbone synthesis and structural diversification are discussed. This cover picture illustrates that non-reducing polyketide synthases (NR-PKSs) are the central enzymes for their biosynthesis. More details can be found inarticle number e202400451 by Qiaolin Ji and Yudai Matsuda.<figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202580201","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424036","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Design and Synthesis of Novel Spiro [Chromane‐2,4′‐Piperidin]‐4‐One Derivatives: Anti‐Proliferative Investigation and Molecular Docking Studies","authors":"Srinuvasu Nakka , Suryansh Sengar , Kosana Sai Chaitanya , Swati , Ala Chandu , Murugesan Sankaranarayanan , Vivek Sharma , Nagaraju Devunuri , Kondapalli Venkata Gowri Chandra Sekhar","doi":"10.1002/ajoc.202400604","DOIUrl":"10.1002/ajoc.202400604","url":null,"abstract":"<div><div>Chemists around the globe are extensively working for remedial solutions to cancer, one of the greatest health hazards. We have synthesized twenty‐three novel spiro [chromane‐2,4′‐piperidin]‐ 4 ‐one derivatives (<strong>KBS</strong> and <strong>KMS</strong> series of analogues) as part of our ongoing research to combat this deadly disease, and confirmed their structures using <sup>1</sup>H NMR, <sup>13</sup>C NMR, HRMS, and FT‐IR. Furthermore, we employed single‐crystal XRD to identify the compound structures of <strong>KBS4</strong> and <strong>KMS10</strong>. We have tested the compounds on the cell line such as MCF‐7; U87‐MG; SCC‐25; and HEK‐293T, via WST‐1 assay. Eight compounds showed IC<sub>50</sub> values ranging 3.9–10 μM; against the cell line MCF‐7. The best compounds of all were <strong>KMS9</strong> (IC<sub>50</sub>=3.83 μM), <strong>KMS5</strong> (IC<sub>50</sub>=4.14 μM), and <strong>KBS8</strong> (IC<sub>50</sub>=8.24 μM), which promoted apoptosis in MCF‐7 cells. <strong>KMS5</strong> and <strong>KMS9</strong> compounds showed G1 cell cycle arrest, while compound <strong>KBS8</strong> showed G2 cell cycle arrest. Insilco ADME studies were carried out. Molecular docking and dynamics experiments showed how <strong>KMS5</strong>, <strong>KMS9</strong>, and <strong>KBS8</strong> bind to the active region of the <strong>EGFR</strong> family – a group of receptor tyrosine kinase (RTK) proteins <strong>(PDB ID: 7JXP, 2.16 Å)</strong>. Further structural modifications of the <strong>KMS5, KMS9</strong>, and <strong>KBS8</strong> may improve their activity against breast cancer.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400604"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424239","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":"Biosynthesis of Depsides, Depsidones, and Diphenyl Ethers from Fungi and Lichens","authors":"Qiaolin Ji , Dr. Yudai Matsuda","doi":"10.1002/ajoc.202400451","DOIUrl":"10.1002/ajoc.202400451","url":null,"abstract":"<div><div>Depsides are a class of natural products in which two or more (poly)phenolic acid derivatives are linked by an ester bond. Depsides and related natural products, such as depsidones and diphenyl ethers, are widespread in nature and exhibit a wide range of biological activities. Although their biosynthesis has attracted considerable research interest for many decades, it remained largely elusive until recently. Recent studies have revealed the molecular mechanisms underlying the biosynthesis of several depsides and related natural products, uncovering unique enzymatic chemistry in their biosynthetic pathways. This review summarizes the biosynthetic pathways and mechanisms for depsides, depsidones, and diphenyl ethers, focusing on fungi and lichens, which are the primary producers of these compounds.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400451"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400451","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424297","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lavina Gladis Serrao , Dr. Mahagundappa Rachappa Maddani
{"title":"Facile Synthesis of 1,4,2‐Dioxazines Using Aromatic Chlorooximes and 2‐Chloroethanol/2‐Chlorophenols","authors":"Lavina Gladis Serrao , Dr. Mahagundappa Rachappa Maddani","doi":"10.1002/ajoc.202400475","DOIUrl":"10.1002/ajoc.202400475","url":null,"abstract":"<div><div>A facile and mild strategy for the synthesis of 5,6‐dihydro‐1,4,2‐dioxazines by the reaction of aromatic chlorooximes with 2‐chloroethanol in presence of NaH at room temperature in a short period of time is developed. This strategy is further extended for the synthesis of substituted 1,4,2‐dioxazines using aromatic chlorooximes and 2‐chlorophenols. Similarly, 5,6‐dihydro‐1,4,2‐dioxazepine was also synthesized using aromatic chlorooxime and 3‐bromopropanol. The developed protocol is simple, efficient and produces environmentally benign byproducts.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400475"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424064","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}
Huda S. Alghamdi , Mohammed A. Sanhoob , Afnan M. Ajeebi , Md. Abdul Aziz , M. Nasiruzzaman Shaikh , Lee Hwei Voon
{"title":"Ultrasmall Fe3O4 Nanoparticles on ZrO2 as Catalysts for CO2 Hydrogenation to Lower Olefins","authors":"Huda S. Alghamdi , Mohammed A. Sanhoob , Afnan M. Ajeebi , Md. Abdul Aziz , M. Nasiruzzaman Shaikh , Lee Hwei Voon","doi":"10.1002/ajoc.202400379","DOIUrl":"10.1002/ajoc.202400379","url":null,"abstract":"<div><div>Organic synthesis presents significant opportunities for converting the abundant and hazardous carbon dioxide (CO<sub>2</sub>) in the atmosphere into a more sustainable carbon source. To reduce the carbon footprint, we explored the direct hydrogenation of CO<sub>2</sub> to lower (C<sub>2‐4</sub><sup>=</sup>) olefins using various catalysts composed of ZrO<sub>2</sub>‐supported alkali‐metal‐promoted superparamagnetic iron oxide nanoparticles (SPIONs; Fe<sub>3</sub>O<sub>4</sub>). These catalysts are notable for their straightforward preparation; we employed a cost‐effective dry‐mixing method to create a range of alkali metal‐doped SPIONs supported on ZrO<sub>2</sub>. Results showed that the strong interactions between Fe<sub>3</sub>O<sub>4</sub> and the ZrO<sub>2</sub> support enhanced CO<sub>2</sub> hydrogenation performance compared to other forms.. Under optimal conditions – using a gas hourly space velocity (GHSV) of 4500 mL/h/g<sub>cat.</sub> and a feed ratio of H<sub>2</sub>:CO<sub>2</sub>=3 : 1 – this catalyst achieved over 22 % CO<sub>2</sub> conversion and high selectivity for light (C<sub>2–4</sub><sup>=</sup>) olefins at 30 bar and 375 °C, with 30 wt% Fe<sub>3</sub>O<sub>4</sub> loading on ZrO<sub>2</sub> and 2 wt% K promoter. We also investigated several variables, including alkali metal concentration, iron content, reaction conditions, and catalyst stability over 96 hours.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400379"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423702","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}
Rajasekharan Jayakumari Deepak , Aswathi Ravindran N. E. , Ramasamy Karvembu
{"title":"Solvent Dependent Selectivity in the Synthesis of 1,2‐Disubstituted and 2‐Substituted Benzimidazoles by Dehydrogenative Coupling Reactions with Ruthenium‐Polyoxoniobate Catalysts","authors":"Rajasekharan Jayakumari Deepak , Aswathi Ravindran N. E. , Ramasamy Karvembu","doi":"10.1002/ajoc.202400575","DOIUrl":"10.1002/ajoc.202400575","url":null,"abstract":"<div><div>Ruthenium‐polyoxoniobate complexes were found to be efficient catalysts for the selective synthesis of 2‐substituted benzimidazoles and 1,2‐disubstituted benzimidazoles by solvent switching. The current strategy enables the synthesis of 2‐substituted benzimidazoles in water as a green solvent. Switching to aprotic solvents resulted in the formation of 1,2‐disubstituted benzimidazoles as the major product. Control experiments showed the involvement of both acceptorless dehydrogenative and oxidative coupling pathways. The method was extended to synthesize various 2‐substituted and 1,2‐disubstituted benzimidazole derivatives, and the desired products were obtained in moderate to good yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400575"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423659","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":"Zinc‐Catalysed (3+2) Cycloaddition of Enaminone with Tosylhydrazide to Synthesise 1H‐Pyrazole via C−N and S−N Bond Cleavage","authors":"Sanjukta Roy , Rana Chatterjee , Rambabu Dandela","doi":"10.1002/ajoc.202400549","DOIUrl":"10.1002/ajoc.202400549","url":null,"abstract":"<div><div>A novel and practical zinc‐catalysed synthesis of 1<em>H</em>‐pyrazole has been developed. The one‐pot protocol enables the cycloaddition of enaminone and tosylhydrazide via C−N and S−N bond breaking process, leading to diverse mono‐substituted pyrazole derivatives in high yields. Moreover, the easily accessible materials, broad substrate scope with excellent functional group tolerance, ease of isolation and open‐air conditions are the key features of the present method.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400549"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423880","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}