Asian Journal of Organic Chemistry最新文献

{"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,&nbsp;Saloni Mishra,&nbsp;Anuj S. Sharma,&nbsp;Neha Sharma,&nbsp;Rajender S. Varma,&nbsp;Pranav S. Shrivastav,&nbsp;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,&nbsp;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":"Ultrasmall Fe3O4 Nanoparticles on ZrO2 as Catalysts for CO2 Hydrogenation to Lower Olefins","authors":"Huda S. Alghamdi ,&nbsp;Mohammed A. Sanhoob ,&nbsp;Afnan M. Ajeebi ,&nbsp;Md. Abdul Aziz ,&nbsp;M. Nasiruzzaman Shaikh ,&nbsp;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 (CO₂) in the atmosphere into a more sustainable carbon source. To reduce the carbon footprint, we explored the direct hydrogenation of CO₂ to lower (C_2‐4⁼) olefins using various catalysts composed of ZrO₂‐supported alkali‐metal‐promoted superparamagnetic iron oxide nanoparticles (SPIONs; Fe₃O₄). 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 ZrO₂. Results showed that the strong interactions between Fe₃O₄ and the ZrO₂ support enhanced CO₂ hydrogenation performance compared to other forms.. Under optimal conditions – using a gas hourly space velocity (GHSV) of 4500 mL/h/g_cat. and a feed ratio of H₂:CO₂=3 : 1 – this catalyst achieved over 22 % CO₂ conversion and high selectivity for light (C_2–4⁼) olefins at 30 bar and 375 °C, with 30 wt% Fe₃O₄ loading on ZrO₂ 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}

{"title":"Facile Synthesis of 1,4,2‐Dioxazines Using Aromatic Chlorooximes and 2‐Chloroethanol/2‐Chlorophenols","authors":"Lavina Gladis Serrao ,&nbsp;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}

{"title":"Design and Synthesis of Novel Spiro [Chromane‐2,4′‐Piperidin]‐4‐One Derivatives: Anti‐Proliferative Investigation and Molecular Docking Studies","authors":"Srinuvasu Nakka ,&nbsp;Suryansh Sengar ,&nbsp;Kosana Sai Chaitanya ,&nbsp;Swati ,&nbsp;Ala Chandu ,&nbsp;Murugesan Sankaranarayanan ,&nbsp;Vivek Sharma ,&nbsp;Nagaraju Devunuri ,&nbsp;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 ¹H NMR, ¹³C 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 IC₅₀ values ranging 3.9–10 μM; against the cell line MCF‐7. The best compounds of all were <strong>KMS9</strong> (IC₅₀=3.83 μM), <strong>KMS5</strong> (IC₅₀=4.14 μM), and <strong>KBS8</strong> (IC₅₀=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 ,&nbsp;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}

{"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 ,&nbsp;Aswathi Ravindran N. E. ,&nbsp;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":"Mechanosynthesis of Enaminones and Mechanochemical Telescopic Synthesis of β,γ‐unsaturated Butyrolactams","authors":"Edson Evangelista ,&nbsp;Silvio Cunha","doi":"10.1002/ajoc.202400434","DOIUrl":"10.1002/ajoc.202400434","url":null,"abstract":"<div><div>The stereoselective mechanochemical synthesis of Z‐enaminones and bis‐enaminones was achieved without any solid component in most cases, reacting 1,3‐dicarbonyl compounds with aliphatic/aromatic primary/secondary amines, which demonstrates the viability of reacting exclusively liquid reagents. The scale‐up was robust, from five to fifty and five hundred mmol without reduction in the reaction yield. The mechanochemical telescopic synthesis of β,γ‐unsaturated butyrolactams was achieved by formal [3+2] azaanulation reaction of intermediate enaminone with maleic anhydride, boosting the access of this potentially bioactive class of compound. The mechanochemical approach revealed its sustainable face in both syntheses, avoiding solid grinding auxiliary and purification by column chromatography. A symbol was suggested to differentiate the representation of the planetary ball mill from other mechanochemical reactors, wherein three spheres are surrounded by two curved arrows representing the two inherent movements of planetary trajectories of the reaction vessel of this equipment.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400434"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424063","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 ,&nbsp;Rana Chatterjee ,&nbsp;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}

{"title":"Novel Cyclopropyl Appended 1,3‐Thiazole‐2‐Imines as Multi‐Target Agents: Design, Synthesis, Biological Evaluation and Computational Studies","authors":"Hina Zaman ,&nbsp;Aamer Saeed ,&nbsp;Tamknat ul Muntaha ,&nbsp;Hammad Ismail ,&nbsp;Muhammad Rashid","doi":"10.1002/ajoc.202400598","DOIUrl":"10.1002/ajoc.202400598","url":null,"abstract":"<div><div>In drug development, the 1,3‐thiazole‐2‐imines scaffolds are widely used to discern novel and potential therapies for the elimination of the most challenging diseases. The cyclopropyl motif is found in various medications such as antiviral drug Paxlovid, used to treat COVID‐19. Its presence enhances the metabolic stability and lipophilicity of drugs, making them more effective. Therefore, in the present work, we developed a library of novel cyclopropyl clubbed 1,3‐thiazole‐2‐imines (<strong>6 a</strong>–<strong>h</strong>) from the efficient cyclization between multistep synthesized thiourea precursors and ethyl 2‐chloroacetoacetate. Subsequently, the <em>in vitro</em> biological screening including antibacterial, <em>α</em>‐amylase, and proteinase K inhibition was carried out to assess their inhibition potential. In general, all synthesized compounds revealed moderate to significant potency. The compound (<strong>6 a</strong>) with no substitution at the phenyl ring exhibited the highest inhibitory activity amongst all, with an IC₅₀ value of 1.716±0.062 μM against proteinase K. Fortunately, this compound (<strong>6 a</strong>) also unfolded the most significant antibacterial potential against <em>B. subtilis</em> showing 20 mm zone of inhibition. The compound (<strong>6 d</strong>) possessing a naphthyl ring was found to be the most potent inhibitor of amylase displaying IC₅₀ value of 1.634±0.002 μM. Diverse substitution patterns on the framework of 1,3‐thiazole‐2‐imine pharmacophores provided a valuable basis for SAR analysis. Over and above, computational studies including DFT, molecular electrostatic potential, molecular docking, and ADMET were conducted to predict the chemical reactivity, ligand‐protein binding interactions, and drug‐likeness of synthesized compounds. Hence these studies highlighted our synthesized compounds as novel antibacterial, <em>α</em>‐amylase, and proteinase K inhibitors. Further research could be encouraged by modifying the substituents and their positions on the structure to attain the potent efficacy of these compounds.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":"Article e202400598"},"PeriodicalIF":2.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424238","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}