Wenjun Liu , Xinghui Jin , Fang Yuan , Yuexia Wang , Jianhua Zhou , Qiong Wu
{"title":"A Promising Strategy for Searching High Energy Density Materials Based on 2,4,5‐Trinitro‐Imidazole Functional Backbone","authors":"Wenjun Liu , Xinghui Jin , Fang Yuan , Yuexia Wang , Jianhua Zhou , Qiong Wu","doi":"10.1002/ajoc.202400719","DOIUrl":"10.1002/ajoc.202400719","url":null,"abstract":"<div><div>A series of high energy density compounds are designed by altering the triazole, tetrazine, oxadiazole rings and energetic groups (such as −CN, −N<sub>3</sub>, −NH<sub>2</sub>, −NHNH<sub>2</sub>, −NO<sub>2</sub>, −NHNO<sub>2</sub>, −C(NO<sub>2</sub>)<sub>3</sub>, −CH(NO<sub>2</sub>)<sub>2</sub>) into 2,4,5‐trinitro‐imidazole skeleton. Their structures are optimized by density functional theory (DFT) methods at B3LYP/6‐311G (d,p) method. Based on the optimized structures, the impact of different rings and energetic groups on their energy gaps, heats of formation, detonation performance and sensitivities are investigated. The results show that compound F4 possesses the highest values of heats of formation due to their high nitrogen content. However, compound F2 possesses the highest values of detonation pressure and detonation velocity which indicates that the detonation performance are determined by values of density rather than those of heats of formation. Taking both detonation performance and impact sensitivities into consideration, compounds B4, C4, F4, I4, J4 and J8 are screened as high energy density compounds due to their excellent detonation performance and acceptable sensitivities compared to those of RDX. Finally, the distribution of frontier molecular orbital, the electrostatic potential area distribution, thermodynamic properties and weak interactions of the screened compounds are fully investigated.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400719"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622281","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}
Liang Ye , Haibin Xu , Jiong Yu , Han Yan , Min Wang , Pinhua Li
{"title":"Photocatalytic Cascade Alkylation/Cyclization of N‐Arylacrylamides with Simple Alkanes: A Convenient Approach to Quaternary C3 Alkylated Oxindoles","authors":"Liang Ye , Haibin Xu , Jiong Yu , Han Yan , Min Wang , Pinhua Li","doi":"10.1002/ajoc.202400554","DOIUrl":"10.1002/ajoc.202400554","url":null,"abstract":"<div><div>A convenient and efficient protocol for the synthesis of 3,3‐dialkylated oxindoles through photocatalytic aerobic radical‐cascade alkylation/cyclization of <em>N</em>‐arylacrylamides with the alkyl radicals generated from simple alkanes is described. This method features a broad substrate scope, inexpensive alkyl radical precursors, simple conditions and good yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400554"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622550","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}
Yulong Zhang , Hang Wang , Bin Gu , Bowen Hu , Dr. Xiaoxue Tang , Prof. Dr. Yushuang Chen
{"title":"FeCl3‐Promoted Conjugate Reduction of Exocyclic α,β‐Unsaturated Ketones with Polymethylhydrosiloxane","authors":"Yulong Zhang , Hang Wang , Bin Gu , Bowen Hu , Dr. Xiaoxue Tang , Prof. Dr. Yushuang Chen","doi":"10.1002/ajoc.202400691","DOIUrl":"10.1002/ajoc.202400691","url":null,"abstract":"<div><div>A new iron catalytic conjugate reduction of exocyclic α,β‐unsaturated carbonyl compounds with PMHS has been established for the first time. The reaction utilized PMHS as readily available, non‐toxic, and mild reductant that can be handled in open air. This protocol exhibits high compatibility with various substituents, and gives excellent yields, providing an environmentally benign and efficient access to construct synthetically useful α‐benzyl cyclic ketone scaffolds.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400691"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622447","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":"ortho‐Selective Suzuki Coupling of Dichlorophenol and Dichlorobenzylalcohol in Water under Palladium Catalysis Directed by Noncovalent Interactions and Computational Analysis","authors":"Shangxun Zhao , Shuo Wen , Hongrun Chen , Kewei Zhan , Jiawei Weng , Danli Ding , Xingwei Cai , Heng Song , Chen Xu","doi":"10.1002/ajoc.202400581","DOIUrl":"10.1002/ajoc.202400581","url":null,"abstract":"<div><div>The use of attractive noncovalent interactions is emerging as a versatile approach to address site‐selectivity challenges. Herein, we report ortho‐selective Suzuki coupling reactions in water of 2,3‐dichloroarenes and 2,4‐dichloroarenes bearing a hydroxy group in the presence of a palladacycle catalyst and directed by noncovalent interactions. Various ortho‐substituted arylphenols and arylbenzyl alcohols were obtained in good to excellent yields with high selectivity. Density functional theory (DFT) calculations and ab initio molecular dynamics (AIMD) simulations suggested that the <em>ortho</em>‐selective Suzuki coupling of dichlorophenols and dichlorobenzyl alcohols occurred through electrostatic interactions and hydrogen bonding interactions, respectively.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400581"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622430","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":"Hydrostability of Boroxines","authors":"Dr. Kosuke Ono","doi":"10.1002/ajoc.202400683","DOIUrl":"10.1002/ajoc.202400683","url":null,"abstract":"<div><div>Boroxines, six‐membered heterocyclic compounds with alternating O and B atoms, are readily formed by dehydration of boronic acids, while it is also known to be readily hydrolyzed to boronic acids under wet conditions. Therefore, hydrolysis is one of major problems for boroxine‐based architectures and materials, although they have self‐healing properties that can be restored simply by dehydration. In recent years, interesting studies have been reported to improve the hydrostability of boroxines, with some boroxines being stable even in water. This review categorizes and summarizes the findings on the enhancement of the hydrostability of boroxines according to the methods used.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400683"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622726","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. Jira Jongcharoenkamol , Rujiporn Saewa , Atchariya Intasri , Pariya Atawong , Phanupong Changtor , Dr. Kittisak Buddhachat , Dr. Sutthichat Kerdphon
{"title":"Commercial Copper‐Catalyzed Aerobic Oxidative Synthesis of 4H‐3,1‐Benzoxazine and Their Effects on Anti‐Inflammatory Genes Expression","authors":"Dr. Jira Jongcharoenkamol , Rujiporn Saewa , Atchariya Intasri , Pariya Atawong , Phanupong Changtor , Dr. Kittisak Buddhachat , Dr. Sutthichat Kerdphon","doi":"10.1002/ajoc.202400609","DOIUrl":"10.1002/ajoc.202400609","url":null,"abstract":"<div><div>A facile green synthesis of the anti‐inflammatory gene expression of 4<em>H</em>‐3,1‐benzoxazine was developed under a commercial copper catalytic system. Benzoxazines were synthesized from 2‐aminobenzyl alcohols and aromatic aldehydes including heterocyclic aromatic aldehydes using an economical commercially available copper(I)iodide (CuI) as a catalyst in the presence of the base, <sup><em>t</em></sup>BuOK. Target products were achieved in moderate to high yields with up to 75 % isolated yield. 4<em>H</em>‐3,1‐Benzoxazine enabled down‐regulation of inflammatory gene expression including tumor necrosis factor‐α (TNF‐<em>α</em>), inducible nitric oxide synthase (iNOS), cyclooxygenase‐2 (COX‐2), and interleukin‐1<em>β</em> (IL‐1<em>β</em>) in the lipopolysaccharide (LPS)‐stimulated RAW 264.7 macrophage cell line using a real‐time quantitative polymerase chain reaction (RT‐qPCR) comparable to anti‐inflammatory drug, dexamethasone. These results demonstrated that 4<em>H</em>‐3,1‐Benzoxazines possess the potential capability of anti‐inflammation.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400609"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622363","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}