Faezeh Zoghi-Paydar, Mahdiyeh Derakhshideh, Mohammad Azimi, Ahmad Ebadi, Gholamabbas Chehardoli, Mohammad Ali Faramarzi, Somayeh Mojtabavi, Mohammad Mahdavi, Zahra Najafi
{"title":"Novel Resorcinol-Based 2-Amino-4H-chromene-3-carbonitrile Derivatives as α-Glucosidase Inhibitors: Synthesis, In Vitro Evaluation, and Molecular Dynamics Simulation Studies","authors":"Faezeh Zoghi-Paydar, Mahdiyeh Derakhshideh, Mohammad Azimi, Ahmad Ebadi, Gholamabbas Chehardoli, Mohammad Ali Faramarzi, Somayeh Mojtabavi, Mohammad Mahdavi, Zahra Najafi","doi":"10.1002/ajoc.202500430","DOIUrl":"10.1002/ajoc.202500430","url":null,"abstract":"<p>A novel series of resorcinol-based 2-amino-4<i>H</i>-chromene-3-carbonitrile derivatives was synthesized and assessed against yeast α-glucosidase enzyme. All synthesized compounds showed significant inhibitory activities toward the enzyme with IC<sub>50</sub> values ranging from 44.0 ± 1.2 to 551.5 ± 1.6 µM in comparison with acarbose, as a standard agent (IC<sub>50</sub> = 750.0 µM). Among them, 2-amino-4-(4-((4-bromobenzyl)oxy)-3-methoxyphenyl)-7-hydroxy-4H-chromene-3-carbonitrile (<b>6e</b>) indicated the most potent inhibitory activity. The kinetic study indicated that the compound <b>6e</b> acts as a competitive α-glucosidase inhibitor. Afterward, molecular docking and molecular dynamics (MD) simulations of the <i>R</i>- and <i>S</i>-enantiomers of compound <b>6e</b> against a homology-modeled enzyme confirmed significant interactions with the catalytic residues. Additionally, in silico ADMET predictions showed that resorcinol-based 2-amino-4<i>H</i>-chromene-3-carbonitrile derivatives possess acceptable pharmacokinetic properties and therapeutic potential for the future treatment of type 2 diabetes mellitus (T2DM).</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057884","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}
Bipin Khanal, Kanokwan Jaithum, Mark Aldren M Feliciano, Brian Gold
{"title":"Catalytic Ullmann-Type N-Arylation to Access Medicinally Important SuFEx-able Pyrazolo[1,5-a]Quinoxalinones","authors":"Bipin Khanal, Kanokwan Jaithum, Mark Aldren M Feliciano, Brian Gold","doi":"10.1002/ajoc.202500474","DOIUrl":"10.1002/ajoc.202500474","url":null,"abstract":"<p>Pyrazole-fused quinoxalines provide an attractive structural motif for medicinal chemistry and have inspired the development of novel synthetic methods. This work details a concise methodology for the synthesis of a new class of pyrazolo[1,5-<i>a</i>]quinoxaline-4-ones, where the incorporation of a sulfonyl fluoride enables sulfur(IV) fluoride exchange (SuFEx) chemistry. This synthetic approach opens the door for the rapid diversification of these fused heterocycles, providing a powerful strategy for the expansion of chemical space and the development of novel bioactive compounds.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057883","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}
Yujie Cao, Arnav Kacker, Prof. Dr. Kevin G. M. Kou
{"title":"Piano-Stool Rhodium(V) and Rhodium(IV) Intermediates in C─H Functionalization and B─H Functionalization: Mechanistic Insights and Emerging Reactivity","authors":"Yujie Cao, Arnav Kacker, Prof. Dr. Kevin G. M. Kou","doi":"10.1002/ajoc.202500559","DOIUrl":"10.1002/ajoc.202500559","url":null,"abstract":"<p>Rhodium(III) catalysis is widely adopted for C─H functionalization due to its operational simplicity and broad substrate scope, with the Rh(III)/(I) catalytic manifold being the most commonly encountered. However, an increasing number of studies associate new or enhanced reactivity with high-valent Rh(V) and Rh(IV) intermediates. This review compiles the evidence for both, with a focus on methodologies that proceed via the Rh(III)/Rh(IV)/Rh(II) catalytic cycle. While Rh(V)-mediated catalysis is supported by computational studies, experimental validation remains limited. In contrast, catalysis involving Rh(IV) intermediates is supported by both computational and experimental evidence.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500559","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057885","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}
Eden Sinchana D Souza, Sumanth Hegde, Aatika Nizam, Vasantha Veerappa Lakshmaiah
{"title":"Advancement in the Synthetic Methodologies for C─O and C─S Cross-Coupling Reactions via Homogeneous Catalysis: A Decade of Progress","authors":"Eden Sinchana D Souza, Sumanth Hegde, Aatika Nizam, Vasantha Veerappa Lakshmaiah","doi":"10.1002/ajoc.202500266","DOIUrl":"10.1002/ajoc.202500266","url":null,"abstract":"<p>Carbon-heteroatom coupling reactions are a very crucial category of transformations in organic synthesis, enabling the creation of a wide range of chemical structures essential for pharmaceuticals, agrochemicals, and material science. These reactions involve the formation of a bond between carbon and heteroatoms such as nitrogen, sulfur, and oxygen, which play a vital role in the functionalization of organic molecules. Various pharmaceutical drug molecules have a carbon-heteroatom bond as the core component. Therefore, the synthesis of such molecules has garnered considerable attention in recent years. This review explores advancements in methodologies and catalytic systems that promote C─X (where X = O, S) bond formation, with a focus on cross-coupling reactions involving sulfur and oxygen. We highlight the development of different novel catalysts, transition metals, transition metal-free methods, and different sulfur and oxygen sources used for this conversion that provided greater efficiency, selectivity, and functional group tolerance over the decade (2014–2024). Also, this review aims to provide the current trends as well as the future scope in carbon-heteroatom coupling reactions.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057882","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}
Chinmay Thakkar, Valmik P. Jejurkar, Mansi Singh, Monalisha Debnath, Anjali Tripathi, Purav Badani, Rohit Srivastava, Dr. Satyajit Saha
{"title":"Triarylmethane (TRAM)-Based Aggregation-Induced Emissive Luminogen with Enhanced Oxidation Stability and Bio-Imaging Capability","authors":"Chinmay Thakkar, Valmik P. Jejurkar, Mansi Singh, Monalisha Debnath, Anjali Tripathi, Purav Badani, Rohit Srivastava, Dr. Satyajit Saha","doi":"10.1002/ajoc.202500217","DOIUrl":"10.1002/ajoc.202500217","url":null,"abstract":"<p>Fluorescent technologies are driving a sustainable, eco-friendly future by enhancing energy efficiency, reducing environmental impact, and promoting renewable resources. Recent efforts have focused on designing small molecules with tunable fluorescent behavior, with diverse heterocyclic molecules playing a key role. Traditional carbazole-derived fluorophores, while highly fluorescent in dilute solutions, often suffer from aggregation-caused quenching (ACQ) in high-concentration or aggregated states due to non-radiative decay pathways like π–π stacking. Additionally, the 3,6-positions of carbazole are prone to irreversible electrochemical dimerization and polymerization, limiting their use in organo-electronic materials. To address the emission quenching and oxidation vulnerability, we introduced new molecular rotors at these positions to enhance oxidation stability and restrict intramolecular motions in the aggregated state. We designed an AIEgen by appending distorted tetraphenyl ethene to the carbazole moiety, flanked by two dialkylmethane groups, using quinone-methide chemistry with FeCl<sub>3</sub> catalyst. The resulting luminogen, <b>MAS-01</b>, exhibited cyan emission in the solid-state with impressive aggregation-induced emission with a photoluminescence quantum yield of 20.54%. <b>MAS-01</b> also demonstrated cytotoxic behavior against HeLa cells, with an IC<sub>50</sub> value of 4.64 µg/mL, indicating concentration-dependent anti-metastatic potential. The luminogen uniformly entered the cytoplasm and showed nuclear co-localization, highlighting its bio-imaging capabilities even at low concentrations.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057797","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 Tang, Ming-Xing Lan, Hai-Na Ding, Xue-Qing Mou, Yun Zhang, Yong-Zheng Chen, Bao-Dong Cui
{"title":"Photocatalytic Reductive Borylation, Phosphonation, Sulfurization, and Selenization of Aryl Iodides to Access Aryl Borates, Aryl Phosphates, Aryl Sulfides, and Aryl Selenides","authors":"Juan Tang, Ming-Xing Lan, Hai-Na Ding, Xue-Qing Mou, Yun Zhang, Yong-Zheng Chen, Bao-Dong Cui","doi":"10.1002/ajoc.202500362","DOIUrl":"10.1002/ajoc.202500362","url":null,"abstract":"<p>A simple photoinduced radical borylation, phosphonation, sulfurization and selenization of various aryl iodides to construct the structurally diverse C-B/P/S/Se bonds has been developed. Using HCO<sub>2</sub>Na as the reductant, a wide range of aryl iodides including the substituted iodobenzenes, heteroaromatic iodides, aromatic iodides derived from the pharmaceutically active molecules could be utilized to react with the bis(pinacolato)diboron, triethyl phosphite, (RS)<sub>2</sub> or (RSe)<sub>2</sub> to obtain a variety of aryl borates, aryl phosphates, aryl sulfides and aryl selenides in general moderate to good yields.The advantage of this protocol is also highlighted by its no extra metal/photocatalyst, gram-scale synthesis and the further functional transformations of the products.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057795","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-Nitrotetralin Derivatives via NHC-Catalyzed Homoenolate Reactions","authors":"Aniruddh Pratap, Prof. Dr. Biswajit Maji","doi":"10.1002/ajoc.202500588","DOIUrl":"10.1002/ajoc.202500588","url":null,"abstract":"<p>We report herein a highly diastereo- and enantioselective homoenolate addition reaction to <i>E</i>-3-nitro-1,2-dihydronaphthalene via the NHC-bound azolium homoenolate pathway, affording 2-nitrotetralins in very good chemical yields. The key 2-nitrotetralin derivatives, featuring two adjoining stereocenters, exhibit structural resemblance to the serrulatane and amphilectane diterpene natural products and pharmaceutically relevant ingredients. This catalytic asymmetric process offers a broad substrate scope, accommodating a wide range of enals and nitroalkenes embedded in tetralin or chroman frameworks, thereby yielding 2-nitrotetralin and 3-nitrochroman derivatives with three contiguous stereocenters. Other important features include: (i) readily accessible nitroalkenes and enals, including commercially available NHC-catalyst; (ii) simplicity of the reaction conditions; and (iii) the formation of C<sub>3</sub>-nitro-containing tetralins and chroman cores with a high level of diastereo- and enantioselectivities (up to >99:1 dr and 95% ee), along with several powerful synthetic transformations and functionalizations.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057794","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}
Shilong Zhang, Prof. Jinwei Yuan, Prof. Meng Yan, Zhiyi Wang, Prof. Liangru Yang, Prof. Yongmei Xiao, Prof. Shouren Zhang, Prof. Lingbo Qu
{"title":"Photoredox-Catalyzed Difluoromethylation/Cyclization of N-Cyanamide Alkenes to Access Difluoromethylated Polycyclic Quinazolinones","authors":"Shilong Zhang, Prof. Jinwei Yuan, Prof. Meng Yan, Zhiyi Wang, Prof. Liangru Yang, Prof. Yongmei Xiao, Prof. Shouren Zhang, Prof. Lingbo Qu","doi":"10.1002/ajoc.202500591","DOIUrl":"10.1002/ajoc.202500591","url":null,"abstract":"<p>An efficient photoinduced radical cascade difluoromethylation/cyclization reaction of <i>N</i>-cyanamide alkenes has been developed. A diverse range of difluoromethylated quinazolinones have been synthesized with good yields and broad functional group tolerance. This photocatalytic protocol offers a facile and practical approach to accessing valuable polycyclic quinazolinone derivatives. Preliminary mechanistic studies suggest that the transformation proceeds via a radical pathway involving single electron transfer (SET).</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057799","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":"Sustainable Strategy to Access Fused Chromenoquinoline Analogues via Doebner–Von Miller-Type Reaction and Mechanistic Insights","authors":"Paranimuthu Panjacharam, Sabbasani Rajasekhara Reddy","doi":"10.1002/ajoc.70106","DOIUrl":"10.1002/ajoc.70106","url":null,"abstract":"<p>In this study, we report a metal- and oxidant-free synthesis of fused chromenoquinolines via an acetic acid-promoted Doebner–Von Miller-type reaction. This effective method allows substituted anilines to react with 4-chloro-2<i>H</i>-chromene-3-carbaldehydes in an eco-friendly way, facilitating the formation of new C─N and C─C bonds while building fused polycyclic heteroaromatic rings. This protocol is broadly applicable for the synthesis of diverse 6<i>H</i>-chromeno[4,3-<i>b</i>]quinolines, which serve as versatile scaffolds for the subsequent cross-coupling reactions and C(sp<sup>3</sup>)─H oxidation.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057798","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":"Copper-Mediated C(sp2)-S Coupling: a Strategy for the Preparation of S-Aryl Dithiocarbamates","authors":"Piyushkumar Satani, Sudha Soliya, Bharatkumar Prajapati, Kuldeep Joshi, Subrata Dutta, Togati Naveen","doi":"10.1002/ajoc.202500419","DOIUrl":"10.1002/ajoc.202500419","url":null,"abstract":"<p>We developed an efficient copper-mediated one-pot, three-component reaction for synthesizing <i>S-</i>aryl dithiocarbamates from aliphatic amines, phenylboronic acid, and carbon disulfide. This approach proceeds under mild, ambient conditions without requiring a base or additional additives, significantly reducing reaction time. Using easily accessible starting materials makes the process cost-effective and scalable, yielding high product quantities with minimal complexity. Due to its efficiency, simplicity, and versatility, this method represents a significant advancement in dithiocarbamate synthesis, with promising applications in organic and medicinal chemistry.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057800","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}