Journal of Heterocyclic Chemistry最新文献

{"title":"","authors":"","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 5","pages":"905-912"},"PeriodicalIF":2.0,"publicationDate":"2026-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148064777","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Correction to “Synthesis and Biological Evaluation of Some Novel 3-Thioether-Linked 1,2,4-Triazole-Furoate Hybrids”","authors":"","doi":"10.1002/jhet.70152","DOIUrl":"https://doi.org/10.1002/jhet.70152","url":null,"abstract":"<p>S. Cai, Y. Zeng, H. Liu, et al., “Synthesis and Biological Evaluation of Some Novel 3-Thioether-Linked 1,2,4-Triazole-Furoate Hybrids,” <i>Journal of Heterocyclic Chemistry</i> 62, no. 11 (2025): 1595–1607, https://doi.org/10.1002/jhet.70091.</p><p>We apologize for this error.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.70152","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147566064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis, Bioactivity Evaluation, Molecular Docking, ADMET, and Drug-Likeness Studies of 4-Chromanone Derivatives Containing a Thiosemicarbazone Moiety as Potential Antioxidants and α-Glucosidase Inhibitors","authors":"Tiantian Zhuang,&nbsp;Wenmin Pan,&nbsp;You Zhang,&nbsp;Yongxiang Wu,&nbsp;Xiang Wang,&nbsp;Pei Li","doi":"10.1002/jhet.70146","DOIUrl":"https://doi.org/10.1002/jhet.70146","url":null,"abstract":"<div>\u0000 \u0000 <p>In this study, a novel series of 4-chromanone derivatives bearing a thiosemicarbazone moiety was rationally designed and efficiently synthesized. The structures of all newly obtained compounds were thoroughly characterized via various spectroscopic methods. The biological evaluation focused on their in vitro antioxidant activity and inhibitory effects against α-glucosidase. The biological evaluation revealed that several derivatives displayed notable antioxidant and enzyme inhibitory properties. In particular, compound (<i>E</i>)-2-(chroman-4-ylidene)-<i>N</i>-methylhydrazine-1-carbothioamide (<b>3a</b>) exhibited remarkable ABTS free radical scavenging ability, achieving an IC₅₀ of 3.76 μg/mL—outperforming the reference standard trolox, which showed an IC₅₀ of 8.04 μg/mL. Additionally, compound (<i>E</i>)-<i>N</i>-(2-(chroman-4-ylidene)hydrazine-1-carbonothioyl)benzamide (<b>3j</b>) emerged as a highly effective inhibitor of α-glucosidase, with an IC₅₀ value of 20.17 μg/mL, markedly lower than that of acarbose (237.48 μg/mL), indicating superior inhibitory potency. Molecular docking simulations demonstrated that compound <b>3a</b> interacts with the active site of NADPH oxidase (PDB: 2CDU) through van der Waals forces, π–sulfur, and π–alkyl contacts. In contrast, compound <b>3j</b> engaged more extensively with the catalytic pocket of human intestinal α-glucosidase (PDB: 3TOP), forming multiple interactions such as van der Waals, electrostatic attractions, conventional hydrogen bonds, π–π T-shaped, and π–alkyl bonds. ADMET profiling and drug-likeness assessments indicated that these lead compounds exhibit acceptable safety profiles and favorable physicochemical characteristics, aligning well with criteria for prospective therapeutic agents. To the best of our knowledge, this study presents the first comprehensive report on the synthesis, characterization, and biological assessment of this class of 4-chromanone derivatives bearing a thiosemicarbazone moiety.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"454-462"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563286","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Novel Tetraphenylporphyrin-Modified Pyrazolylazobenzene Derivative as Photoswitch: Design, Synthesis, and Photoswitching Behavior Research Combined With Controllable Fluorescence Properties","authors":"Chen Chen,&nbsp;Siyi Wei,&nbsp;Haoran Hu,&nbsp;Chengguo Sun,&nbsp;Chao Gao,&nbsp;Chong Zhang,&nbsp;Bingcheng Hu","doi":"10.1002/jhet.70148","DOIUrl":"https://doi.org/10.1002/jhet.70148","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel photochromic azoporphyrin compound was designed and synthesized, featuring a covalent linkage through an amide bond. The compound, designated as 5,10,15-triphenyl-20-{4-[4-(2-(3,5-dimethyl-1<i>H</i>-pyrazol-4-yl))diazenyl]benzamido}phenylporphyrin (<b>TPP-AAP</b>), incorporates an azo-functional group that confers photochromic properties. Its molecular structure and photochromic properties were characterized using NMR spectroscopy, UV–vis spectroscopy, and fluorescence spectroscopy. Upon the addition of a weak base (Na₂CO₃), the azo unit of <b>TPP-AAP</b> underwent <i>trans→cis</i> isomerization upon irradiation at 254 nm UV light; the reverse process (<i>cis→trans</i>) could be induced by subsequent irradiation with 450 nm visible light. The compound maintained stable antifatigue performance after multiple cycles. Fluorescence spectral analysis revealed that upon UV irradiation, the intense Q(0,0) emission band at 652 nm was significantly quenched. Concurrently, the Q(0,1) band at 718 nm underwent a blue shift to 706 nm, accompanied by an increase in intensity. These results demonstrate that the molecular conformational change significantly modulates the excited-state relaxation pathway. Consequently, the corresponding fluorescence signal provides an effective mechanism for nondestructive readout.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"526-536"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147567653","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Green Synthesis of Spirooxindoles: A One-Pot Domino Approach With Biological Screening","authors":"Aditi Boruah,&nbsp;Kalpajit Dutta,&nbsp;Mohit L. Deb,&nbsp;Pranjal K. Baruah","doi":"10.1002/jhet.70150","DOIUrl":"https://doi.org/10.1002/jhet.70150","url":null,"abstract":"<div>\u0000 \u0000 <p>A green and efficient one-pot domino approach has been developed for the synthesis of spirooxindole derivatives under catalyst-free conditions at room temperature in ethanol. The protocol offers several advantages, including operational simplicity, high atom economy, and good yields. The synthesized spirooxindoles were evaluated for their biological potential, revealing notable antioxidant activity for selected derivatives and promising antibacterial effects against Gram-positive strain, <i>Staphylococcus aureus</i>. This sustainable synthetic route provides a convenient strategy for generating biologically active spirooxindoles with potential pharmaceutical properties.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"504-511"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147565304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Utility of 3-Formylchromone in the Synthesis of Polyfunctional Nitrogenous Hybrids: Empowered by Anticancer Efficiency and Molecular Simulations","authors":"Alaa Ashraf El-Awady,&nbsp;Mohamed A. Ismail,&nbsp;F. H. Elghareeb,&nbsp;Eslam A. Ghaith","doi":"10.1002/jhet.70156","DOIUrl":"https://doi.org/10.1002/jhet.70156","url":null,"abstract":"<div>\u0000 \u0000 <p>Chromone derivatives are integral platforms of various medicinal agents and natural products. This study successfully presents a facile approach for the regioselective synthesis of diversely substituted binary <i>β</i>-hydroxy ketones and fused chromone scaffolds. These targets were achieved through direct treatment of 4-oxo-4<i>H</i>-chromene-3-carbaldehyde as a starting material with various heterocyclic systems and nucleophilic nitrogenous surrogates under mild conditions. Additionally, the utilized methodology demonstrated a broad substrate scope and good tolerance to various functionalities, utilizing ethanol as a top-tier green solvent. The cytotoxic profile of the synthesized hybrids against MCF-7 and HepG2 cell lines was debated, empowered by their DFT calculations and assessed drug-likeness analysis using Lipinski and Ghose filters. Interestingly, all synthesized hybrids adhered to the key physicochemical parameters of both Lipinski's and Ghose's rules, with zero violations. Generally, the results showed that the tested hybrids are more active against the MCF-7 cell line than the HepG2 cell line. Notably, compounds fused dihydropyrido[1,2,4]triazepine <b>11</b> and benzo[<i>d</i>]thiazole-6-sulfonamide <b>18</b> were the most effective compounds for MCF-7 (IC₅₀ = 3.96 and 7.67 μg/mL), whereby tetracyclic compounds dihydropyrido[1,2-<i>b</i>][1,2,4]triazepine <b>11</b> and <i>N</i>-(pyridin-2-yl)hydrazine-1-carbothioamide <b>18</b> were the most effective on HepG2 (IC₅₀ = 10.30 and 13.20 μg/mL) compared to <i>cis</i>-platin as standard drug (IC₅₀ = 8.60 on MCF-7 and 9.08 μg/mL on HepG2).</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"537-547"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147568352","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Regioselective 1,3-Dipolar Cycloaddition in the Vinyl-1,2,4-Triazole Series: A Straightforward Approach to Bis-Heterocycles","authors":"Sarra Ouni,&nbsp;Mohamed Oussama Zouaghi,&nbsp;Momtez Jmai,&nbsp;Abderrahmen Abdelli,&nbsp;Anne Gaucher,&nbsp;Jérôme Marrot,&nbsp;Hedi M'rabet,&nbsp;Youssef Arfaoui,&nbsp;Mohamed Lotfi Efrit,&nbsp;Damien Prim","doi":"10.1002/jhet.70143","DOIUrl":"https://doi.org/10.1002/jhet.70143","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel and straightforward approach to bis-heterocyclic compounds based on 1,2,4-triazoles and isoxazolidines is presented. The synthesis of these compounds is demonstrated through regioselective 1,3-dipolar cycloaddition reactions between 5-vinyl-1,2,4-triazole and nitrone derivatives. NMR and X-ray data allowed for determining the regioselectivity of the 1,3-dipolar cycloaddition and overall topology of bis-heterocyclic architectures. Additional theoretical calculations were carried out to analyze the critical bond-forming steps in constructing the heterocycle in more detail. Finally, the experimental and theoretical data correlation was studied using Hirschfeld surfaces.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"463-473"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563965","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Convenient Synthesis of Functionalized Spiropyrazolone-Fused Pyrazolo[1,5-c]Quinazolines via Catalyst-Free (3 + 2) Cycloaddition of Quinazoline-Derived Azomethine Imines With Arylidene Pyrazolones","authors":"Kai-Kai Wang,&nbsp;Wen-Jin Li,&nbsp;Yu Tang,&nbsp;Bo Hao,&nbsp;Jing Cao,&nbsp;Yi-Xuan Lu,&nbsp;Yu Xiao,&nbsp;Rongxiang Chen,&nbsp;Guo-Yi Yan","doi":"10.1002/jhet.70147","DOIUrl":"https://doi.org/10.1002/jhet.70147","url":null,"abstract":"<div>\u0000 \u0000 <p>In this paper, we developed a straightforward protocol for catalyst-free (3 + 2) cycloaddition between quinazoline-derived azomethine imines and arylidene pyrazolones to provide a series of spiropyrazolone-fused pyrazolo[1,5-<i>c</i>]quinazolines with yields ranging from moderate to good. These products possess three contiguous stereocenters, including a quaternary carbon center, and exhibit excellent regio- and diastereoselectivity (up to &gt; 25:1 dr). Moreover, this approach entails the utilization of readily accessible starting materials, encompasses a wide range of substrates, operates under mild reaction conditions, and offers the advantages of simple operational procedures and 100% atom economy. Additionally, the novel privileged structures incorporating spiropyrazolone and pyrazolo[1,5-<i>c</i>]quinazoline motifs demonstrate potential to be MEP1B inhibitors through a molecular docking study. The structural framework and relative configuration of the representative product were conclusively determined through single-crystal x-ray diffraction analysis.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"483-491"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147564472","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Magnetically Recoverable CuFe2O4 Catalyzed Direct Synthesis of Phenoxypyrimidines From Arylboronic Acids and Chloropyrimidines: A Heterogeneous Avenue","authors":"Rei Star,&nbsp;Spandan Saikia,&nbsp;Amar Jyoti Bhuyan,&nbsp;Shamima Hussain,&nbsp;Dimpul Konwar,&nbsp;Lakhinath Saikia","doi":"10.1002/jhet.70145","DOIUrl":"https://doi.org/10.1002/jhet.70145","url":null,"abstract":"<div>\u0000 \u0000 <p>Majority of the established procedures of synthesizing phenoxypyrimidines employ phenols and their simple salts as one of the substrates. However, phenols are toxic and can initiate secondary and tertiary burns when come into direct contact with the skin. Recently, our research group developed a very efficient homogeneous reaction protocol for cascade synthesis of phenoxypyrimidines starting from chloropyrimidines and arylboronic acids that could avoid use of phenols as substrate in presence of Cu(NO₃)₂•H₂O as a catalyst and DABCO as a ligand. The current work describes our first effort to develop a heterogeneous reaction protocol for the same. Magnetically active CuFe₂O₄ nanoparticles were prepared and checked for the purpose. CuFe₂O₄ nanoparticles prepared in presence of 1 wt.% of cetyltributylammonium-bromide (CTAB) as surfactant have been found effective to carry out the transformation in aqueous medium. Generality of the developed protocol has been demonstrated by synthesizing 15 numbers of phenoxypyrimidines. The catalyst system can be recovered very easily, and it is reused up to 4th run without any significant loss in activity. While laboratory prepared CuFe₂O₄ nanoparticles were characterized using FT-IR, XRD, and SEM–EDX analyses, all the synthesized compounds were characterized using ¹H and ¹³C NMR spectroscopy.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"474-482"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147564473","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Facile Access to Benzofuro-Fused-Azeto[1,2-a]Benzimidazoles as Promising Inhibitors of M. tuberculosis H37Rv","authors":"Rachana Upadhyay,&nbsp;Amit B. Patel","doi":"10.1002/jhet.70149","DOIUrl":"https://doi.org/10.1002/jhet.70149","url":null,"abstract":"<div>\u0000 \u0000 <p>A highly efficient Buchwald-Hartwig-type intramolecular C–N bond cyclization strategy was developed, enabling the facile annulation of 3-chloro-benzofuran-2-carbaldehyde with various substituted phenylenediamines to form a novel series of benzofuro-fused-azeto[1,2-<i>a</i>]benzoimidazoles. The Pd₂(dba)₃/XPhos/Cs₂CO₃ catalytic system efficiently delivered desired tetracyclic derivatives in excellent yield of up to 87%. The protocol demonstrates high synthetic efficiency, broad functional group tolerance, and wide substrate scope, highlighting its practical scalability. Synthesized derivatives were evaluated for their in vitro antimycobacterial activity against the <i>Mycobacterium tuberculosis</i> H₃₇Rv strain. Among them, analogs functionalized with unsubstituted benzimidazole, fluoro, benzophenone, and pyridyl groups demonstrated potent activity with MIC values of 3.12 μg/mL, respectively. Structure–activity relationship studies further reveal how specific functional group variations modulate the antimycobacterial potency of the compounds, highlighting their potential as powerful inhibitors of <i>M. tuberculosis</i> H₃₇Rv.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 3","pages":"492-503"},"PeriodicalIF":2.0,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147564474","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}