Journal of Heterocyclic Chemistry最新文献_第5页

Synthesis, Antimicrobial Activities, and Docking Simulations of Novel Hybrid Molecules Based on Bis-Thiazole Linked to a Pyridine Core 基于双噻唑-吡啶核的新型杂化分子的合成、抗菌活性和对接模拟

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-04-08 DOI: 10.1002/jhet.70196

Nahed Nasser Eid El-Sayed, Huda Kamel Mahmoud, Ahmed H. M. Elwahy, Mona M. Soliman, Ismail A. Abdelhamid, Hadeer M. Diab

{"title":"Synthesis, Antimicrobial Activities, and Docking Simulations of Novel Hybrid Molecules Based on Bis-Thiazole Linked to a Pyridine Core","authors":"Nahed Nasser Eid El-Sayed, Huda Kamel Mahmoud, Ahmed H. M. Elwahy, Mona M. Soliman, Ismail A. Abdelhamid, Hadeer M. Diab","doi":"10.1002/jhet.70196","DOIUrl":"https://doi.org/10.1002/jhet.70196","url":null,"abstract":"<div>\u0000 \u0000 Bacterial infections are increasingly emerging as a major worldwide concern, causing significant illness and mortality, especially in developing countries. Antimicrobial resistance poses a threat to global public health and advancement. The growing incidence of antibiotic-resistant bacteria emphasizes the need to find new approaches to fight them with different antimicrobial agents, as current treatments are becoming less effective. Heterocycles are vital in contemporary drug discovery and development. Recent progress in synthetic techniques enables the swift creation of many functionalized heterocyclic compounds, broadening the variety of drug-like materials available for drug discovery. In this context, a series of new bis-thiazole derivatives incorporating a pyridine core was efficiently synthesized. The compounds were obtained in good yields through the reaction of suitable α-haloketones or 2-α-keto-hydrazonoyl chlorides with the corresponding bis(hydrazinecarbothioamide) in dioxane under reflux conditions. The structures of the novel compounds were confirmed via elemental analyses and spectral data. The antibacterial effect of the newly synthesized compounds was evaluated against various bacterial strains. Compound 8a exhibited the highest antibacterial activity against Staphylococcus aureus (25.33 mm inhibition zone), while most tested compounds showed negligible antifungal effect. The minimum inhibitory concentrations (MICs) of the tested compounds against the bacterial species ranged from 4 to 28 mg/mL. Compound 13c showed a binding score of ∆G = −7.4 kcal/mol, forming 12 key interactions in the molecular docking study, indicating a strong affinity with the target protein. Notably, fluconazole demonstrated antifungal activity against Aspergillus niger and Aspergillus terreus.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 6","pages":"1042-1057"},"PeriodicalIF":2.0,"publicationDate":"2026-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148247839","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}

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Design, Synthesis, and Insecticidal Activities of Imidazo[4,5-b]Pyridine Compounds Containing Uracil Fragment 含尿嘧啶片段咪唑[4,5-b]吡啶类化合物的设计、合成及其杀虫活性

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-03-26 DOI: 10.1002/jhet.70191

Maoxin Sun, Mingming Dang, Denghui Deng, Liang Lv, Yu Yan, Hang Gong, Minhua Liu

{"title":"Design, Synthesis, and Insecticidal Activities of Imidazo[4,5-b]Pyridine Compounds Containing Uracil Fragment","authors":"Maoxin Sun, Mingming Dang, Denghui Deng, Liang Lv, Yu Yan, Hang Gong, Minhua Liu","doi":"10.1002/jhet.70191","DOIUrl":"https://doi.org/10.1002/jhet.70191","url":null,"abstract":"<div>\u0000 \u0000 As a novel class of nitrogen-containing heterocyclic compounds, imidazopyridine uracils serve as the core scaffold in this study, where 16 derivatives were designed and synthesized with oxazosulfuron as the lead compound. The chemical structures of the target compounds were fully characterized and confirmed by proton nuclear magnetic resonance spectroscopy (1H NMR), carbon-13 nuclear magnetic resonance spectroscopy (13C NMR), and high-resolution mass spectrometry (HRMS). Nilaparvata lugens, Plutella xylostella, and Mythimna separata were selected as the test insects, and the insecticidal activities of the target compounds were determined in this research. Especially, compound 8a showed a mortality rate of 77.8% against N. lugens at 10 mg/L, which was superior to the activity of oxazosulfyl under the same conditions (51.9% mortality at 10 mg/L). In addition, compound 9j exhibited a mortality rate of 25.0% against M. separata at a concentration of 1 mg/L, which was superior to that of oxazosulfyl under the same conditions (0% mortality at 1 mg/L). This study is intended to provide a theoretical reference for the subsequent research and industrial development of this class of novel insecticides.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 6","pages":"997-1003"},"PeriodicalIF":2.0,"publicationDate":"2026-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148247820","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}

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Isolation and Structural Characterization of Se-Hügerschoff Intermediates Derived From 4-Bromoaniline 4-溴苯胺衍生se - h<s:1> gerschoff中间体的分离与结构表征

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-04-02 DOI: 10.1002/jhet.70195

Adam W. E. Stewart, Tom Fellows, Lucy Li, Craig J. Morton, Glen P. Carter, Jonathan M. White

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Highly Diastereo- and Regioselective Synthesis of Spiropyrazole-Cyclopropanes via All-Carbon (2 + 1) Annulations of Acyclic Conjugated Imines With 4-Halo Pyrazolones 四环吡唑酮与无环共轭亚胺全碳（2 + 1）环合成螺吡唑环丙烷的高度非立体选择性和区域选择性

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-03-11 DOI: 10.1002/jhet.70188

Kai-Kai Wang, Xia-Shi Gao, Zi-Yue Qi, Miao Xue, Xiao-Ran Wang, Bo-Wen Zhang, Yi-Fan Zhang, Rongxiang Chen, Guo-Yi Yan

{"title":"Highly Diastereo- and Regioselective Synthesis of Spiropyrazole-Cyclopropanes via All-Carbon (2 + 1) Annulations of Acyclic Conjugated Imines With 4-Halo Pyrazolones","authors":"Kai-Kai Wang, Xia-Shi Gao, Zi-Yue Qi, Miao Xue, Xiao-Ran Wang, Bo-Wen Zhang, Yi-Fan Zhang, Rongxiang Chen, Guo-Yi Yan","doi":"10.1002/jhet.70188","DOIUrl":"https://doi.org/10.1002/jhet.70188","url":null,"abstract":"<div>\u0000 \u0000 A straightforward, diastereo- and regioselective synthesis of spiro-cyclopropane-pyrazolone compounds was achieved via all-carbon (2 + 1) cycloaddition reactions between acyclic conjugated imines and 4-halo pyrazolones. The reactions proceeded with moderate to high yields (up to 92% yields), and displayed outstanding regio- and diastereoselectivity (in all cases > 25:1 dr). As a result, the desired spirocyclic compounds, which incorporate both a pyrazolone and a cyclopropane moiety, were obtained as single diastereoisomers. Additionally, the spiropyrazole-cyclopropanes which possess three contiguous stereocenters including a quaternary carbon center, have demonstrated potential ALDH1A1 inhibitor, as substantiated by a molecular docking study. The structure and relative configuration of the product were unambiguously determined by single-crystal x-ray diffraction analysis.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 6","pages":"938-947"},"PeriodicalIF":2.0,"publicationDate":"2026-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148247800","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}

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Efficient Synthesis of 1,4,2-Dioxazepines via [4+3] Cyclization of p-QMs With In Situ Generated N-Electron-Withdrawing Group Nitrones 用原位生成n-吸电子基氮酮[4+3]环化p-QMs高效合成1,4,2-二恶氮卓类药物

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-04-10 DOI: 10.1002/jhet.70198

Li-Wen Shen, Ci Ding, Song Hu, Guang-Wei Wang, Yun-Qing Jia, Min Xiang

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Regioselective Multicomponent Hantzsch-Like Synthesis of Novel Pentaza-Cyclopenta[b]Anthracene-Dione-Phenoxyacetamide Hybrids 新型五叠-环五叠蒽-二酮-苯氧乙酰胺杂合体的区域选择性多组分类hantzsch合成

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-03-10 DOI: 10.1002/jhet.70183

Doaa Hassan Ali, Hadeer M. Diab, Ahmed H. M. Elwahy, Tayseer A. Abdallah, Hamdi M. Hassaneen, Ehab M. Zayed, Ismail A. Abdelhamid

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TiO2-Catalyzed One-Pot Synthesis, Molecular Docking, and Anticancer Activity of Novel Quinoline-Pyrazole Hybrid Derivative 新型喹啉-吡唑杂化衍生物的tio2催化一锅合成、分子对接及抗癌活性研究

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-04-07 DOI: 10.1002/jhet.70190

Dharmesh K. Katariya, Jay B. Maheta, Chandani S. Gori, Pankaj P. Solanki, Bharat R. Kataria, Manish K. Shah, Ranjan C. Khunt, Yogesh O. Bhola

{"title":"TiO2-Catalyzed One-Pot Synthesis, Molecular Docking, and Anticancer Activity of Novel Quinoline-Pyrazole Hybrid Derivative","authors":"Dharmesh K. Katariya, Jay B. Maheta, Chandani S. Gori, Pankaj P. Solanki, Bharat R. Kataria, Manish K. Shah, Ranjan C. Khunt, Yogesh O. Bhola","doi":"10.1002/jhet.70190","DOIUrl":"https://doi.org/10.1002/jhet.70190","url":null,"abstract":"<div>\u0000 \u0000 A series of novel quinoline-pyrazole hybrid derivatives (4a–j) were synthesized via a rapid, eco-friendly one-pot three-component condensation using TiO2 nanoparticles as catalysts. The reaction proceeded efficiently at room temperature in methanol, yielding products within 5–10 min. All compounds were evaluated for cytotoxicity against MCF-7 and HepG2 cancer cell lines using the MTT assay. Compound 4e (4-OCH₃) exhibited the most potent activity, with IC50 values of 9.1 ± 0.5 μM (MCF-7) and 24.2 ± 0.7 μM (HepG2), comparable to doxorubicin (10.6 ± 0.2 μM for MCF-7). Structure–activity relationship analysis revealed that electron-donating groups (4-OCH3, 3-OCH3, and 4-CH3). Molecular docking studies against EGFR (1 M17) and VEGFR2 (3VHE) showed that 4e exhibited superior binding affinity (−6.34 and −7.51 kcal/mol) compared with erlotinib and sorafenib, with key hydrogen bonds and hydrophobic interactions in the ATP-binding sites. These findings establish quinoline-pyrazole hybrids as promising dual EGFR/VEGFR2 inhibitors, with compound 4e being a lead candidate for anticancer drug development.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 6","pages":"1030-1041"},"PeriodicalIF":2.0,"publicationDate":"2026-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148247830","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}

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Substrate-Controlled Regiodivergent Annulation for Construction of Highly Substituted Cyclopropanes 底物控制的区域发散环法制备高取代环丙烷

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-03-12 DOI: 10.1002/jhet.70187

Kai-Kai Wang, Qing Xu, Xia-Shi Gao, Rongxiang Chen, Guo-Yi Yan

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Synthesis, Biological Activity, and Docking Studies of the Fused Pyrazoline and Thiazole Hybrids 吡唑啉与噻唑融合杂化物的合成、生物活性及对接研究

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-04-07 DOI: 10.1002/jhet.70184

Nagma Banu Holalgod Abbas, Balakrishna Kalluraya, Gunashree Boraiah Shivanna, Mahesha, Lokanath Neratur Krishnappagowda

{"title":"Synthesis, Biological Activity, and Docking Studies of the Fused Pyrazoline and Thiazole Hybrids","authors":"Nagma Banu Holalgod Abbas, Balakrishna Kalluraya, Gunashree Boraiah Shivanna,  Mahesha, Lokanath Neratur Krishnappagowda","doi":"10.1002/jhet.70184","DOIUrl":"https://doi.org/10.1002/jhet.70184","url":null,"abstract":"<div>\u0000 \u0000 Heterocyclic compounds containing thiazole embedded with pyrazoline moieties were designed via the Claisen-Schmidt reaction followed by the condensation reaction with substituted phenacyl bromides. Structures of the synthesized compounds (5a–l) were confirmed by FTIR, 13C-NMR, 1H-NMR, and mass spectral analysis. All the compounds were screened for in vitro antimicrobial activity against Gram-positive and Gram-negative bacterial and fungal strains. Among the synthesized compounds, most of them showed good to moderate antimicrobial activity against Escherichia coli at different concentrations. The compound 4,5-dihydro-5-(4-nitrophenyl)-1-(5-phenylthiazol-2-yl)-3-(4-(prop-2-ynyloxy)phenyl)-1H-pyrazole (5i) and 4,5-dihydro-1-(5-(4-methoxyphenyl)thiazol-2-yl)-5-(4-nitrophenyl)-3-(4-(prop-2-ynyloxy)phenyl)-1H-pyrazole (5 k) showed inhibitory potency against Candida albicans. Molecular docking studies were performed to check the insights of the activity experimentally and theoretically, which supported the in vitro activity results. The binding energy of −11.2 Kcal/mol for the compound 5-(4-fluorophenyl)-4,5-dihydro-3-(4-(prop-2-ynyloxy)phenyl)-1-(5-p-tolylthiazol-2-yl)-1H-pyrazole (5g) showed the greater interaction towards the target Escherichia coli MurB enzyme (PDB code: 2MBR). The present study emphasizes the importance of the pyrazoline-thiazole moiety in synthetic and medicinal chemistry with potential pharmacological activity.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 6","pages":"1018-1029"},"PeriodicalIF":2.0,"publicationDate":"2026-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148247829","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}

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Pyrimidines Annulated Pyridine and Pyrimidine at Face d (2017–2025): A Comprehensive Survey of Synthetic Methodologies (Part 1) 环吡啶和面d嘧啶（2017-2025）：合成方法综述（上）

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Journal of Heterocyclic Chemistry Pub Date : 2026-06-14 Epub Date: 2026-03-15 DOI: 10.1002/jhet.70186

Al-Shimaa Badran, Zeinab Hussain, Kholoud Ahmed, Yassin A. Gabr, Hassan A. Allimony, Mohamed Abdel-Megid, Magdy A. Ibrahim

{"title":"Pyrimidines Annulated Pyridine and Pyrimidine at Face d (2017–2025): A Comprehensive Survey of Synthetic Methodologies (Part 1)","authors":"Al-Shimaa Badran, Zeinab Hussain, Kholoud Ahmed, Yassin A. Gabr, Hassan A. Allimony, Mohamed Abdel-Megid, Magdy A. Ibrahim","doi":"10.1002/jhet.70186","DOIUrl":"https://doi.org/10.1002/jhet.70186","url":null,"abstract":"<div>\u0000 \u0000 Pyrimidine is a fundamental heterocyclic scaffold with broad significance in chemical biology and pharmaceutical research. Although numerous reviews have focused on the biological activities of pyrimidine derivatives, comprehensive analyses dedicated specifically to pyrimidines fused at the face d position remain limited. In this context, face d-annulation refers to the fusion of additional rings onto the C4–C5 edge of the pyrimidine core, generating structurally diverse condensed systems. This review provides a comprehensive literature survey covering the period from 2017 to 2025 and focuses exclusively on the synthetic development of pyrimidine frameworks annulated at face d. This review systematically organizes reported synthetic methodologies, discusses substrate scope and reaction conditions, and presents proposed mechanistic pathways where available. Particular emphasis is placed on pyridopyrimidines, pyrimidopyrimidines, and related fused heterocyclic systems constructed through diverse strategies. Unlike previous general reviews on pyrimidine synthesis, this work specifically concentrates on face d-fused pyrimidine systems, thereby providing a focused and structured reference for researchers interested in this distinct structural class. The analysis presented herein aims to support further synthetic innovation and broaden the applications of pyrimidine-based fused scaffolds.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 6","pages":"958-981"},"PeriodicalIF":2.0,"publicationDate":"2026-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148247767","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}

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