Journal of Heterocyclic Chemistry最新文献

Synthetic Strategies for C-Amino 1,2,3-Triazoles and Their Oxides: A Review

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-12 DOI: 10.1002/jhet.4920

Sofya P. Balabanova, Alexey A. Voronin, Aleksandr M. Churakov, Michael S. Klenov, Vladimir A. Tartakovsky

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Lewis Base Promoted [4+2] Annulation of o-Acylamino-Aryl Morita-Baylis-Hillman Carbonates With Isatylidene Malononitriles: Facile Access to Spiro[Indolin-3,2′-Quinoline] Frameworks

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-10 DOI: 10.1002/jhet.4919

Li-Wen Shen, Mao-Dan Luo, Wen-Yi Zhou, Yuan-Ying Luo, Min Xiang, Yun-Qing Jia, Shu-Pei Yuan, Guang-Wei Wang

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Coumarin Derivatives: Microwave Synthesis and Biological Properties—A Review 香豆素衍生物：微波合成与生物特性--综述

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-10 DOI: 10.1002/jhet.4918

Wissam Habibi, Soumaya Talbi, Salha Hamri, Abderrafia Hafid, Mostafa Khouili

{"title":"Coumarin Derivatives: Microwave Synthesis and Biological Properties—A Review","authors":"Wissam Habibi, Soumaya Talbi, Salha Hamri, Abderrafia Hafid, Mostafa Khouili","doi":"10.1002/jhet.4918","DOIUrl":"https://doi.org/10.1002/jhet.4918","url":null,"abstract":"<div>\u0000 \u0000 Many molecules called coumarins with very varied biological activities and widely used in the food, pharmaceutical, cosmetic, and medical industries. Their structure has a significant impact on their biological activity and their possible applications. Advanced synthesis frequently leads to an increase in the production of various chemical wastes. The amount of hazardous organic substances used and produced is reduced by the application of environmentally friendly synthesis techniques. Numerous techniques are employed in green chemistry, including the use of ionic liquids and deep eutectic solvents, solvent-free synthesis, mechanical synthesis, multicomponent reactions, ultrasound, and microwaves. These green synthesis techniques have been successfully applied to all common condensation reactions for the synthesis of coumarin, including the Perkin, Knoevenagel, Pechmann, Kostanecki-Robinson, and Reformansky reactions. These methods not only reduce the use and production of toxic chemicals, but also improve the yield, purity, and energy consumption of the product. This review summarizes the methods of microwave synthesis of coumarin derivatives, as well as their biological activities.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"2070-2096"},"PeriodicalIF":2.0,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860804","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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Visible Light Mediated CO2 Fixation Reactions to Produce Carbamates and Carbonates: A Comprehensive Review

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/jhet.4882

Asmita Goswami, Monika Verma, Ajay Thakur, Ruchi Bharti, Renu Sharma

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1,5-Diazocine-Based Diaryl Ketones: Design, Synthesis, and Optoelectronic Properties

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-04 DOI: 10.1002/jhet.4915

Anjitha Sebastian, Vibhu Darshan, Bijoy Nharangatt, Vijay Kumar Maka, Amrutham Linet, Simi Achankunju, Masaki Nagaoka, Shigeyuki Yagi, Narayanan Unni K. N., Ishita Neogi

{"title":"1,5-Diazocine-Based Diaryl Ketones: Design, Synthesis, and Optoelectronic Properties","authors":"Anjitha Sebastian, Vibhu Darshan, Bijoy Nharangatt, Vijay Kumar Maka, Amrutham Linet, Simi Achankunju, Masaki Nagaoka, Shigeyuki Yagi, Narayanan Unni K. N., Ishita Neogi","doi":"10.1002/jhet.4915","DOIUrl":"https://doi.org/10.1002/jhet.4915","url":null,"abstract":"<div>\u0000 \u0000 Three novel heterocyclic host based on diaryl ketone-tethered 1,5-diazocines were designed and synthesized for applications in phosphorescent organic light-emitting diodes (PhOLEDs). The hosts were derived by anchoring the naphthyl ketone (TBN), anthryl ketone (TBA), and phenanthryl ketone (TBP) to the 1,5-diazocine core. The materials were successfully characterized using spectroscopic techniques. TBN and TBP exhibited low external quantum efficiency of 1.5% and 1.9% when explored as hosts in PhOLED devices. Among the series, TBP exhibited the highest luminance of 4160 cd/m2, maximum luminance efficiency of 6.3 cd/A, and power efficiency of 3.21 lm/w, when doped with Ir(ppy)3 in PhOLED. Nevertheless to our surprise, TBA manifested the lowest device performance than other TBs as a host due to low carrier mobility caused by a highly twisted structure as deciphered from the comparative analysis of single-crystal structure that could impede carrier transport crucial for efficient electroluminescence. The outcomes of electroluminescence were validated and explained with analysis of single-crystal structure, and also with the aid of density functional theory.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"2040-2049"},"PeriodicalIF":2.0,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860014","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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N-Methoxy Pyrazole-4-Carboxamide Derivatives: Synthesis, Spectral Analyses, Antifungal Activity, In Silico Molecular Docking, ADMET, and DFT Studies

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-02 DOI: 10.1002/jhet.4903

Zi-Ting Luo, Bin Wang, Hong-Ke Wu, Li-Jing Min, Li-Qin Zhang, Xing-Hai Liu

{"title":"N-Methoxy Pyrazole-4-Carboxamide Derivatives: Synthesis, Spectral Analyses, Antifungal Activity, In Silico Molecular Docking, ADMET, and DFT Studies","authors":"Zi-Ting Luo, Bin Wang, Hong-Ke Wu, Li-Jing Min, Li-Qin Zhang, Xing-Hai Liu","doi":"10.1002/jhet.4903","DOIUrl":"https://doi.org/10.1002/jhet.4903","url":null,"abstract":"<div>\u0000 \u0000 Succinate dehydrogenase inhibitor (SDHI) is an important fungicide to control grain diseases. For this reason, a series of novel pyrazole-4-carboxamide derivatives with an N-methoxy group were designed and synthesized. All the target compounds were characterized by 1H NMR, 13C NMR, and HRMS. The compound 3c was further confirmed by X-ray diffraction, which crystallized in the triclinic system, space group P-1, Z = 2. The fungicidal activity results indicated that most of these compounds possessed good activity against Sclerotinia sclerotiorum at 50 ppm. Especially, compound 3h exhibited the best activity with the EC50 is 7.80 μg/mL, which is comparable with the positive control bixafen (EC50 = 6.70 μg/mL). Furthermore, the physicochemical properties, molecular docking simulation, ADMET analyses, DFT of compounds 3h, 3k and two commercial SDHIs, isoflucypram and pydiflumetofen, were investigated in this study.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"2015-2025"},"PeriodicalIF":2.0,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860106","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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Discovery of Promising Sulfadiazine Derivatives With Anti-Proliferative Activity Against Tumor Cell Lines 发现对肿瘤细胞株具有抗增殖活性的磺胺嘧啶衍生物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-02 DOI: 10.1002/jhet.4893

Reham A. Mohamed-Ezzat, Benson M. Kariuki, Rasha A. Azzam

{"title":"Discovery of Promising Sulfadiazine Derivatives With Anti-Proliferative Activity Against Tumor Cell Lines","authors":"Reham A. Mohamed-Ezzat, Benson M. Kariuki, Rasha A. Azzam","doi":"10.1002/jhet.4893","DOIUrl":"https://doi.org/10.1002/jhet.4893","url":null,"abstract":"<div>\u0000 \u0000 A novel series of pyrimidine sulfonamide derivatives was synthesized through a strategic approach involving the creation of substituted dihydropyrimidinyl-benzenesulfonamides and subsequent transformation into their chlorinated analogues. These compounds were then subjected to reactions with various amines and phenols, yielding unique substituted sulfapyrimidines. These novel structures integrated essential pharmacophores such as phenols, secondary amines, and benzenesulfonamide moieties, each contributing distinct biological potencies, chemical reactivity, and enhanced pharmacological features. In the pursuit of effective anticancer agents, the newly substituted pyrimidine sulfonamides were characterized using spectroscopic and x-ray diffraction techniques. The compounds were evaluated for their anti-proliferative potency against the NCI 60-cell lines panel, revealing that compound 7c exhibited significant growth inhibition across multiple cancer cell lines. Further assessment through MTT assay on HCT-116 and MCF-7 cell lines demonstrated cytotoxicity, while cell cycle analysis of MCF-7 cells treated with compound 7c revealed arrest at the S phase. Moreover, the effect of 7c on programmed cell death was evaluated using the Annexin V/PI apoptosis assay. The observed promising activity positions these pyrimidine-based scaffolds as potential candidates for future drug development, offering valuable insights for medicinal chemists engaged in the design and synthesis of anticancer drugs.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"1980-1998"},"PeriodicalIF":2.0,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860105","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}

引用次数: 0

Synthesis of Benzannulated Spiroketals Derived From Stigmasterol and Sitosterol by Pd-Catalyzed Spirocyclization. NMR and X-ray Characterization. Evaluation of Cytotoxicity and Anti-Inflammatory Activity 通过钯催化螺环化合成由赤霉醇和谷甾醇衍生的苯并螺环酮类化合物。核磁共振和 X 射线表征。细胞毒性和抗炎活性评估

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-02 DOI: 10.1002/jhet.4900

William H. Garcia-Santos, Martha C. Mayorquin-Torres, Nimsi Campos-Xolalpa, Salud Pérez-Gutiérrez, Marcos Flores-Álamo, Martín A. Iglesias-Arteaga

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Current Advances in Synthesis of Pyrazole Derivatives: An Approach Toward Energetic Materials

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-02 DOI: 10.1002/jhet.4904

Jaime Portilla

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Design, Synthesis, In Vitro Evaluation of New Tetrahydrooxazolo [5′,4′:4,5]Pyrimido[1,2-a]Azepinone Derivatives as Anticancer Agents

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/jhet.4907

Yan Zeng, Yan Ma, Li Xiao, Chao Niu, Lifei Nie

{"title":"Design, Synthesis, In Vitro Evaluation of New Tetrahydrooxazolo [5′,4′:4,5]Pyrimido[1,2-a]Azepinone Derivatives as Anticancer Agents","authors":"Yan Zeng, Yan Ma, Li Xiao, Chao Niu, Lifei Nie","doi":"10.1002/jhet.4907","DOIUrl":"https://doi.org/10.1002/jhet.4907","url":null,"abstract":"<div>\u0000 \u0000 A total of 48 tetrahydrooxazolo-[5′,4′:4,5]pyrimido[1,2-a]azepinones were designed and synthesized from a scaffold hopping approach. All compounds were confirmed by analysis using 1H NMR, 13C NMR, and HRMS techniques. The synthesized compounds were evaluated against the human cancer cell lines (HeLa, MCF-7, A549) in vitro, and the structure–activity relationships were summarized. The compound E43 exhibited the best inhibitory activity against HeLa, MCF-7, A549, displaying IC50 values of 1.48 ± 0.13, 3.01 ± 0.09, and 5.11 ± 0.13 μM. Molecular docking indicated that compound E43 may bind to protein (PDB:6FEX) via hydrogen bond and π stacking. Further, molecular dynamics simulations indicated a relatively low binding free energy (−40.06 kJ·mol−1) of compound E43 with protein. In conclusion, these findings suggested that E43 is promising as a potential novel anticancer drug candidate worthy of further investigation.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"1966-1979"},"PeriodicalIF":2.0,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142859896","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}

引用次数: 0