Journal of Heterocyclic Chemistry最新文献

Cu(OTf)2 Catalyzed the Reaction of Donor-Acceptor Cyclopropanes With Salicylaldehyde Phenylhydrazones: Synthesis Polycyclic Tetrahydropyridazines Cu(OTf)2催化供体-受体环丙烷与水杨醛苯基腙的反应：合成多环四氢吡啶

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-05-23 DOI: 10.1002/jhet.4952

Zhiping Liu, Lijie Che, Jie Pang, Junan Xiao, Xiyan Tang, Chunfang Gan, Jianguo Cui, Yanmin Huang

引用次数: 0

Synthesis of Some Acyclonucleosides Analogs of 1,4-Benzothiazine and Their Sulfonates Derivatives: Crystal Structure, Spectroscopic Characterization, DFT Calculations, Hirshfeld Surface Analysis, and Molecular Docking With Mycobacterium tuberculosis 1,4-苯并噻嗪及其磺酸盐衍生物的一些环核苷类似物的合成：晶体结构、光谱表征、DFT计算、Hirshfeld表面分析以及与结核分枝杆菌的分子对接

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-05-13 DOI: 10.1002/jhet.4951

Ezaddine Irrou, Younesse Ait Elmachkouri, Yusuf Sert, Olivier Blacque, Joel T. Mague, Ouachtak Hassan, El Ghayati Lhoussaine, El Mokhtar Essassi, Nada Kheira Sebbar, Mohamed Labd Taha

{"title":"Synthesis of Some Acyclonucleosides Analogs of 1,4-Benzothiazine and Their Sulfonates Derivatives: Crystal Structure, Spectroscopic Characterization, DFT Calculations, Hirshfeld Surface Analysis, and Molecular Docking With Mycobacterium tuberculosis","authors":"Ezaddine Irrou, Younesse Ait Elmachkouri, Yusuf Sert, Olivier Blacque, Joel T. Mague, Ouachtak Hassan, El Ghayati Lhoussaine, El Mokhtar Essassi, Nada Kheira Sebbar, Mohamed Labd Taha","doi":"10.1002/jhet.4951","DOIUrl":"https://doi.org/10.1002/jhet.4951","url":null,"abstract":"<div>\u0000 \u0000 Ten acyclonucleoside analogs of 1,4-benzothiazine and their sulfone derivatives (3a,b–8a,b) were synthesized using alkylation reactions under phase-transfer catalysis (PTC) conditions. The reactions were conducted under optimized conditions, with reaction times ranging from 1.5 to 2 h and yields varying between 70% and 76%. All the synthesized products were characterized using 1H and 13C-NMR spectroscopy. Additionally, the structures of compounds 4a, 6b, 7a, and 8b were confirmed through single-crystal X-ray diffraction analysis. Spectral data were also calculated using density functional theory (DFT) at the B3LYP/6–311++G(d,p) level and compared with experimental results to better understand the non-binding intermolecular interactions in the solid-state crystal packing. Two-dimensional (2D) and three-dimensional (3D) Hirshfeld surface analyses were performed to identify the closest atomic contacts in the studied molecules. The structures of compounds 4a, 6b, 7a, and 8b were optimized and evaluated for their HOMO and LUMO energies, along with their corresponding orbital representations. A strong correlation was observed between the experimental and calculated results. Finally, molecular docking studies of compounds 4a, 6b, 7a, and 8b were performed to investigate their binding patterns with inhibitory targets from the Protein Data Bank (PDB: 4P8K-A chain: DprE1: decaprenylphosphoryl-β-D-ribose-2′-epimerase) from \u0000 Mycobacterium tuberculosis\u0000 , using the AutoDock Vina program.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 5-6","pages":"383-401"},"PeriodicalIF":2.0,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144482187","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

Palladium-Catalyzed Three-Component Reaction of Enol Ethers, Salicylaldehyde, and Trimethyl Orthoformate: A Fast Synthesis of Tetrahydro-2H,5H-Pyrano[2,3-b]Chromenes 钯催化烯醇醚、水杨醛和原甲酸三甲酯的三组分反应：快速合成四氢- 2h， 5h -吡喃[2,3-b]铬

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-03-02 DOI: 10.1002/jhet.4949

Melina D. Cordova-Rodríguez, José A. Olivares-Castillo, Marcos Flores-Álamo, William H. García-Santos, Martín A. Iglesias-Arteaga

引用次数: 0

An Efficient Catalyst-Free Protocol for the Synthesis of Various CNContaining Heterocycles at Ambient Temperature 常温下合成多种含C - <s:1> - N -杂环化合物的高效无催化剂方案

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-01-29 DOI: 10.1002/jhet.4948

Qiuyun Huang, Xinmei Xie, Huijun Ren, Liu Yang, Qiangwen Fan, Haibo Zhu, Zongbo Xie, Zhanggao Le

引用次数: 0

Synthesis of Terminal Alkenylindolines via Rhodium-Catalyzed Direct CH Alkenylation With Alkenyl Borates 铑催化硼酸烯基直接C -羟基烯化合成末端烯酸啉

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-01-27 DOI: 10.1002/jhet.4939

Liang Wang, Xiaoyu He, Cheng Luo, Pengjie Li, Yina Mei, Cheng Gong, Yimeng Wang, Jin Zhang

引用次数: 0

Pesticidal Efficacy of Innovative Heterocyclic Tosyl Esters: Design, Synthesis, Biochemical Assessment, and DFT Calculation 新型杂环Tosyl酯的杀虫效果：设计、合成、生化评价和DFT计算

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-01-19 DOI: 10.1002/jhet.4947

Heba M. Metwally, Ehab Abdel-Latif, Mohamed E. Mostafa, Gehad E. Said

引用次数: 0

T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones t3p促进一系列新型3-芳基-2-苯基-2,3,5,6-四氢- 4h -1,3-噻嗪-4-酮的合成

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-01-09 DOI: 10.1002/jhet.4938

Lee J. Silverberg, Tapas Mal, Anthony Lagalante, Mark Olsen, Michael Fleming, Tracy Garcia, Aloura Gavalis, Kyanna Gonzalez, Casey Gregory, Laine Hackenberg, Madeline Lawler, Eddie Li, Evelyn Louca, Shaheem Mack, Kristen Perhonitch, Kelsey Shaffer, Carter Thompson, Sarah Tran, Evan Vidal, Ryan Vidal

{"title":"T3P-Promoted Synthesis of a Series of Novel 3-Aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones","authors":"Lee J. Silverberg, Tapas Mal, Anthony Lagalante, Mark Olsen, Michael Fleming, Tracy Garcia, Aloura Gavalis, Kyanna Gonzalez, Casey Gregory, Laine Hackenberg, Madeline Lawler, Eddie Li, Evelyn Louca, Shaheem Mack, Kristen Perhonitch, Kelsey Shaffer, Carter Thompson, Sarah Tran, Evan Vidal, Ryan Vidal","doi":"10.1002/jhet.4938","DOIUrl":"https://doi.org/10.1002/jhet.4938","url":null,"abstract":"A series of 12 novel 3-aryl-2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of C-phenyl-N-aryl imines with 3-mercaptopropionic acid. Both electron-withdrawing and electron-donating substituents were used. All substituents were successful, including p-nitro. Some reactions were run as 3-component reactions, forming the imine in situ. The reactions were operationally simple and gave yields as high as 79%. An example was also done where a p-nitro group was on both the C-aryl and the N-aryl. This provides ready access to N-aryl compounds in this family, which have been generally difficult to prepare.","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 4","pages":"338-344"},"PeriodicalIF":2.0,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.4938","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143770388","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}

引用次数: 0

Synthesis of BZR-Cotoxin IV Analog and Evaluation of Its Cytotoxic Properties BZR-Cotoxin IV类似物的合成及其细胞毒性评价

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-01-06 DOI: 10.1002/jhet.4942

Suleman Duengo, Ace Tatang Hidayat, Weny J. A. Musa, Rani Maharani

{"title":"Synthesis of BZR-Cotoxin IV Analog and Evaluation of Its Cytotoxic Properties","authors":"Suleman Duengo, Ace Tatang Hidayat, Weny J. A. Musa, Rani Maharani","doi":"10.1002/jhet.4942","DOIUrl":"https://doi.org/10.1002/jhet.4942","url":null,"abstract":"<div>\u0000 \u0000 Our research team has successfully synthesized BZR-cotoxin IV, despite encountering considerable difficulties stemming from its unique structural features. The molecule's ester bond is particularly susceptible to hydrolysis, which leads to instability during the synthesis process. Moreover, the tendency of its linear precursor to form diketopiperazine (DKP) adds another layer of complexity to the synthesis. To overcome these obstacles, we adopted a strategy centered on developing an analog compound. This approach was guided by structure–activity relationship (SAR) principles. The key modification involved substituting the hydroxy acid residue (Hiv) found in the original BZR-cotoxin IV with its corresponding amino acid, valine. This strategic alteration was intended to not only potentially improve the compound's characteristics but also to streamline the synthesis procedure. The synthesis of [Val]7-BZR-cotoxin IV was accomplished using a hybrid approach that combined solid-phase and solution-phase peptide synthesis techniques. The linear precursor of [Val]7-BZR-cotoxin IV was produced using Fmoc chemistry on CTC resin, with HATU/HOAt serving as the coupling reagent for amide bond formation. This process yielded a 9.25% pure product as a white powder. The cyclization step was performed using HATU in a dilute solution, which produced cyclic [Val]7-BZR-cotoxin IV with a yield of 12.9% as a white powder. Cytotoxicity test was conducted on both the linear and cyclic forms of [Val]7-BZR-cotoxin IV together with its natural BZR-cotoxin IV against HeLa cancer cells. The result showed moderate activity, with IC50 values of 297.60 μM for the linear precursor and 161.58 μM for the cyclic analog. Notably, the cyclic [Val]7-BZR-cotoxin IV demonstrated higher cytotoxic activity compared with its natural counterpart, BZR-cotoxin IV, which had an IC50 value of 214.01 μM.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 4","pages":"330-337"},"PeriodicalIF":2.0,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143770042","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

Regio Selective Synthesis of Pyrazole Derivatives of 5-Chloro-2-Methoxy Phenyl Hydrazide and Their Biological Evaluation 5-氯-2-甲氧基苯基肼吡唑衍生物的区域选择性合成及其生物学评价

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2025-01-05 DOI: 10.1002/jhet.4941

Abhay Bavishi, Hardev Vala, Sagar Swami, Shailesh Thakrar, Anamik Shah, Dhiman Sarkar

{"title":"Regio Selective Synthesis of Pyrazole Derivatives of 5-Chloro-2-Methoxy Phenyl Hydrazide and Their Biological Evaluation","authors":"Abhay Bavishi, Hardev Vala, Sagar Swami, Shailesh Thakrar, Anamik Shah, Dhiman Sarkar","doi":"10.1002/jhet.4941","DOIUrl":"https://doi.org/10.1002/jhet.4941","url":null,"abstract":"<div>\u0000 \u0000 Present study involves synthesis of derivatives of (5-chloro-2-methoxyphenyl) (5-alkyl-3-(substituted) (phenyl/alkyl)-1H-pyrazol-1-yl) methanones. Structural elucidation of the synthesized compounds was depicted by the data of 1H and 13C NMR, IR, and Mass spectral analysis. The newly synthesized compounds 1a–1d and 2a–2i were screened in vitro against \u0000 Mycobacterium tuberculosis\u0000 H37Ra using an established XRMA protocol. Among the screened compounds, 2d, 2f, and 2h showed good percent inhibition against the active stage of \u0000 M. tuberculosis\u0000 H37Ra 80.77, 55.70, and 79.54, respectively, at 30 μg/mL of inhibitor concentration. Further in secondary screening, compound 2d exhibited significant antitubercular activity on the active stage of \u0000 M. tuberculosis\u0000 H37Ra with IC50 of 0.208 μg/mL. The synthesized compounds were also screened for antibacterial activity and found no significant activity against Gram-positive Bacteria Bacillus subtitles and \u0000 Staphylococcus aureus\u0000 and Gram negative bacteria \u0000 Pseudomonas aeruginosa and Escherichia \u0000 coli\u0000 at 30 μg/mL, which confirms the specificity of inhibitory activity against \u0000 M. tuberculosis\u0000 and more selectively against the active stage. The present study will be helpful for the further development of these molecules into antitubercular lead candidates.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 4","pages":"325-329"},"PeriodicalIF":2.0,"publicationDate":"2025-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143770212","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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One-Pot Sequential Four-Component Reaction for the Synthesis of Novel Dihydro Oxaphospholo Pyrazole 2-Oxides in Acetic Acid Medium 醋酸介质中一锅顺序四组分反应合成新型二氢氧磷吡唑2-氧化物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-12-29 DOI: 10.1002/jhet.4946

Mingshu Wu, Zhengfan Sun, Rui Ning, Ziwen Yan, Junying Ma, Siqi Fan

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