Journal of Heterocyclic Chemistry最新文献_第5页

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

引用次数: 0

Current Advances in Synthesis of Pyrazole Derivatives: An Approach Toward Energetic Materials 吡唑衍生物的合成研究进展：含能材料的研究方向

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 新型四氢恶唑[5′，4′：4,5]嘧啶[1,2-a]氮平酮衍生物抗癌药物的设计、合成及体外评价

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

The Study of Reaction of Hexafluoro-1,4-Napthoquinone With Substituted 5-Aminopyrazoles 六氟-1,4-萘醌与取代的5-氨基吡唑反应的研究

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-30 DOI: 10.1002/jhet.4911

Ekaterina N. Kudryavtseva, Boris V. Lichitsky, Andrey N. Komogortsev, Constantine V. Milyutin, Evgeny V. Tretyakov

{"title":"The Study of Reaction of Hexafluoro-1,4-Napthoquinone With Substituted 5-Aminopyrazoles","authors":"Ekaterina N. Kudryavtseva, Boris V. Lichitsky, Andrey N. Komogortsev, Constantine V. Milyutin, Evgeny V. Tretyakov","doi":"10.1002/jhet.4911","DOIUrl":"https://doi.org/10.1002/jhet.4911","url":null,"abstract":"<div>\u0000 \u0000 For the first time, the interaction of perfluoro-1,4-naphthoquinone with various 5-aminopyrazoles was investigated. It was shown that three types of products can be obtained depending on the structure of starting aminopyrazole. For all examples, the substitution of one fluorine atom in quinone moiety was observed. Wherein, in most cases, the starting aminopyrazoles act as a C-nucleophile leading to 2-(5-aminopyrazol-4-yl)-3,5,6,7,8-pentafluoronaphthalene-1,4-diones. At the same time substrates unsubstituted at ring nitrogen atom regiospecifically react at aminogroup resulting in the formation of 2,5,6,7,8-pentafluoro-3-((pyrazol-5-yl)amino)naphthalene-1,4-diones. Besides that, the absence of steric hindrance in the pyrazole unit allowed us to direct the process at nitrogen atom in Position 2 and synthesize zwitter-ionic 3-(5-aminopyrazol-2-ium-2-yl)-5,6,7,8-tetrafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-olates. The structures of two types of obtained products were confirmed by x-ray analysis.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"1932-1941"},"PeriodicalIF":2.0,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862414","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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GaCl3-Catalyzed [3 + 2]-Cycloaddition/Esterification Cascade of Donor–Acceptor Cyclopropanes With Salicylaldehydes for the Synthesis of Tetrahydro-4 H-Furo[3,2-c]Chromen-4-Ones gacl3催化[3 + 2]-环丙烷与水杨醛的环加成/酯化级联反应合成四氢-4 h -呋喃[3,2-c]铬-4-酮

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-30 DOI: 10.1002/jhet.4917

Zhiping Liu, Jie Pang, Lijie Che, Chunfang Gan, Jianguo Cui, Yanmin Huang

引用次数: 0

Practical Copper-Catalyzed Double N-Arylation of Cyclic Diaryliodoniums: Synthesis of 5H-Dibenzo[d, f][1,3]Diazepine, and Benzo[c]Cinnoline Derivatives 铜催化环二芳基鎓的双n -芳基化：5h -二苯并[d， f][1,3]二氮卓和苯并[c]喹啉衍生物的合成

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-30 DOI: 10.1002/jhet.4914

Lianji Zhang, Yujuan Wu, Yuhui Zhao, Cuiping Wang, Wanguo Wei, Zhiqiang Zhang

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A New Route for the Synthesis of (Trichloromethyl)Quinazoline-4(1H)-One and (1,2,3-Triazole)-Quinazoline-4(1H)-One Functionalized Derivatives via Copper-Catalyzed One-Pot Multicomponent Reactions 铜催化一锅多组分反应合成（三氯甲基）喹唑啉-4(1H)- 1和（1,2,3-三唑）-喹唑啉-4(1H)- 1功能化衍生物的新途径

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI: 10.1002/jhet.4899

Manijeh Nematpour

{"title":"A New Route for the Synthesis of (Trichloromethyl)Quinazoline-4(1H)-One and (1,2,3-Triazole)-Quinazoline-4(1H)-One Functionalized Derivatives via Copper-Catalyzed One-Pot Multicomponent Reactions","authors":"Manijeh Nematpour","doi":"10.1002/jhet.4899","DOIUrl":"https://doi.org/10.1002/jhet.4899","url":null,"abstract":"<div>\u0000 \u0000 The synthesis of functionalized (trichloromethyl)quinazoline-4(1H)-one with high yields through a novel three-component intramolecular CH activation reaction from trichloroacetonitrile, benzoyl chlorides, and various primary amines is a remarkable achievement in organic chemistry. This strategy offers a direct and efficient route to access complex molecular structures from readily available starting materials. The use of copper (I) as a catalyst and L-proline as a ligand in tetrahydrofuran at room temperature highlights the importance of transition metal catalysis in enabling selective CH activation processes. Furthermore, the subsequent transformation of the obtained product with phenylacetylene and sodium azide in the presence of a copper catalyst in water solvent at room temperature demonstrates the versatility of this synthetic approach in accessing new (1,2,3-triazole)-quinazoline-4(1H)-one derivative. The combination of available starting materials, catalytic systems, mild reaction conditions, and ease of purification procedures contributes to the attractiveness of this method for the synthesis of diverse (trichloromethyl)quinazoline-4(1H)-one and (1,2,3-triazole)-quinazoline-4(1H)-one derivative.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"1914-1923"},"PeriodicalIF":2.0,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862356","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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Palladium-Catalyzed Synthesis of Pyrrolo[1,2-α]Pyrazines From N-Phenacyl Pyrrole-2-Carbonitriles and Aryl Boronic Acids 钯催化 N-苯酰基吡咯-2-甲腈和芳基硼酸合成吡咯并[1,2-α]吡嗪类化合物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI: 10.1002/jhet.4898

Hyejun Park, Seunghwan Shim, Hayoung Jeon, Hwayoung Lee, Kiho Lee, Kyeong Lee, Jae Kyun Lee, Hitesh B. Jalani, Yongseok Choi

引用次数: 0

Benzenediazonium Tetrafluoroborate-Catalyzed Formal [3 + 3] Cyclization of 4-Hydroxycoumarins With Propargylicalcohols 四氟硼酸苯二氮鎓催化4-羟基香豆素与丙炔醇的正规[3 + 3]环化

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI: 10.1002/jhet.4912

Rongxiang Chen, Xingshuo Li, Jutuan Xiao, Mingli Zhu, Aili Sun, Kai-Kai Wang

引用次数: 0