Journal of Heterocyclic Chemistry最新文献_第3页

Aziridine-Functionalized 1,3,5-Triazine Derivatives as Promising Anticancer Agents: Synthesis, DFT Study, DNA Binding Investigations and In Vitro Cytotoxic Activity 氮丙啶官能化 1,3,5-三嗪衍生物作为有前途的抗癌剂：合成、DFT 研究、DNA 结合研究和体外细胞毒性活性

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-22 DOI: 10.1002/jhet.4908

Aleksandra V. Protas, Olga V. Mikolaichuk, Еlena А. Popova, Kirill V. Timoshchuk, Ilya V. Kornyakov, Dmitrii N. Maistrenko, Oleg E. Molchanov, Vladimir V. Sharoyko, Konstantin N. Semenov

引用次数: 0

Arylation of 2-Chloro-3-(4,6-Diaryl-1,3,5-Triazin-2-yl) Quinolines: Formal Synthesis of 3-(4,6-Diaryl-1,3,5-Triazin-2-yl)-2-Substituted Quinolines by Suzuki–Miyaura Reaction 2-氯-3-(4,6-二芳基-1,3,5-三嗪-2-基)喹啉的芳基化反应：通过铃木-宫浦反应正式合成 3-(4,6-二芳基-1,3,5-三嗪-2-基)-2-取代的喹啉类化合物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-20 DOI: 10.1002/jhet.4909

Joo-Hyun Jeon, Han-Joo Lee, Jin-Hee Kim, Mohammed B. Hawsawi, Hitesh B. Jalani, Jin-Hyun Jeong

引用次数: 0

Iodine-Promoted Cascade Redox Cyclization to Access 2-Arylbenzothiazoles Using Elemental Sulfur 利用元素硫进行碘促进级联氧化还原环化以获得 2-芳基苯并噻唑

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-20 DOI: 10.1002/jhet.4902

Yakkanti Chiranjeevi, Sujeet Gaware, Rana Chatterjee, Jayshree Solanke, Rapolu Venkateshwarlu, L. Vaikunta Rao, Gorle Simhachalam, Rambabu Dandela

引用次数: 0

Organocatalytic[3 + 2]Cycloaddition: Synthesis of Quinazoline Containing Sulfonyl 1,2,3-Triazoles as Potent EGFR Targeting Anti-Breast Cancer Agents 有机催化[3 + 2]环加成：合成含喹唑啉的磺酰基 1,2,3-三唑类 EGFR 靶向抗乳腺癌药物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-18 DOI: 10.1002/jhet.4905

Venkat Reddy Dodlapati, E. Ramya Sucharitha, Rambabu Palabindela, Ravikumar Kapavarapu, Sridhar Kavela, Sirassu Narsimha

{"title":"Organocatalytic[3 + 2]Cycloaddition: Synthesis of Quinazoline Containing Sulfonyl 1,2,3-Triazoles as Potent EGFR Targeting Anti-Breast Cancer Agents","authors":"Venkat Reddy Dodlapati, E. Ramya Sucharitha, Rambabu Palabindela, Ravikumar Kapavarapu, Sridhar Kavela, Sirassu Narsimha","doi":"10.1002/jhet.4905","DOIUrl":"10.1002/jhet.4905","url":null,"abstract":"<div>\u0000 \u0000 A general strategy was developed for the synthesis of new fully decorated 1,2,3-triazoles (4a–4m and 5a–5g) containing quinazolines from 1-(4-nitrophenyl)-2-(quinazolin-8-ylsulfonyl) ethan-1-one and several azides using Ramachary organocatalytic azide-ketone cycloaddition method. This reaction is reported for the synthesis of fully substituted sulfonyl-1,2,3-triazolyl quinazolins at a temperature of 100°C and the yields of the products produced are satisfactory to excellent. In vitro anticancer activity of all these derivatives demonstrated that six compounds, 4d, 4f, 4i, 4j, 5d, and 5e, were effective against two human breast cancer cell lines, MCF-7 and MDA-MB-231. Compounds 4f, 4j, and 5d had more action against both cell lines than Erlotinib. Later, the findings of inhibitory assays of potent compounds 4d, 4f, 4i, 4j, 5d, and 5e against the tyrosine kinase EGFR revealed that compound 5d proved more potent than the reference erlotinib, while 4f and 4j had comparable efficacy. In silico molecular docking studies were also performed on six strong medicines to identify interactions with the EGFR receptor, and the energy estimations were shown to be comparable with the observed IC50 values. Ultimately, using SWISS/ADME and pkCSM, the in silico pharmacokinetic profile of potent compounds 4d, 4f, 4i, 4j, 5d, and 5e was predicted. All of the compounds precisely followed the principles established by Lipinski, Veber, Egan, and Muegge.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1762-1776"},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264385","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

Efficient Synthesis and Comprehensive Characterization of bis-Pyrazole Derivatives: Including X-Ray Crystallography and Hirshfeld Surface Analysis 双吡唑衍生物的高效合成与综合表征：包括 X 射线晶体学和 Hirshfeld 表面分析

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-18 DOI: 10.1002/jhet.4906

Ahmed T. A. Boraei, Saied M. Soliman, Matti Haukka, Assem Barakat, Ahmed A. M. Sarhan

{"title":"Efficient Synthesis and Comprehensive Characterization of bis-Pyrazole Derivatives: Including X-Ray Crystallography and Hirshfeld Surface Analysis","authors":"Ahmed T. A. Boraei, Saied M. Soliman, Matti Haukka, Assem Barakat, Ahmed A. M. Sarhan","doi":"10.1002/jhet.4906","DOIUrl":"10.1002/jhet.4906","url":null,"abstract":"<div>\u0000 \u0000 Straightforward synthetic access to \u0000 bis\u0000 -pyrazole derivatives has presented. The titled \u0000 bis\u0000 -pyrazole derivative: 3′,5-diphenyl-1′,2-\u0000 bis\u0000 (5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-1′H,2H-[3,4′-\u0000 bis\u0000 pyrazol]-5′-ol 3 was obtained from the reaction of pyran-2,4-dione 1 and 4-hydrazineyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine 2 in ethanol in a one-step reaction. The other \u0000 bis-pyrazole derivative: 5,5′-diphenyl-1′H,2H-[3,4′-bispyrazol]-3′-ol 5 formed from hydrazinolysis of pyran-2,4-dione 1 or (E)-3-((allylamino)(phenyl)methylene)-6-phenyl-2H-pyran-2,4(3H)-dione 4 in ethanol. The molecular structure of both compounds elucidated by X-ray crystallographic identification and spectrophotometric tools. The supramolecular structure of 3 could be described as a hydrogen bonded dimer via O–H…N interactions which are further connected by π…π contacts. Hirshfeld analysis showed the significance of the N…H, O…H, C…H, C…C, N…N, C…O and H…H interactions. These contacts contributed by 14.4%, 3.2%, 16.4%, 3.9%, 1.0%, 0.4% and 42.7%, respectively from the whole interactions occurred in the crystal. The d\u0000 norm, shape index and curvedness maps revealed the importance of π–π stacking interactions in the molecular packing where the % C…C is 3.9%. In case of 5, the short N…H, C…H, and H…H contacts contributed by 15.5%–17.0%, 28.3%–36.7% and 37.8%–45%, respectively in the molecular packing.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1777-1788"},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264386","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

Discovery of Structural Diversity Guided N-S Heterocyclic Derivatives Based on Natural Benzothiazole Alkaloids as Potential Cytotoxic Agents 发现基于天然苯并噻唑生物碱的结构多样性引导的 N-S 杂环衍生物，作为潜在的细胞毒性药物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-16 DOI: 10.1002/jhet.4886

Lirong Guo, Yafei Wan, Manli Liu, Fuqiang Zheng, Yingwu Shi, Kaimei Wang, Xiufang Cao, Longzhu Bao, Shaoyong Ke

引用次数: 0

Multicomponent Assembling of Aldehydes, N,N-Dimethylbarbituric Acid, Malononitrile, and Morpholine Into Unsymmetrical Ionic Scaffold and Its Efficient Cyclization 醛、N,N-二甲基巴比妥酸、丙二腈和吗啉的多组分组装成不对称离子支架及其高效环化作用

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-16 DOI: 10.1002/jhet.4888

Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Mikhail P. Egorov

{"title":"Multicomponent Assembling of Aldehydes, N,N-Dimethylbarbituric Acid, Malononitrile, and Morpholine Into Unsymmetrical Ionic Scaffold and Its Efficient Cyclization","authors":"Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Mikhail P. Egorov","doi":"10.1002/jhet.4888","DOIUrl":"10.1002/jhet.4888","url":null,"abstract":"<div>\u0000 \u0000 The new type of the four-component tandem Knoevenagel–Michael reaction was discovered: the transformation of arylaldehydes, N,N′-dimethylbarbituric acid, malononitrile, and morpholine in alcohols and other organic solvents without any other additives at ambient temperature resulted in the selective formation of a new substituted unsymmetrical ionic scaffold with two pharmacology-active heterocyclic rings. This new four-component reaction is a simple and efficient route to a previously unknown substituted ionic unsymmetrical scaffold containing N,N′-dimethylbarbituric acid and morpholine. These ionic scaffolds are promising for various biomedical applications, for example, as anticonvulsants and anti-inflammatory drugs, as well as anti-AIDS agents. In this research, we also accomplished the efficient cyclization of morpholin-4-ium 5-(2,2-dicya-no-1-arylethyl)-1,3-dimethyl-2,6-di-oxo-1,2,3,6-tetrahydro-pyrimidin-4-olates by the action of NBS–NaOAc system, with the formation of 5,7-dimethyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1,1-dicarbonitriles in 83%–98% yields. In the final stage of our research, direct one-pot multicomponent transformation of benzaldehydes, N,N′-dimethylbarbituric acid, and malononitrile into spirobarbituric cyclopropanes was accomplished in 75%–97% yields. The spiro-barbituric cyclopropanes are potentially active as remedies against various inflammatory, infectious, immunological, or malignant diseases.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1752-1761"},"PeriodicalIF":2.0,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142264433","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

Mn(III)-Based Oxidation of (Methylene)Bis(Cyclodiamide)s. Facile Synthesis of Tetraazadispiro-(Undecanone)s and -(Tridecanone)s 基于锰(III)的(亚甲基)双(环二胺)氧化。四氮双螺-(十一烷酮)和-(十三烷酮)的简单合成

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-15 DOI: 10.1002/jhet.4891

Haruki Kamachi, Takumi Toki, Ayaka Nakamura, Hiroshi Nishino

引用次数: 0

Synthesis of Novel Nitroimidazole-Pyrazole Hybrids via an Attractive Methodology of N-Alkylation of 4(5)-Nitro-1H-imidazole 通过 4(5)-硝基-1H-咪唑 N-烷基化的诱人方法合成新型硝基咪唑-吡唑混合物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-12 DOI: 10.1002/jhet.4897

Rafaela Corrêa Silva, Maurício Silva dos Santos

引用次数: 0

Energetic Azoxy-Coupled Tetrazoles 高能偶氮偶联四唑