Journal of Heterocyclic Chemistry最新文献

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

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Synthesis and Anticancer Evaluation of Tryptanthrin-1,2,3-Triazole Hybrids 胰黄素-1,2,3-三唑杂化物的合成与抗癌评估

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-26 DOI: 10.1002/jhet.4916

C. B. Meenakshy, Sudheendran Leena Sruthi, E. G. Jayasree, Karakkadparambil Sankaran Sandhya, Ani Deepthi

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Syntheses of 2,4-Substituted Quinazolines via One-Pot Three-Component Reactions Based on Manganese Dioxide/tert-Butyl Hydrogen Peroxide Co-Oxidation Using Alcohols 基于二氧化锰/过氧化氢叔丁酯与醇的一锅三组分反应合成 2,4-取代的喹唑啉类化合物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-25 DOI: 10.1002/jhet.4913

Yihong Wang, Sheng Huang, Xuehua Chen, Haibo Zhu, Zhanggao Le, Zongbo Xie

{"title":"Syntheses of 2,4-Substituted Quinazolines via One-Pot Three-Component Reactions Based on Manganese Dioxide/tert-Butyl Hydrogen Peroxide Co-Oxidation Using Alcohols","authors":"Yihong Wang, Sheng Huang, Xuehua Chen, Haibo Zhu, Zhanggao Le, Zongbo Xie","doi":"10.1002/jhet.4913","DOIUrl":"https://doi.org/10.1002/jhet.4913","url":null,"abstract":"<div>\u0000 \u0000 Quinazolines and their derivatives occur in various natural products and pharmaceuticals, and thus, various methods of synthesizing quinazolines have been explored. They have traditionally been synthesized via two-component reactions, but these strategies often suffer from the unavailability of the starting materials and limited substrate scopes. To overcome these problems, three-component reactions using additional N sources were developed. Aldehydes were initially used in these reactions, but alcohols are greener and less toxic than aldehydes. However, the previously reported methods involving the use of alcohols require the utilization of transition metal catalysts, ultrahigh temperatures, and extended durations. Thus, an efficient, practical method of synthesizing quinazolines using alcohol is desirable. A facile one-pot three-component method of synthesizing quinazolines utilizing alcohols, 2-aminobenzoketones, and ammonium acetate is reported for the first time, using active MnO2 and tert-butyl hydrogen peroxide (TBHP) as synergistic oxidants. MnO2 and TBHP play dual roles: First, they oxidize the alcohol to the aldehyde and then facilitate the transformation of the intermediate into the product. During alcohol oxidation, the synergistic effect of MnO2 and TBHP is particularly evident. The aldehydes generated in situ via alcohol oxidation undergo immediate subsequent reactions, thereby minimizing their volatilization and side reactions, such as oxidation and polymerization.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1882-1890"},"PeriodicalIF":2.0,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642521","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, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5-Imino-7-Aryl-5 H-Thiazolo[3.2-a]Pyrimidine-6-Carbonitrile and Its Derivatives 新型 5-氨基-7-芳基-5 H-噻唑并[3.2-a]嘧啶-6-甲腈及其衍生物的合成、荧光特性、分子对接研究和晶体结构分析

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-25 DOI: 10.1002/jhet.4890

Yousseuf Touati, Mohammed Benabdallah, Ihcen Merabat, Julio A. Sejas, Ridha Hassaine, Ahmed Djafri, Abdelghani Bouchama, Abdelkader Chouaih, M. P. Vázquez-Tato, Noureddine Choukchou-Braham

{"title":"Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5-Imino-7-Aryl-5\u0000 H-Thiazolo[3.2-a]Pyrimidine-6-Carbonitrile and Its Derivatives","authors":"Yousseuf Touati, Mohammed Benabdallah, Ihcen Merabat, Julio A. Sejas, Ridha Hassaine, Ahmed Djafri, Abdelghani Bouchama, Abdelkader Chouaih, M. P. Vázquez-Tato, Noureddine Choukchou-Braham","doi":"10.1002/jhet.4890","DOIUrl":"https://doi.org/10.1002/jhet.4890","url":null,"abstract":"<div>\u0000 \u0000 This study describes a simple, inexpensive, and effective method for the synthesis of new 5-imino-7-aryle-5H-thiazolo[3,2-a]pyrimidine-3-carbonitrile derivatives 4a-e using a green procedure that does not require the use of heat or a base, creating a strategy that meets both economic and environmental demands. Various synthesized products were characterized via diverse techniques such as 1H-NMR, infrared (FT-IR), Mass spectroscopy (MS), and single crystal X-ray diffraction. Using a fluorescence spectrometer, the 5-imino-7-phenyle-5H-thiazolo[3.2-a]pyrimidine-3-carbonitrile 4a has been tested as a potent fluorescent agent in mixture of DMSO/Water at 10−4 M in one hand, and on the other hand the results of our fluorescence evaluation studies with metal ions (Pb(II), Ba(II), Cd(II), Ni(II), Mn(II), Hg(II), Zn(II), Fe(II), Co(II), Cu(II), La(II), Cr(III), and Fe(III)) have shown that this compound exhibits a turn-on and turn-off of the fluorescence to 4a compound with these metals, what forms poor to good interaction by these ions. This result represents the emergence of a new potential ligand for the two heavy cations Cd(II) and Pb(II), which are toxic and polluting, and whose detection is currently of high interest. As well, In the molecular docking evaluation study, it was determined that the 4e molecule has an exceptional ability to inhibit the binding energy of the tubulin protein by −9.13 kcal/mmol, compared to other compounds. The results demonstrate the possibilities for a novel oral medication application.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1870-1881"},"PeriodicalIF":2.0,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642522","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

Synthetic Approaches Toward Imidazo-Fused Heterocycles: A Comprehensive Review 咪唑杂环的合成方法：全面综述

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-24 DOI: 10.1002/jhet.4910

Pragati Kushwaha, Rashi, Ayush Bhardwaj, Danish Khan

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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

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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

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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

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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}

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