Journal of Heterocyclic Chemistry最新文献

{"title":"Synthesis of 2-aminothiazoles containing 3-hydroxypyran-4-one fragment based on condensation of substituted α-arylaminoketones with thiourea","authors":"Andrey N. Komogortsev,&nbsp;Valeriya G. Melekhina,&nbsp;Constantine V. Milyutin,&nbsp;Boris V. Lichitsky","doi":"10.1002/jhet.4876","DOIUrl":"10.1002/jhet.4876","url":null,"abstract":"<p>Condensation of α-arylaminoketones bearing 3-hydroxypyran-4-one fragment with thiourea was studied. Based on considered investigation, the method for the synthesis of terarylenes with 2-aminothiazole bridge was elaborated. The presented process is the first example of construction of thiazole core starting from α-aminoketone precursor. The advantages of developed approach are easily available starting materials and convenient isolation of target products avoiding chromatographic purification. The structure of one of prepared products was confirmed by x-ray analysis. The synthetic utility of obtained 2-aminothiazoles with allomaltol substituent was demonstrated by reaction at amino and hydroxyl groups.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1531-1541"},"PeriodicalIF":2.0,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141740494","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}

{"title":"Efficient synthetic strategies for fused pyrimidine and pyridine derivatives: A review","authors":"Sharmil N. Anjirwala,&nbsp;Saurabh K. Patel","doi":"10.1002/jhet.4871","DOIUrl":"10.1002/jhet.4871","url":null,"abstract":"<p>Pyrimidine and its derivatives play a paramount role in drug discovery as privileged pharmacophores with considerable chemical and biological significance and its presence in genes. This review aims to assemble a systematic evaluation of synthetic tactics of various fused pyrimidine derivatives containing nitrogen heterocycles such as pyridopyridines, pyridopyrimidines, and pyrimidopyrimidine from a pharmacological point of view and deliver an overview of methodologies presenting the chemistry of fused pyrimidine derivatives. The review details the importance of various catalysts and ring substitution using various electrophilic and nucleophilic reagents. These synthetic strategies were elaborated based on the different synthetic routes that lead to the specific type of pyrimidine and pyridine fused derivatives. The literature accumulates various developments in one-pot condensation, the Knoevenagel–Michael addition mechanism, microwave and ultrasound irradiation, intramolecular cyclization, nano-catalytic reactions, and so forth. Short reaction times, catalyst reusability, solvent-free conditions, excellent yields, and stereo-selectivity are some of the benefits of certain synthetic approaches.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1481-1516"},"PeriodicalIF":2.0,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141740496","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}

{"title":"DABCO-catalyzed highly regioselective synthesis of novel 4H-pyrano[2,3-b]quinoline derivatives: One-pot three-component reaction","authors":"Masumeh Heydari,&nbsp;Ali A. Mohammadi,&nbsp;Mohammad R. Mosleh","doi":"10.1002/jhet.4862","DOIUrl":"10.1002/jhet.4862","url":null,"abstract":"<p>A regioselective synthesis of 4<i>H</i>-pyrano[2,3-b]quinoline derivatives via DABCO-mediated Knoevenagel condensation/heterocyclization sequence has been executed. In this way some new fused heterocyclic compounds were synthesized from 2-chloroquinoline-3-carbaldehyde as a versatile and efficient synthetic building block. The one-pot three-component reaction of 2-chloroquinoline-3-carbaldehyde and diverse cyclic active methylenes for construction of highly substituted quinolines scaffold has been accomplished under mild condition. The strategy included herein shows significant advantages, including a facile process with easy purification, excellent yields, wide applicability, available substrates, and cost-effective/eco-friendly solvent and catalyst.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1446-1454"},"PeriodicalIF":2.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141585828","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}

{"title":"Synthesis of 6-R-N-aryl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amines based on N-(2,2,2-trichloro-1-(3-R-thioureido)ethyl)carboxamides: Their spectral characteristics and molecular structure","authors":"Yelyzaveta R. Lomynoha,&nbsp;Pavlo V. Zadorozhnii,&nbsp;Vadym V. Kiselev,&nbsp;Aleksandr V. Kharchenko","doi":"10.1002/jhet.4870","DOIUrl":"10.1002/jhet.4870","url":null,"abstract":"<p>In this work, we report the synthesis of a series of new 4<i>H</i>-1,3,5-oxadiazine derivatives. The method of their production is based on the dehydrosulfurization reaction of <i>N</i>-(2,2,2-trichloro-1-(3-<i>R</i>-thioureido)ethyl)carboxamides under the action of a mixture of iodine and triethylamine in DMF. A possible reaction mechanism has been proposed. The target products have been obtained in 58%–75% yield. The structure of the obtained compounds has been confirmed by ¹H, ¹³C NMR, IR spectroscopy data, and x-ray diffraction analysis carried out for 6-(<i>tert</i>-butyl)-<i>N</i>-phenyl-4-(trichloromethyl)-4<i>H</i>-1,3,5-oxadiazin-2-amine.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1467-1480"},"PeriodicalIF":2.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141611572","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}

{"title":"Rose bengal photocatalyzed expeditious multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under visible light irradiation","authors":"Divyani P. Patel,&nbsp;Vishwa K. Patel,&nbsp;Satish Kumar Singh","doi":"10.1002/jhet.4868","DOIUrl":"10.1002/jhet.4868","url":null,"abstract":"<p>The combination of visible light, a renewable and green energy source, and rose bengal, a non-toxic organic dye as a photoredox catalyst, is an easy and efficient method for synthesizing 3,4-dihydropyrimidin-2(1<i>H</i>)-ones/thiones in EtOH at ambient temperature in very short reaction time. The present work offers simple operation, easy workup, rapid conversion, and excellent product yields, while accommodating a wide range of substrates. Rose bengal-based photocatalytic approach permits foremost sustainability, which delivers economic and environmental rewards.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1455-1461"},"PeriodicalIF":2.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141585778","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}

{"title":"Structure–activity relationship investigations probing the cytotoxicity of 9-aminoacridine derivatives with PC3 and A549","authors":"Grace S. Blount,&nbsp;Austin Seymour,&nbsp;Dylan Williams,&nbsp;Daylon Douglas,&nbsp;Joshua Miller,&nbsp;Sarah Sejoro,&nbsp;Karl E. Peace,&nbsp;Jannet Kocerha,&nbsp;Karelle S. Aiken","doi":"10.1002/jhet.4869","DOIUrl":"10.1002/jhet.4869","url":null,"abstract":"<p>9-Aminoacridine structures hold much potential for accessing small molecule therapeutics. This core is present in a range of pharmaceuticals for the treatment of ailments such as malaria, inflammation, viral and bacterial infections, and cancer. For the latter, there remains a need to develop and/or improve chemotherapeutics to counteract issues of uptake, drug resistance, and selectivity for cancer cells over healthy cells. In the design of molecules to address these issues, identifying structural units that present as promising leads for drug development is key. In this study, four 9-aminoacridine derivatives under consideration as precursors for a drug design project are assessed for their cytotoxicity with representative cell lines PC3 and A549 and for their leadlikeness with SwissADME. Together, the cytotoxicity and in silico investigations coalesce around the same derivative as the most promising lead.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1439-1445"},"PeriodicalIF":2.0,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141585827","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}

{"title":"Synthesis and histone deacetylases inhibitory activity of pyrimidine-based 1,3,4-oxadiazoles","authors":"V. Jakubkiene,&nbsp;I. Labalaukyte,&nbsp;M. Schweipert,&nbsp;A. Zubriene,&nbsp;F.-J. Meyer-Almes,&nbsp;D. Matulis,&nbsp;S. Tumkevicius","doi":"10.1002/jhet.4867","DOIUrl":"10.1002/jhet.4867","url":null,"abstract":"<p>The histone deacetylases (HDACs) are being explored as a promising therapeutic target for the treatment of various diseases. Here, the synthesis of a series of pyrimidine-based 1,3,4-oxadiazoles, in which the oxadiazole scaffold is attached to the pyrimidine ring via a methyleneoxy spacer, is described and their HDAC inhibitory activity studied. The target compounds were synthesized by sequence of reactions involving <i>O</i>-alkylation of 2-(methylthio)pyrimidin-4(3<i>H</i>)-ones with ethyl 2-bromoethanoate followed by oxidation of the 2-methylthio group, displacement of the obtained 2-methylsulfonyl group with amines, hydrazinolysis of the obtained ethyl (2-amino-substituted pyrimidin-4-yloxy)acetates to give the corresponding hydrazides and their cyclization under the treatment with ethyl <i>O</i>-ethyl xanthate or carbonyldiimidazole to 1,3,4-oxadiazole-2(3<i>H</i>)-thiones and 1,3,4-oxadiazol-2(3<i>H</i>)-one, correspondingly. In addition, two 1,3,4-oxadiazole-2(3<i>H</i>)-thiones were converted into (<i>N</i>3)-morpholinomethyl derivatives by the Mannich reaction with formaldehyde and morpholine. The yields of intermediates and target compounds ranged from moderate to excellent. The synthesized compounds were characterized by ¹H and ¹³C NMR spectra and HRMS data, their purity was controlled by TLC. The synthesized pyrimidine-based 1,3,4-oxadiazoles (18 compounds) were tested as inhibitors of the HDAC4 and HDAC8 isoforms and their inhibitory activity was compared with that of Vorinostat. Most of the oxadiazolethiones containing methyl group at the position 6 of the pyrimidine moiety were found to be more selective towards HDAC8, while oxadiazolethiones with propyl group in the pyrimidine ring were active against HDAC4. Among the tested compounds, 5-((2-(dibutylamino)-6-propylpyrimidin-4-yloxy)methyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thione (<b>48</b>) was found to have the strongest inhibitory activity for HDAC4 isoform (IC₅₀ = 4.2 μM vs. IC₅₀ = 59 μM for Vorinostat) while 5-((2-(cyclopentylamino)-6-propylpyrimidin-4-yloxy)methyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thione (<b>50</b>) was the most potent HDAC8 inhibitor (IC₅₀ = 6.8 μM).</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1426-1438"},"PeriodicalIF":2.0,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141585779","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}

{"title":"Highly twisted 1,3,4-oxadiazole based hybrid fluorescent organic materials: Synthesis, characterization, density functional theory calculations, and optoelectronic study","authors":"Heena,&nbsp;Deepak Sharma,&nbsp;Hari Om,&nbsp;Ravi Rana","doi":"10.1002/jhet.4865","DOIUrl":"10.1002/jhet.4865","url":null,"abstract":"<p>Heterocyclic compounds based on 1,3,4-oxadiazole (ODA) have attracted considerable attention in the field of pharmacy, drug discovery, and in the field of material sciences. This article reports a series of new highly twisted blue- and green-emitting ODA-based materials <b>4</b>(<b>a</b>–<b>e</b>) utilizing a simple and efficient synthetic approach, resulting in high yield. The formation of multiple C<span></span>N bonds unfolds via a simple nucleophilic method that does not need costly metal catalysts. The derivative structures were validated using analytical methods such as ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry (HRMS). Using fluorescence spectroscopy, UV–Vis spectroscopy, and fluorescence lifetime measurements, a thorough investigation was carried out on the photophysical characteristics of the newly synthesized derivatives. A deeper understanding of intramolecular charge transfer was uncovered via solvent-dependent spectroscopy. Specifically, these materials show a large stock shift of up to 153 nm and long fluorescence decay value between 8 and 8.6 ns. Computational methods pinned on density functional theory (DFT) were used to determine the highest occupied molecular orbital–lowest unoccupied molecular orbital energy gaps. The optical band gaps derived from absorption peaks and the band gaps computed by DFT computations are highly correlated. Using cyclic voltammetry study, the compounds' redox potentials were further investigated. These results indicate that the ODAs <b>4</b>(<b>a</b>–<b>e</b>) are promising organic materials and could play an important role in the field of optoelectronic devices, bioimaging, and photo-redox reactions.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1417-1425"},"PeriodicalIF":2.0,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141550504","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}

{"title":"Studies on Isocyanides and Related Compounds. Synthesis of 3‐Substituted 2‐Arylsulfonylamino‐3,4‐dihydro‐4‐oxoquinazolines via a Novel Three‐Component Reaction","authors":"Ricardo Bossio, Stefano Marcaccini, Roberto Pepino","doi":"10.1002/j.1943-5193.1995.tb00001.x","DOIUrl":"https://doi.org/10.1002/j.1943-5193.1995.tb00001.x","url":null,"abstract":"The reaction between isocyanides 1,methyl anthranilate (2) and chloramines T (3a) or chloramines B (3b) occurred easily, in the presence of benzyltriethylammonium chloride to give the guanidines 4 which, upon heating, underwent a ring‐closure reaction to afford the title compounds 5.","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141505453","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}

{"title":"A highly effective method for the environmentally friendly production of novel chromene derivatives using electron deficient compounds","authors":"Faezeh Shafaei,&nbsp;Fariba Zamani Hargalani,&nbsp;Maryam Ghazvini","doi":"10.1002/jhet.4864","DOIUrl":"10.1002/jhet.4864","url":null,"abstract":"<p>New, high-yield derivatives of oxepino[3,2-c]chromene were synthesized through a multicomponent reaction. This reaction involved 2-hydroxyacetophenone, dimethyl carbonate, activated acetylenic compounds, and alkyl bromide. The reaction took place at room temperature in an aqueous environment, resulting in the formation of these innovative compounds. Oxathiepines were synthesized using multicomponent reactions of 2-hydroxyacetophenone, dimethyl carbonate, isothiocyanate, and alkyl bromide in water at room temperature. This technology offers several benefits, including quick response times, high product yields, and easy product separation using straightforward techniques.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1405-1410"},"PeriodicalIF":2.0,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141505454","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}