Hendawy N. Tawfeek, Tamer H. A. Hasanin, Stefan Bräse
{"title":"Synthetic methodology of pyrimido[4,5-b]quinoline derivatives","authors":"Hendawy N. Tawfeek, Tamer H. A. Hasanin, Stefan Bräse","doi":"10.1002/jhet.4815","DOIUrl":"10.1002/jhet.4815","url":null,"abstract":"<p>This review discusses the synthetic pathways of an important class of quinolines known as pyrimido[4,5-b]quinoline. Due to their profound range as biologically active compounds, they attracted the attention of medical/organic researchers. The construction of pyrimido[4,5-b]quinolines involved the intermolecular cyclization of diamino chloropyrimidine carbaldehyde and intramolecular cyclization of 2-amino-3-cyanotetra/hexahydroquinoline, 2-aminoquinoline-3-carbonitriles, ester or amide. That class of organic compounds was constructed from the reaction between 2-chloro-3-formylquinoline with amidine, urea, and thiourea. Also, barbituric acid and uracil and their analogous play an important role in synthesizing pyrimidoquinolines via multicomponent reaction strategies (MCR).</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"971-1008"},"PeriodicalIF":2.4,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140592086","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 anticancer activity of cinnoline sulphonamides and 4-heteroyclic derivatives: Cross-coupling approach","authors":"Jayaprakash Rao Yerrabelly, Mohan Babu Bommagani, Hemasri Yerrabelly, Sai Charitha Mullaguri, Rama Krishna Kancha","doi":"10.1002/jhet.4816","DOIUrl":"10.1002/jhet.4816","url":null,"abstract":"<p>A series of novel cinnoline sulphonamide derivatives and 4-substuted cinnoline derivatives (<b>13a-h</b>, <b>16a-h</b> and <b>17–31</b> total <b>33</b> analogues) were designed based on scaffold hopping techniques and evaluated for their antileukemic activity on wild type K562 as well as imatinib resistant cell lines (K562-IR1 and K562-IR2). Out of 33 analogues, five compounds (<b>19</b>, <b>22</b>, <b>23</b>, <b>28</b>, and <b>31</b>) exhibited potent antileukemic activity. An easy and efficient approach to synthesize numerous cinnoline derivatives by the various cross-coupling reactions of 4-chlorocinnoline has been developed and also demonstrated that metal-free cross couplings give high product yield compared with metal catalyzed cross couplings.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"958-970"},"PeriodicalIF":2.4,"publicationDate":"2024-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140358202","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":"Practical synthesis of (S)-pyroglutamic acid","authors":"Fernando Alves Barretto, Silvio Cunha","doi":"10.1002/jhet.4813","DOIUrl":"10.1002/jhet.4813","url":null,"abstract":"<p>A simple and rapid synthesis of (S)-pyroglutamic acid was developed by the thermal cyclodehydration of (S)-glutamic acid under solvent-free conditions, with continuous swirling during heating (220°C) to ensure homogeneity of the melt. The reaction proceeds until the bubbles disappear, not exceeding 5 min. The heating immediately ceases, then cooling the reaction vessel to prevent degradation and racemization. (S)-pyroglutamic acid is obtained in 70% yield, and the enantiomeric ratio is 97:3. The same reaction under microwave heating in an aqueous solution afforded a low yield of racemic product.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"955-957"},"PeriodicalIF":2.4,"publicationDate":"2024-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140325746","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}
Zongbo Xie, Xuehua Chen, Guofang Jiang, Qianwen Fan, Hong Yang, Zhanggao Le
{"title":"Photocatalytic synthesis of 2,4-substituted quinazolines via a one-pot, three-component reaction under catalyst-free conditions","authors":"Zongbo Xie, Xuehua Chen, Guofang Jiang, Qianwen Fan, Hong Yang, Zhanggao Le","doi":"10.1002/jhet.4810","DOIUrl":"10.1002/jhet.4810","url":null,"abstract":"<p>A novel, catalyst-free photoinduced synthesis of 2,4-substituted quinazoline using 2-amino-aryl ketone, an aldehyde, and ammonium acetate was developed. A series of 2,4-substituted quinazoline compounds were obtained via irradiating the reactants with a light-emitting diode light (18 W) at room temperature. The broad substrate range and excellent gram-scale experimental results demonstrate the versatility of the reaction. To the best of our knowledge, the synthesis of 2,4-substituted quinazoline using ammonium acetate as the nitrogen source under photocatalysis has not been reported thus far. This method utilizes visible light oxidation to eliminate the use of oxidants in the reaction and is complementary to previous methods.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"948-954"},"PeriodicalIF":2.4,"publicationDate":"2024-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140324484","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}
Viktorija Savickienė, Aurimas Bieliauskas, Sergey Belyakov, Algirdas Šačkus, Eglė Arbačiauskienė
{"title":"Synthesis and characterization of novel biheterocyclic compounds from 3-alkoxy-1H-pyrazole-4-carbaldehydes via multicomponent reactions","authors":"Viktorija Savickienė, Aurimas Bieliauskas, Sergey Belyakov, Algirdas Šačkus, Eglė Arbačiauskienė","doi":"10.1002/jhet.4804","DOIUrl":"10.1002/jhet.4804","url":null,"abstract":"<p>Several series of novel biheterocyclic compounds have been synthesized starting from 3-alkoxy-1<i>H</i>-pyrazole-4-carbaldehydes and employing different types of multicomponent reactions. The structures of the obtained 4-(pyrazol-4-yl)pyrano[2,3-<i>c</i>]pyrazole, 4-(pyrazol-4-yl)pyrazolo[4′,3′:5,6]pyrano[2,3-<i>b</i>]quinoline, 4-(pyrazol-4-yl)pyridine, and 4-[(pyrazol-4-yl)methylidene]-1,2-oxazole derivatives were thoroughly characterized and confirmed using detailed nuclear magnetic resonance spectroscopy (NMR), high-resolution mass spectrometry (HRMS), infrared spectroscopy (IR), and X-ray analysis.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"927-947"},"PeriodicalIF":2.4,"publicationDate":"2024-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140315402","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":"Iron-catalyzed intermolecular and intramolecular cyclization reactions of N-heterocycles","authors":"Jyoti Kaushik, Sonika Jain, Dharma Kishore, Jaya Dwivedi","doi":"10.1002/jhet.4812","DOIUrl":"10.1002/jhet.4812","url":null,"abstract":"<p>N-Heterocyclic compounds have been appealing pharmacophores in their use as drug production substrates. In this review paper, the cyclization of N-heterocycles, using iron as a catalyst, and their mechanistic pathways have been highlighted and presented comprehensively. This paper will provide researchers with in-depth knowledge of their approach to synthesis by employing a greener way rather than a conventional one. The present review firmly establishes that iron catalysts by their innate ability and inherent potential to acquire the four oxidation states coupled with their easy accessibility, inexpensive, and environment-friendly nature have remained the mainstay in chemistry as the evergreen catalyst in the domain of organic synthesis. This review paper extensively explores iron-catalyzed cyclization of N-heterocycles, elucidating mechanistic pathways and emphasizing greener synthesis methods. Iron's versatility, accessibility, and eco-friendliness solidify its position as a cornerstone in organic synthesis.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"875-910"},"PeriodicalIF":2.4,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140315245","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}
Fathi B. Nour Eldeen, Sayed A. S. Mousa, Ismail M. M. Othman, Mohamed I. H. El-Qaliei
{"title":"Design, synthesis, antimicrobial evaluation, molecular docking studies, and in silico prediction of ADME properties for novel pyrazolo[1,5-a]pyrimidine and its fused derivatives","authors":"Fathi B. Nour Eldeen, Sayed A. S. Mousa, Ismail M. M. Othman, Mohamed I. H. El-Qaliei","doi":"10.1002/jhet.4814","DOIUrl":"10.1002/jhet.4814","url":null,"abstract":"<p>Dienamine <b>2</b> was synthesized by reacting 5-aminopyrazole <b>1</b> with two moles of (DMF DMA). Enamine <b>2</b> underwent subsequent reactions with various reagents in different reaction media, leading to the formation of distinct compounds. In an acidic environment, enamine <b>2</b> reacted with acetyl acetone, benzoyl acetone, dimedone, and ethyl acetoacetate, resulting in the synthesis of compounds <b>9a</b>, <b>9b</b>, <b>13</b>, and <b>17</b>, respectively. Conversely, in a basic medium, dienamine <b>2</b> combined with malononitrile, ethyl cyanoacetate, and malononitrile dimer, yielding compounds <b>21a</b>, <b>21b</b>, and <b>25</b>. Moreover, by reacting with ammonium acetate in acetic acid, dienamine <b>2</b> produced compounds <b>28</b>. The synthesized compounds underwent in vitro testing against various bacterial and fungal strains, revealing significant antibacterial activity against hazardous bacterial strains. To identify potential bacterial targets, an in-silico study was initiated. Molecular docking investigations indicated that compound <b>25</b> exhibited the highest binding affinity toward dihydrofolate reductase and penicillin-binding proteins. Furthermore, compound <b>25</b> demonstrated robust physiochemical properties, bioavailability, and drug-like characteristics. These results collectively suggest the potential of compound <b>25</b> as a promising antibacterial agent with favorable drug properties.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"911-926"},"PeriodicalIF":2.4,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140315344","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}
Sidney Gustavo Diniz Feitosa, Ilária Martina Silva Lins, Larissa Gonçalves Maciel, Janaína Versiani dos Anjos
{"title":"Discovery of novel heterocyclic derivatives containing oxadiazolone or pyrimidinone cores as DPP-4 inhibitors","authors":"Sidney Gustavo Diniz Feitosa, Ilária Martina Silva Lins, Larissa Gonçalves Maciel, Janaína Versiani dos Anjos","doi":"10.1002/jhet.4811","DOIUrl":"10.1002/jhet.4811","url":null,"abstract":"<p>Type 2 diabetes is a chronic disease characterized by insulin resistance and alterations in incretin secretion, such as the glucagon-like peptide-1 (GLP-1) hormone. GLP-1 plays a crucial role in signaling insulin production in the pancreas, with its activity regulated by the dipeptidyl peptidase 4 (DPP-4) enzyme. DPP-4 presents an intriguing strategy for controlling type 2 diabetes. This study focuses on synthesizing 22 novel oxadiazolone and pyrimidinone derivatives, in vitro DPP-4 inhibition, and elucidating binding modes through molecular docking simulations. Nine compounds showed promising inhibitory activity, with IC<sub>50</sub> values ranging from 0.3 to 1.86 mM. Molecular docking simulations revealed interactions between these compounds and critical residues in the enzyme's active site, such as Arg125, Glu206, Ser630, and His740. This investigation introduces a new class of DPP-4 inhibitors, providing insights into the design of more potent molecules as potential candidates for combating type 2 diabetes. The findings contribute to developing innovative therapeutics for managing this prevalent metabolic disorder.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"861-874"},"PeriodicalIF":2.4,"publicationDate":"2024-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140203651","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, characterization, and antibacterial activity studies of β-lactam capped silver nanoparticles","authors":"Aarti Thakur, Suvidha Pandey, Mona Mittal, Renu Thapar","doi":"10.1002/jhet.4805","DOIUrl":"10.1002/jhet.4805","url":null,"abstract":"<p>A highly efficient, novel, two-phase liquid method using phase transfer catalyst is reported to prepare β-lactam-conjugated silver nanoparticles as an approach to improve antibacterial activity of β-lactams. In the method assisted by cetyltrimethylammonium bromide, NaBH<sub>4</sub> reduced AgNO<sub>3</sub> producing silver NPs that are coated with β-lactams. The studies conducted provide a generalized method applicable to all types of β-lactam substrates for capping on silver NPs. The NPs have been characterized by UV–Visible, Fourier transform infrared spectroscopy, x-ray diffraction, transmission electron microscopy, and dynamic light scattering methods.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"852-860"},"PeriodicalIF":2.4,"publicationDate":"2024-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140203929","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}
Lukas Bauer, Simon M. J. Endraß, Thomas M. Klapötke, Jörg Stierstorfer, Nicole Zeitlmeir
{"title":"N-Azidoethyl azoles through N-alkylation under highly harmonized reaction conditions: Synthesis, characterization, and complexation as energetic coordination compounds","authors":"Lukas Bauer, Simon M. J. Endraß, Thomas M. Klapötke, Jörg Stierstorfer, Nicole Zeitlmeir","doi":"10.1002/jhet.4803","DOIUrl":"10.1002/jhet.4803","url":null,"abstract":"<p>Organic azides are universally important in many areas of chemistry, particularly in organic synthesis. The availability of these azides often depends on specific transfer reagents and reaction conditions, or only work with certain substrates. Customizable transfer reagents offer a safe and direct pathway to desired compounds, thereby increasing the availability of <i>N</i>-alkyl-azides. In an effort to streamline the synthesis and broaden the scope of <i>N</i>-azidoethyl-containing molecules, three different versatile azidoethyl transfer reagents were synthesized and a uniform reaction protocol with azoles as substrates, including imidazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, and tetrazole was established. The resulting azidoethyl-azoles were further used as ligands for energetic coordination compounds in an effort to create new lead-free primary explosives. A comprehensive characterization of the transfer reagents, the azidoethyl-containing products, and energetic coordination compounds was conducted using multinuclear nuclear magnetic resonance (NMR), elemental analysis, mass spectrometry, and infrared spectroscopy (IR). Furthermore, their thermal stability and sensitivity toward friction and impact were determined as well as the detonation properties were calculated by using the EXPLO5 code.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"839-851"},"PeriodicalIF":2.4,"publicationDate":"2024-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.4803","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140203656","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}