Journal of Heterocyclic Chemistry最新文献

{"title":"Synthesis of Glycosides Containing d-Allose","authors":"Aoi Ikemoto,&nbsp;Diao Huanlin,&nbsp;Chou Chi,&nbsp;Suguru Murakami,&nbsp;Ryosuke Matsubara,&nbsp;Masahiko Hayashi","doi":"10.1002/jhet.70037","DOIUrl":"https://doi.org/10.1002/jhet.70037","url":null,"abstract":"<div>\u0000 \u0000 <p>Glycosides containing <span>d</span>-allose have been synthesized. Suitable glycosyl donors and promoters or additives are dependent on the nature of the aglycone. For (+)-catechin, using glycosyl fluorides as the glycosyl donor and BF₃ · OEt₂ as the promoter was the optimal choice. On the other hand, glycosyl bromide and tetrabutylammonium bromide (TBAB) or benzyltrietylammonium chloride (TEBAC) as the glycosyl donor and additive, respectively, proved to be the best combination for synthesizing glycosides containing <span>l</span>-ascorbic acid via Lemieux's halide ion-catalyzed glycosidation reaction.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"892-898"},"PeriodicalIF":2.0,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013099","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":"Electrochemically Enabled BTPPO-Mediated Halocyclization of Olefinic Amides","authors":"Zhenpu Wang,&nbsp;Wei Jin,&nbsp;Zixi Xie,&nbsp;Xinyu Liu,&nbsp;Fei Xue,&nbsp;Mengtao Ma,&nbsp;Weiwei Yao","doi":"10.1002/jhet.70040","DOIUrl":"https://doi.org/10.1002/jhet.70040","url":null,"abstract":"<div>\u0000 \u0000 <p>A simple and efficient electrochemical synthesis of 4-halomethyl benzoxazines via halocyclization of olefinic amides with ⁿBu₄NX as a halogen source has been reported for the first time. The crucial use of BTPPO as a mediator effectively mitigates the high oxidation potential of the substrate. The absolute structures of products were confirmed by single crystal X-ray diffraction characterization. The plausible reaction mechanism was investigated based on the corresponding radical trapping and CV experiments.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"899-905"},"PeriodicalIF":2.0,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013094","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":"Diastereoselectivity in the Synthesis of m- and p-Substituted 3-Aryl-2-trichloromethyl-1,3-thiazolidin-4-one Sulfoxides With Oxone","authors":"Ahmed Y. Nuriye,&nbsp;Kevin C. Cannon,&nbsp;Anna Sigmon,&nbsp;John Tierney","doi":"10.1002/jhet.70024","DOIUrl":"https://doi.org/10.1002/jhet.70024","url":null,"abstract":"<p>\u0000 <i>S</i>-Oxidation of 3-Aryl-2-trichloromethyl-1,3-thiazolidin-4-ones with Oxone was investigated. For all compounds evaluated, selective oxidation to the sulfoxide versus the sulfone was realized using 3 equivalents of Oxone at room temperature. The diastereoselectivity of sulfoxide formation always favored the <i>anti</i> product, but the extent of the selectivity varied according to the solvent used. Generally, higher selectivity was observed using acetone and acetonitrile, and lower selectivity was observed using methanol. Alternatively, sulfones were prepared by reaction with KMnO₄ at room temperature.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"880-891"},"PeriodicalIF":2.0,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.70024","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013098","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}

{"title":"Visible Light-Mediated Synthesis of Quinazoline and Quinazolinone Derivatives: A Quadrennial Update","authors":"Ravi Varala,&nbsp;Murali Mohan Achari Kamsali,&nbsp;Mohamed Hussein,&nbsp;Mohammed Mujahid Alam","doi":"10.1002/jhet.70013","DOIUrl":"https://doi.org/10.1002/jhet.70013","url":null,"abstract":"<div>\u0000 \u0000 <p>Quinazoline and quinazolinones are among the most significant nitrogenous heterocycles in medicinal chemistry, with a broad range of biological properties. There are several traditional methods to generate them in the literature. Most of them include the generation of enormous amounts of waste, laborious workup, and poor-yield products, all of which contribute to the impact on the environment. Therefore, it would be ideal to employ moderate, straightforward methods to construct such a strong nucleus. However, during the past fifteen years, visible light-mediated transformations have also garnered a lot of interest as an environmentally friendlier and greener alternative since they use photons as a clean energy source. This study investigates a range of representative synthetic protocols from 2021 forward to date, therefore expanding our understanding of visible light-driven quinazoline and quinazolinone derivative synthesis. It also generates ideas for potential future developments. This compendium is organized based on the type of heterocyclic scaffold that was synthesized. The scopes, limits, and mechanistic research of various study findings are also discussed.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"848-879"},"PeriodicalIF":2.0,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013307","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":"Cycloaddition or Metathesis: Selectivity in a Series of Indole-2,3-Quinodimethane Derivatives","authors":"Mikhail E. Kletskii,&nbsp;Konstantin F. Suzdalev,&nbsp;Anton V. Lisovin,&nbsp;Ekaterina A. Lysenko,&nbsp;Oleg N. Burov,&nbsp;Sergey V. Kurbatov","doi":"10.1002/jhet.70043","DOIUrl":"https://doi.org/10.1002/jhet.70043","url":null,"abstract":"<div>\u0000 \u0000 <p>The efficiency of combining experimental methods and quantum chemical calculations (DFT and ab initio) for optimizing conditions and predicting mechanisms for the interaction of acyclic and cyclic derivatives of indole-2,3-quinodimethane with heterodienophiles is demonstrated. For the reactions of acyclic derivatives of indole-2,3-quinodimethane with nitriles and carbon disulfide, indoles, [<i>b</i>]-fused with nitrogen- and sulfur-containing six-membered rings, were synthesized. Quantum chemistry methods have shown that the addition of nitriles and carbon disulfide to indole-2,3-quinodimethane derivatives occurs through cyclic transition states involving a lithium atom. Calculations have substantiated the choice of a non-polar aprotic solvent to increase the yield of γ-carbolines. It has been shown for the first time that the replacement of the oxygen atom in cyclic derivatives of quinodimethane—pyrano[4,3-<i>b</i>]indol-3(5<i>H</i>)-ones by sulfur leads to a complete change in the direction and mechanism of their reaction with dimethyl acetylenedicarboxylate: instead of the usual [4+2] cycloaddition in the case of an oxygen-containing substrate, cascade processes are realized, including alkyne-thiocarbonyl metathesis and [3+2] cycloaddition.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"832-847"},"PeriodicalIF":2.0,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013308","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":"Design, Synthesis and Characterization of Novel (E)-3-(3-Morpholino-1-(m-Tolyl)-5-(Trifluoromethyl)-1\u0000 H-Pyrazol-4-Yl)-N-Phenylacrylamide Derivatives and Their Antimicrobial, Antimalarial and Antitubercular Activities","authors":"Priyesh H. Amin,&nbsp;Rajesh H. Vekariya,&nbsp;Dhanji P. Rajani,&nbsp;Suresh K. Dhakhda","doi":"10.1002/jhet.70042","DOIUrl":"https://doi.org/10.1002/jhet.70042","url":null,"abstract":"<div>\u0000 \u0000 <p>This research investigates the design, synthesis, characterization, and biological assessment of a novel series of (<i>E</i>)-3-(3-morpholino-1-(<i>m</i>-tolyl)-5-(trifluoromethyl)-1<i>H</i>-pyrazol-4-yl)-<i>N</i>-phenylacrylamide derivatives <b>(11a-o)</b>. The compounds <b>(11a-o)</b> were synthesized via a multi-step reaction sequence with 87%–96% yield in the final step and structurally confirmed using advanced spectroscopic techniques, including ¹H-NMR, ¹³C-NMR, FT-IR, and ESI-MS. Analytical data confirm that the compound exhibits a purity of ≥ 95%. The biological evaluation encompassed antimicrobial, antimalarial, and antitubercular activity screening. Antimicrobial assays demonstrated notable antibacterial efficacy, with compounds <b>11h</b> and <b>11j</b> exhibiting superior potency compared to standard antibiotics against \u0000 <i>Escherichia coli</i>\u0000 and \u0000 <i>Staphylococcus aureus</i>\u0000 . Moderate antifungal activity was observed, with compound <b>11d</b> displaying the highest inhibitory effect against <i>Aspergillus niger</i>. In antimalarial studies, compound <b>11i</b> demonstrated exceptional activity (IC50 = 0.25 μg/mL) against <i>Plasmodium falciparum</i>, showing potency comparable to chloroquine. Additionally, compounds <b>11a</b> and <b>11i</b> exhibited significant antitubercular activity against \u0000 <i>Mycobacterium tuberculosis</i>\u0000 H37Rv. A structure–activity relationship (SAR) analysis revealed that specific chemical modifications, particularly electron-withdrawing substitutions and morpholino moieties, played a crucial role in enhancing antimalarial activity. These findings highlight the potential of these derivatives as promising lead compounds for further development into effective therapeutics targeting drug-resistant bacterial, fungal, malarial, and tubercular infections.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"815-831"},"PeriodicalIF":2.0,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013245","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":"Thiazolidinedione-Pyrimidine Hybrid as Potential Antidiabetic Agents and Their Cardioprotective Effect","authors":"Shaista Amin,&nbsp;Faizul Azam,&nbsp;Sayima Nabi,&nbsp;Mohammad Ahmed Khan,&nbsp;Anam Abdullah,&nbsp;M. Shaquiquzzaman,&nbsp;Ashif Iqubal,&nbsp;Mymoona Akhter,&nbsp;Sharba Tasneem,&nbsp;Suruchi Khanna,&nbsp;Prawez Alam,&nbsp;M. Mumtaz Alam","doi":"10.1002/jhet.70021","DOIUrl":"https://doi.org/10.1002/jhet.70021","url":null,"abstract":"<div>\u0000 \u0000 <p>The leading cause of death in diabetic patients is diabetic cardiomyopathy (DCM). Despite the availability of anti-diabetic medications which effectively curb the hyperglycemia, the drug molecule which alleviates the severity of DCM along with the maintenance of a normoglycemic profile of diabetic patients is still unexplored. In this study, a series of thiazolidinedione-pyrimidine hybrid compounds were synthesized, and their anti-diabetic potential was explored in STZ-NA induced diabetic Wistar rats. The role of these compounds in DCM was also evaluated. The most potent compound, PT-5, showed significant reduction in blood glucose levels (from 129 to 115 mg/dL in 2 h) in comparison to the standard drug Pioglitazone (135–117 in 2 h). The biochemical estimations of AST, ALT, ALP, Troponin T, Cκ-MB, CRP, and LDH levels illustrated that the levels appreciably came back to normal in the PT-1, PT-5, and PT-13 treatment groups. The cardioprotective role was further validated by cardiac tropism indices and levels of antioxidants in cardiac tissue. The biochemical assessments were further validated through histopathological studies. This research indicates that these derivatives hold promise for the development of new potential antidiabetic agents.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"791-814"},"PeriodicalIF":2.0,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013173","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":"Structural Design and Synthesis of Cyclosenegalin A Analogue","authors":"Anderson Arnold Aloanis,&nbsp;Tati Herlina,&nbsp;Ari Hardianto,&nbsp;Rani Maharani","doi":"10.1002/jhet.70020","DOIUrl":"https://doi.org/10.1002/jhet.70020","url":null,"abstract":"<div>\u0000 \u0000 <p>Computational approaches have become increasingly popular in peptide synthesis. In this study, we report the computationally assisted design and synthesis of a cyclosenegalin A analogue. The original cyclosenegalin A was previously synthesized with low yield and exhibited no antimicrobial activity. To address these limitations, computational tools such as PEP-FOLD4, iAMPpred, and AI4AMP were employed to design the analogue, aiming to facilitate cyclization and enhance antimicrobial properties. The computational analysis of cyclosenegalin A and its analogs identified <i>c</i>-AVKPGLK as the most promising candidate for further development. It demonstrated strong antimicrobial potential with the highest antibacterial and antifungal activity, along with a compact structure favorable for cyclization. The linear precursor of <i>c</i>-AVKPGLK also formed a stable β-turn structure, making it well-suited for synthesis. The synthesis was conducted using a combination of solid-phase and liquid-phase peptide synthesis. The linear precursor was synthesized using the Fmoc strategy with HATU as the coupling agent and 2-chlorotrityl chloride resin. Head-to-tail cyclization was performed in dilute concentration using a dropwise method with HATU as the coupling agent. The linear precursor synthesis achieved a yield of 97.76%, while the cyclization process yielded 23.38%. The final compound, <i>c</i>-AVKPGLK, was characterized using HR-ToFMS, ¹H NMR, ¹³C NMR, HMQC, HMBC, TOCSY, and ROESY.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"781-790"},"PeriodicalIF":2.0,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013171","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 Comprehensive Report on Environmentally Benign Synthesis of 1, 8-Dioxo-Octahydroxanthene Derivatives","authors":"Avishek Ghatak,&nbsp;Asit Kumar Das,&nbsp;Sanjay Bhar,&nbsp;Amit Pramanik","doi":"10.1002/jhet.70014","DOIUrl":"https://doi.org/10.1002/jhet.70014","url":null,"abstract":"<div>\u0000 \u0000 <p>Heterocycles, especially xanthenediones (1,8-dioxo-octahydroxanthenes), are versatile organic compounds known for their diverse biological properties, including antiproliferative, antibacterial, and antioxidant activities. Despite their potential in treating cancer and neurodegenerative diseases like Alzheimer's, there is a notable lack of literature reports on eco-friendly synthetic approaches for these derivatives. This review aims to fill that gap by highlighting recent advancements in sustainable methodologies, discussing their advantages and limitations. It also explores future prospects and opportunities, providing a comprehensive overview of environmentally friendly synthetic methods for 1,8-dioxo-octahydroxanthenes and their derivatives.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"760-780"},"PeriodicalIF":2.0,"publicationDate":"2025-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013172","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":"Sulfated Polyborate Catalyzed One-Pot, Two-Step, Four-Component Synthesis of Functionalized Pyridines From (Het.)aryl Methyl Ketones","authors":"Shweta S. Gaikwad,&nbsp;Ganesh U. Chaturbhuj","doi":"10.1002/jhet.70035","DOIUrl":"https://doi.org/10.1002/jhet.70035","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel one-pot, two-step, four-component green synthetic route has been developed for the synthesis of substituted pyridine derivatives through intramolecular cyclisation-aromatisation of (Het.)aryl methyl ketones and mono and/or 1,3-dicarbonyl compounds using sulfated polyborate as a catalyst. The catalyst demonstrated rapid and efficient synthesis of a series of substituted pyridine carboxylates, achieving excellent 82%–96% yields within a reaction time of 50–70 min. The reaction mechanism was investigated by studying the order of addition of reactants, revealing the formation of the desired pyridine carboxylate by nucleophilic attack of active methylene on the β-unsaturated carbon of enaminone, followed by intramolecular cyclization and aromatization. A total of 23 structurally diverse substrates were synthesized under moderate reaction conditions, demonstrating a broad substrate scope. The methodology offers several advantages, including high product yields, moderate reaction conditions, absence of hazardous and volatile organic solvents, simple workup process, and environmental friendliness. The synthesized compounds were characterized using melting point, ¹H NMR, and novel compounds were confirmed by ¹³C NMR, direct mass, and elemental analysis.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"752-759"},"PeriodicalIF":2.0,"publicationDate":"2025-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013170","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}