Journal of Heterocyclic Chemistry最新文献

{"title":"Design, Synthesis, and Insecticidal Evaluation of Neonicotinoid Analogues With 1,2-Dihydropyridine Scaffold","authors":"Du Tan,&nbsp;Yiping Wang,&nbsp;Wulin Yang,&nbsp;Xusheng Shao,&nbsp;Zhong Li","doi":"10.1002/jhet.70028","DOIUrl":"https://doi.org/10.1002/jhet.70028","url":null,"abstract":"<div>\u0000 \u0000 <p>A series of neonicotinoid analogues with 1,2-dihydropyridine scaffold were synthesized by the novel annulation reaction. Bioassay indicated that some compounds exhibited good insecticidal activity against <i>Aphis craccivora</i> at a concentration of 100 mg/L, and the substituents on the phenyl group have a great influence on insecticidal activity. Especially, the LC₅₀ values of compounds <b>A3</b> and <b>A19</b> were 17.089 and 4.792 mg/L, respectively. Molecular docking results revealed that compound <b>A19</b> bound to <i>Lymnaea stagnalis</i> acetylcholine binding protein via H-bonds with the residues of Leu102, Val114, and Arg55. These results proposed a promising guide for the design of neonicotinoid analogues with 1,2-dihydropyridine scaffold.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"1050-1058"},"PeriodicalIF":2.0,"publicationDate":"2025-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196578","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 Synthesis of Alkoxypyrazole- or Pyrazolone-Fused 1,4-Naphthoquinones via Ullmann Cyclization and Evaluation of Their Cytotoxicity","authors":"Kyungmin Kim,&nbsp;Hyunjin Lee,&nbsp;Yunseung Kuk,&nbsp;Hongil Jo,&nbsp;Kang Min Ok,&nbsp;Tae Hoon Lee,&nbsp;Hakwon Kim","doi":"10.1002/jhet.70047","DOIUrl":"https://doi.org/10.1002/jhet.70047","url":null,"abstract":"<div>\u0000 \u0000 <p>A series of novel 3-alkoxypyrazole- and pyrazolone-fused 1,4-naphthoquinone derivatives were successfully synthesized through an intramolecular Ullmann-type cyclization, using 1,4-dihydroxy-2-naphthoic acid as the starting material. Subsequent regioselective <i>N</i>- or <i>O</i>-alkylation followed by CAN-mediated oxidation afforded the desired quinones in moderate to good yields. The molecular structures of the selected <i>N</i>-substituted derivatives were unambiguously confirmed by single-crystal X-ray diffraction. Preliminary cytotoxicity against RAW264.7 cells revealed that biological activity varied depending on the nature of substitution, with certain compounds exhibiting potent effects (LD₅₀ &lt; 5 μM). These findings highlight the potential of fused heterocycles as promising lead structures for anticancer drug development.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"1059-1073"},"PeriodicalIF":2.0,"publicationDate":"2025-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196576","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":"Synthesizing Novel Imidazole-Conjugated Cyclic Sulfone Derivatives With Amide Fragments and Evaluating Their Insecticidal Activities","authors":"Daoxin Wu,&nbsp;Xinlin Li,&nbsp;Juncheng Xiang,&nbsp;Yunfeng Yao,&nbsp;Yu Yan,&nbsp;Liang Lv,&nbsp;Minhua Liu","doi":"10.1002/jhet.70050","DOIUrl":"https://doi.org/10.1002/jhet.70050","url":null,"abstract":"<div>\u0000 \u0000 <p>In an effort to identify novel insecticides, we designed and synthesized a series of sulfone compounds incorporating amide fragments, based on the lead compound oxazosulfyl. All synthesized compounds were characterized by ¹H NMR, ¹³C NMR, and HR-MS spectroscopic techniques. The insecticidal activity of these compounds was evaluated against <i>Plutella xylostella</i> and <i>Mythimna separata</i> at concentrations of 1 mg/L (<i>P. xylostella</i>: 0%–100%; <i>M. separata</i>: 75%–100%) and 0.1 mg/L (<i>P. xylostella</i>: 0%–30%; <i>M. separata</i>: 0%–65%). Additionally, <i>Aphis craccivora</i> was tested for insecticidal activity at concentrations of 100 mg/L (<i>A. craccivora</i>: 0%–100%) and 10 mg/L (<i>A. craccivora</i>: 0%–100%). Preliminary bioactivity assessments showed that most compounds exhibited potent insecticidal activity against <i>P. xylostella</i> and <i>M. separata</i> at 1 mg/L, and against <i>A. craccivora</i> at 100 mg/L. Especially, the compound <b>9d</b>, N-(3-bromo-5-(ethylsulfonyl)-6-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-yl)-N-(cyclopropanecarbonyl)cyclopropanecarboxamide (<b>9d</b>), demonstrated remarkable insecticidal activity at a concentration of 1 mg/L, resulting in 100% mortality in both <i>P. xylostella</i> and <i>M. separata</i>. Its activity against <i>M. separata</i> surpassed that of oxazosulfyl (<i>M. separata</i>: 0%) and matched cyproflanilide (<i>M. separata:</i> 100%). Even at a lower concentration of 0.1 mg/L, it achieved 50% mortality in <i>M. separata</i>, indicating excellent insecticidal activity. Against <i>A. craccivora</i> at 100 mg/L, it also showed 100% mortality, comparable to imidacloprid. Based on the insecticidal experiments, preliminary structure–activity relationships were investigated and discussed. The findings suggest that sulfone compounds containing amide structural fragments have the potential to be developed into novel insecticides.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"1041-1049"},"PeriodicalIF":2.0,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196554","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 Biological Activity of Chalcone Derivatives Containing Thiazoxime Ethers","authors":"Yishan Qin,&nbsp;Nan Sun,&nbsp;Jieyu Li,&nbsp;Han Yang,&nbsp;Haotao Pu,&nbsp;Yuhong Wang,&nbsp;Xingping Luo,&nbsp;Jing Zhang,&nbsp;Wei Xue","doi":"10.1002/jhet.70046","DOIUrl":"https://doi.org/10.1002/jhet.70046","url":null,"abstract":"<div>\u0000 \u0000 <p>In this paper, a series of chalcone derivatives containing thiazole oxime ether structures were designed and synthesized from the natural product chalcone. The structures of these compounds were characterized using nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The results of antiviral activity tests showed that some of the target compounds exhibited better inhibition. Among them, <b>S3</b>, <b>S4</b>, and <b>S16</b> exhibited better therapeutic activities with EC₅₀ values of 18.6, 66.9, and 61.8 μg/mL, respectively, which were superior to that of the control drug ningnanmycin (158.3 μg/mL). The target compound <b>S3</b> showed good protective activity with an EC₅₀ of 88.6 μg/mL, which was better than that of ningnanmycin (175.6 μg/mL). The results of microscale thermophoresis (MST) demonstrated that <b>S3</b> and <b>S13</b> exhibited strong binding affinity to tobacco mosaic virus capsid protein (TMV-CP), with Kd values of 0.0013 μM and 0.5397 μM, respectively. These values were significantly lower than that of ningnanmycin (Kd = 0.6509 μM). The molecular docking results showed that the hydrogen bonds between <b>S3</b> and the key amino acid residues of TMV-CP had shorter bond lengths and were more tightly bound than those of ningnanmycin.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"1029-1040"},"PeriodicalIF":2.0,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196615","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":"Advances in Construction of N-Heterocycles via Electrochemical Methods","authors":"Arathi T. Parambu,&nbsp;Amritha Ayyaruthodi,&nbsp;Gopika Kannanthra,&nbsp;Thachapully D. Suja","doi":"10.1002/jhet.70041","DOIUrl":"https://doi.org/10.1002/jhet.70041","url":null,"abstract":"<div>\u0000 \u0000 <p>Nitrogen heterocycles constitute the core structural units of many natural products and pharmaceutically relevant man-made compounds. Their importance and demand have led to the development of a number of classical methods for their synthesis. The continued search for more efficient, greener, and practical methods has led to the adoption of non-conventional approaches too. Electroorganic synthesis is one such approach, which has gained huge popularity in recent years, mainly due to the ready availability of compact reaction set-ups. Electrochemical reactions generally proceed under ambient conditions with good atom economy and better E-values. Occasionally, a few transformations that were impossible using the traditional reagents were realized by the judicious combination of electrodes, electrolytes, and substrates. The recent developments in the area are summarized here. Each section is devoted to detailed discussions on electrochemical reactions that installed the important <i>N</i>-heterocycle it is titled after.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"1012-1028"},"PeriodicalIF":2.0,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196614","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, Anticancer and Antiadipogenic Activity of Curcumin Linked 1,2,3,4-Tetrazole Derivatives","authors":"Begari Nagaraju,&nbsp;Rallapati Prathibha,&nbsp;Mothukuri Balaguraiah,&nbsp;Reddy-Sankaran Karunakaran,&nbsp;Vaddamanu Shanmuga Kumar,&nbsp;Prashantha Karunakar,&nbsp;Meriga Balaji,&nbsp;Chunduri Venkata Rao,&nbsp;Suresh Maddila","doi":"10.1002/jhet.70051","DOIUrl":"https://doi.org/10.1002/jhet.70051","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel series of monocarbonyl analogs of curcumin linked to 1,2,3,4-tetrazole analogs were designed, synthesized, and characterized by ¹H NMR, ¹³C NMR, FT-IR, and mass spectral analysis. Further, all the target molecules were aimed at investigating the effect of curcumin analogs on preventing breast cancer cells and adipogenesis activity. In vitro cytotoxic properties of curcumin analogs were evaluated by MTT assay, while antiadipogenic activity was assessed by Oil-Red O staining and lipolysis. Compounds <b>7g</b>, <b>7m</b>, <b>7d</b>, and <b>7l</b> have noteworthy anticancer activity in vitro against the MCF-7 cell line, with IC₅₀ values of <b>20.39</b>, <b>21.11</b>, <b>33.81</b>, and <b>37.01</b> μg/mL, in that order. Additionally, the same compounds (<b>7g</b>, <b>7m</b>, <b>7d</b>, and <b>7l</b>) exhibited good adipogenesis activity with the value of (<i>p</i> &lt; 0.001) at a dose of 40 μg/mL and lipid accumulation in 3T3-L1 cells. Furthermore, molecular docking analysis was established, and these active compounds showed effective bonding interactions. Thus, based on the results, the study suggests that these monocarbonyl analogs of curcumin hybrids could be promising compounds for the treatment of breast cancer and the prevention of adipogenesis.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"994-1011"},"PeriodicalIF":2.0,"publicationDate":"2025-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145197343","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":"I2-Mediated Mild Synthesis of Benzothiadiazine 1,1-Dioxide Derivatives From Aminobenzamides and Aldehydes","authors":"Dongxiao He,&nbsp;Yu Zhou,&nbsp;Yue Wu,&nbsp;Qiuzhu Chen,&nbsp;Wei Li,&nbsp;Wei Wang,&nbsp;Zongjie Gan","doi":"10.1002/jhet.70049","DOIUrl":"https://doi.org/10.1002/jhet.70049","url":null,"abstract":"<div>\u0000 \u0000 <p>An environmentally benign and transition metal-free oxidative cyclization method has been developed for the one-pot synthesis of benzothiadiazine 1,1-dioxide derivatives, utilizing molecular iodine (I₂) as the sole oxidant from commercially available aldehydes and 2-aminobenzenesulfonamides. The protocol features a wide substrate scope and simple operation, providing easy access to a range of benzothiadiazine 1,1-dioxide derivatives in moderate to good yields.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 10","pages":"984-993"},"PeriodicalIF":2.0,"publicationDate":"2025-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145197342","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":"Diversified Synthetic Strategies of Quinoline and Its Derivatives: A Review","authors":"Kapil Kumar,&nbsp;Sachin Puri,&nbsp;Vikrant Abbot","doi":"10.1002/jhet.70048","DOIUrl":"https://doi.org/10.1002/jhet.70048","url":null,"abstract":"<div>\u0000 \u0000 <p>Quinoline is one of the heterocyclic scaffolds that have nitrogen at the first position. Recently, quinoline scaffolds were found to play a vital role in medicinal chemistry due to their low cytotoxicity and diverse biological applications. Heterocycles quinoline compounds have shown a wide spectrum of pharmacological activities that have been successfully screened for anti-inflammatory, anticancer, antimalarial, and antibacterial potency. Due to the biological and pharmacological activities of quinoline and their derivatives, several different strategies have been developed for the synthesis of the ring. This article aims to highlight syntheses using various protocols for the development of quinoline derivatives.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"944-973"},"PeriodicalIF":2.0,"publicationDate":"2025-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013221","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":"Solid-Phase Synthesis of 1,3,5,6-Tetra-Substituted 3,5-Dihydroimidazo[4,5-c][1,2]Thiazin-4(1\u0000 H)-One 2,2-Dioxide Derivatives","authors":"Jimin Moon,&nbsp;Hyojin Lee,&nbsp;Sohee Kim,&nbsp;Taeho Lee","doi":"10.1002/jhet.70045","DOIUrl":"https://doi.org/10.1002/jhet.70045","url":null,"abstract":"<p>The synthesis of 1,3,5,6-tetra-substituted 3,5-dihydroimidazo[4,5-<i>c</i>][1,2]thiazin-4(1<i>H</i>)-one 2,2-dioxide derivatives was optimized through solid-phase synthesis. Synthetic strategies such as Merrifield resin, Thorpe-Ziegler reaction, Mitsunobu reaction, intramolecular cyclization, and desulfonative nucleophilic substitution were employed to synthesize a total of 31 derivatives. The synthesis showed high yields of 72%–87% per step over 8 steps, resulting in an overall yield of 7%–33%, thereby developing an efficient synthetic route for the derivatives.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"938-943"},"PeriodicalIF":2.0,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.70045","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013102","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":"Thiazolidinedione Derivatives as Anticancer Agents: Synthetic Strategies, SAR, and Therapeutic Potential","authors":"Biplab Debnath,&nbsp;Samiran Paul,&nbsp;Sandip Kumar Pahari,&nbsp;Bikram Nandi,&nbsp;Swarup Manna,&nbsp;Arindam Maity,&nbsp;Richa Dayaramani,&nbsp;Sayan Bhattacharjee,&nbsp;Krishnalekha Bandyopadhyay,&nbsp;Nigam Jyoti Maiti,&nbsp;Shah Alam Khan,&nbsp;Md Jawaid Akhtar,&nbsp;Rajarshi Nath","doi":"10.1002/jhet.70044","DOIUrl":"https://doi.org/10.1002/jhet.70044","url":null,"abstract":"<div>\u0000 \u0000 <p>Cancer is the second most common cause of mortality after cardiovascular diseases. Over the years, many chemotherapeutic agents have been developed, but the lack of target specificity and selectivity, toxicity to normal cells, and the problem of developing resistance limit their clinical usefulness. This has prompted the search for novel, safer, effective, and highly specific anticancer agents. Thiazolidinedione, a sulfur and nitrogen-containing five-membered heterocyclic ring, has shown promising anticancer potential in preclinical studies. Substitutions at different positions on the thiazolidinedione scaffold can overcome the problem of toxicity and drug resistance by targeting cancer with various mechanisms of action. This includes promoting apoptosis of the cancer cells, inhibiting signaling pathways, and cell proliferation in cancers by the activation of peroxisome proliferator-activated receptor gamma (PPAR-γ). The thiazolidinedione derivatives also act by inhibiting glyoxalase, TopI/II, GLUT, Bcl2, Ras/Raf, and tyrosine kinase involved in cancer pathogenesis. This review discusses the recent developments in synthetic strategies of thiazolidinedione scaffolds; their mechanism of action, anticancer potential, and structure–activity relationships (SAR) will provide guidance for future directions in cancer research. The recent advancements in the development of thiazolidinedione derivatives as anticancer agents will pave the way for medicinal chemists to direct the synthesis of novel thiazolidinedione derivatives for future clinical use.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 9","pages":"906-937"},"PeriodicalIF":2.0,"publicationDate":"2025-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145013231","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}