Synthetic Communications最新文献

{"title":"Synthesis and molecular docking studies of new fragrant campholenal derived succinate diesters","authors":"Yeşim Çat (Conceptualization Data curation Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) ,&nbsp;Belkız Bilgin Eran (Conceptualization Validation Visualization Writing – review & editing) ,&nbsp;Akın Sağırlı (Conceptualization Supervision Validation Writing – review & editing) ,&nbsp;Havva Acar (Investigation Visualization) ,&nbsp;Harun Taşdemir (Data curation Resources Visualization) ,&nbsp;Özge Kavas (Data curation Resources Visualization) ,&nbsp;Onur Can Yazıcı (Software Writing – review & editing)","doi":"10.1080/00397911.2026.2626798","DOIUrl":"10.1080/00397911.2026.2626798","url":null,"abstract":"<div><div>Succinate diesters are a versatile class of compounds with diverse applications owing to their unique chemical properties. This study reports the synthesis of novel campholenal-derived succinate diesters, exploiting the structural diversity of campholenal, an important raw material in fragrance chemistry. Monoester succinates were first prepared from low-molecular-weight alcohols and subsequently esterified with campholenol and its <em>α</em>-methyl- and <em>α</em>-dimethyl-substituted derivatives to afford a series of diesters. All intermediates and final products were structurally characterized by IR, NMR, and TOF-LCMS analyses. Olfactory evaluation by an expert panel revealed that propyl-substituted derivatives exhibited enhanced odor longevity, while methyl and dimethyl substitutions on the campholenol moiety significantly influenced odor characteristics. To rationalize these observations at the molecular level, docking studies of compounds <strong>9a–i</strong> were performed against the human olfactory receptor OR51E2. The results supported the experimental findings by indicating favorable binding affinities and interaction patterns for compounds associated with increased odor durability.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 7","pages":"Pages 497-512"},"PeriodicalIF":1.8,"publicationDate":"2026-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147707188","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 structure–activity relationships of chlordimeform imine analogues against Chilo suppressalis","authors":"Xiyan Tang (Investigation Software Validation) ,&nbsp;Lijie Che (Formal analysis Investigation Methodology Validation Writing – original draft) ,&nbsp;Yanmin Huang (Conceptualization Funding acquisition Methodology Project administration) ,&nbsp;Jianguo Cui (Conceptualization Project administration Supervision) ,&nbsp;Zhiping Liu (Conceptualization Investigation Supervision Writing – review & editing)","doi":"10.1080/00397911.2026.2640565","DOIUrl":"10.1080/00397911.2026.2640565","url":null,"abstract":"<div><div>To address the high carcinogenicity of 4-chloro-2-methylaniline (a metabolite of traditional chlordimeform), thirty chlordimeform imine analogues were synthesized using chlordimeform as the lead compound, retaining the core amidine group (–N = CH–N(CH₃)₂) while modifying the benzene ring. The synthesized amidine structures were confirmed by ¹H/¹³C/¹⁹F NMR spectroscopy. Insecticidal activity against resistant <em>Chilo suppressalis</em> was evaluated <em>via</em> the soaked water-oat stem method. At a concentration of 50 μg/mL, compounds <strong>4d</strong>, <strong>4m</strong>, <strong>9c</strong>, and <strong>9d</strong> exhibited a corrected mortality rate of more than 38.67%, which was superior to chlordimeform (22.00%) but significantly lower than that of the commercial insecticide fipronil (88.00%). Preliminary SAR analysis: Retaining the benzene ring’s 2-methyl group and replacing the 4-chloro with fluorine, cyano, phenoxy, or benzyloxy enhanced the insecticidal activity; replacing benzene with heterocycles/fused heterocycles (except pyrazole-substituted <strong>4m</strong>) reduced the insecticidal activity. This study provides theoretical insights and candidate compounds for novel amidine-based insecticides.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 7","pages":"Pages 525-536"},"PeriodicalIF":1.8,"publicationDate":"2026-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147707185","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":"Electrochemical difunctionalization of alkenes via chemoselective oxo-amination to access α-sulfonylamino ketones","authors":"Yu Liu (Validation) ,&nbsp;Xiufeng Zhang (Formal analysis) ,&nbsp;Zhangyang Shen (Data curation) ,&nbsp;Xinyu Bu (Investigation) ,&nbsp;Yingying Deng (Methodology) ,&nbsp;Shengjun Li (Investigation) ,&nbsp;Huanwen Chen (Supervision) ,&nbsp;Pingnan Wan (Data curation) ,&nbsp;Yang Wan (Supervision) ,&nbsp;Sheng Zhang Liu (Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2026.2646265","DOIUrl":"10.1080/00397911.2026.2646265","url":null,"abstract":"<div><div>The oxo-amination of alkenes represents a straightforward route to prepare α-amino ketones, which are valuable scaffolds for organic synthesis. The development of a practical method for this transformation is therefore actively being pursued. Herein, we report an electro-oxidative oxo-amination of alkenes that employs readily available O₂ as a green oxygen source, eliminating the need for an external oxidant. This strategy features a simple setup, broad substrate scope, mild conditions, and high atom economy, enabling the conversion of amines into diversely functionalized α-sulfonylamino ketones. Furthermore, the method was applied to the synthesis of the natural product halostachine. Mechanistic studies suggest a pathway initiated by the electrochemical generation of nitrogen-centred radicals, which subsequently add to alkenes.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 7","pages":"Pages 513-524"},"PeriodicalIF":1.8,"publicationDate":"2026-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147707187","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 and synthesis of benzofuran–pyrazole–triazole hybrids via click chemistry: Antimicrobial, anticancer, ADMET, docking, and DFT studies","authors":"Ila M. Ram (Conceptualization Data curation Resources Writing – original draft) ,&nbsp;Jay B. Maheta (Data curation Resources Writing – review & editing) ,&nbsp;Darshna K. Lakhnotra (Data curation Resources) ,&nbsp;Nargis H. Shaikh (Formal analysis Resources) ,&nbsp;Viral U. Majethiya (Resources) ,&nbsp;Yogesh O. Bhola (Software Supervision Writing – review & editing)","doi":"10.1080/00397911.2026.2642776","DOIUrl":"10.1080/00397911.2026.2642776","url":null,"abstract":"<div><div>Ten novel benzofuran–pyrazole–triazole hybrid compounds <strong>(10a–j)</strong> were synthesized via multistep methodology and characterized by ¹H NMR,¹³ CMR, IR, and mass spectrometry. Molecular docking studies against epidermal growth factor receptor (EGFR) (1M17) and the fibrinogen-binding domain (4NYT) revealed compounds <strong>10i</strong> and <strong>10j</strong> as promising EGFR inhibitors, with binding scores of −6.22 and −6.21 kcal/mol, respectively, which are superior to that of combretastatin-A4 (−6.15 kcal/mol). Against the fibrinogen-binding domain, compounds <strong>10d</strong> and <strong>10h</strong> showed excellent binding (−8.65 kcal/mol each) compared to ciprofloxacin (−7.49 kcal/mol). Anticancer evaluation demonstrated compound <strong>10c</strong> as the most potent with IC₅₀ values of 2.18–2.50 µM against HT-29, MCF-7, and A549 cell lines. Compound <strong>10j</strong> also exhibited significant activity (IC₅₀: 2.61–3.82 µM) across multiple cancer cell lines. Antimicrobial screening revealed that compound 10h exhibited broad-spectrum activity (minimum inhibitory concentration [MIC]: 0.0157–0.0628 mg ml⁻¹), while compounds <strong>10i</strong> and <strong>10j</strong> showed efficacy comparable to that of ciprofloxacin. Density functional theory (DFT) calculations (B3LYP/6–311++G(d,p)) indicated superior thermodynamic stability for compound <strong>10h</strong> over <strong>10j</strong>, absorption, distribution, metabolism, and excretion (ADMET) analysis confirmed acceptable drug-like properties with minimal Lipinski violations. These benzofuran–pyrazole–triazole hybrids represent promising scaffolds for the development of anticancer and antimicrobial drugs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 7","pages":"Pages 537-564"},"PeriodicalIF":1.8,"publicationDate":"2026-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147707184","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":"An isoxazole strategy for the synthesis of curcumin and demethoxycurcumin","authors":"Mirai Kato (Investigation Writing – original draft) ,&nbsp;Kyosuke Sugihara (Investigation) ,&nbsp;Aki Tanaka (Investigation Writing – review & editing) ,&nbsp;Rina Tanaka (Investigation) ,&nbsp;Hitoshi Abe (Conceptualization Project administration Supervision Writing – review & editing)","doi":"10.1080/00397911.2026.2649255","DOIUrl":"10.1080/00397911.2026.2649255","url":null,"abstract":"<div><div>Curcumin and demethoxycurcumin were synthesized <em>via</em> an isoxazole-masking strategy. A 3,5-disubstituted isoxazole, obtained by [3 + 2] cycloaddition of a nitrile oxide and an alkyne, underwent mild reductive <em>N</em>-<em>O</em> cleavage to reveal the β-diketone core in good yield.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 7","pages":"Pages 565-572"},"PeriodicalIF":1.8,"publicationDate":"2026-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147707186","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":"Molecular hybrids integrated with coumarin and oxazepane: Synthesis, biological evaluation, ADME studies and molecular docking","authors":"Dipen Panchani (Methodology Writing – original draft) ,&nbsp;Tirth Harikrishna Thaker (Conceptualization Investigation Project administration Supervision Visualization Writing – review & editing) ,&nbsp;Pratiksha Nigutkar (Methodology) ,&nbsp;Srujal Sonera (Data curation Visualization)","doi":"10.1080/00397911.2026.2636915","DOIUrl":"10.1080/00397911.2026.2636915","url":null,"abstract":"<div><div>Novel coumarin-oxazepane hybrids <strong>3a–b</strong>, <strong>4a–b</strong>, <strong>5a–b</strong> have been synthesized via a cycloaddition reaction strategy. The newly synthesized compound was confirmed based on ¹H NMR, Mass and IR spectroscopic analysis techniques. Further, titled compounds were subjected to <em>in vitro</em> anti-microbial screening against various bacterial strains, such as <em>Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and Bacillus subtilis</em>. Among these, all compounds were found to be most active, equally potent against <em>Escherichia coli</em> and <em>Staphylococcus aureus</em> as compared to the standard drug penicillin. Each compound has a bioavailability score of 55% and a pain assay score of zero, complies with Lipinski’s rule of five, and has high gastrointestinal (GI) absorption. Compounds 5a and 5b show the best docking scores with (PDB IDs: 3ERD and 2DXT), ranging from −10.1 to −10.5 kcalmol⁻¹ compared to standard Warfarin and Adriamycin and potency against HL-60 and MCF-7 cell lines in vitro.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 6","pages":"Pages 459-474"},"PeriodicalIF":1.8,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147553713","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":"Multifunctional metal complexes with mixed ligands: Synthesis, computational insights, and antimicrobial potential","authors":"Amitkumar Bodar (Formal analysis Funding acquisition) ,&nbsp;Jignasa Parmar (Validation Visualization) ,&nbsp;Darshan Jani (Conceptualization Investigation) ,&nbsp;Bansuri Nandaniya (Methodology Software) ,&nbsp;Chintan Somaiya (Resources Validation)","doi":"10.1080/00397911.2026.2643897","DOIUrl":"10.1080/00397911.2026.2643897","url":null,"abstract":"<div><div>In order to create novel mixed ligand transition metal-based coordination compounds, several 2-hydroxy-benzaldehyde derivatives interacted with Schiff bases based on the sulfa drug. The spectroscopic properties and antibacterial properties of the generated compounds and their coordination compounds were studied in detail. The ligands were structurally characterized using ¹H-NMR, IR, mass spectrometry, UV-Vis spectroscopy, and elemental analysis, while the coordination compound’s structure was verified by IR, UV-Visible, and FAB mass spectroscopy. In vitro studies were conducted to assess the effectiveness of the ligands and coordination compounds against Gramme + ve bacteria (<em>B. subtilis</em>, <em>S. epidermidis</em>), Gramme -ve bacteria (<em>E. coli</em>, <em>P. aeruginosa</em>), and fungus (<em>A. niger</em>). The findings highlight the potential of coordination compounds based on transition metals and the necessity for more study in this field.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 6","pages":"Pages 484-495"},"PeriodicalIF":1.8,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147553715","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":"Novel, efficient, and alternative synthesis of a dual endothelin receptor antagonist – macitentan","authors":"Naresh Reddy Kanakanolla (Conceptualization Data curation Formal analysis Investigation Methodology Resources Writing – original draft) ,&nbsp;Anil Kumar Mardhanpally (Conceptualization Formal analysis Methodology Supervision Writing – original draft) ,&nbsp;Subbanarasimhulu Porala (Data curation) ,&nbsp;Naresh Kumar Reddy Kondampally (Data curation) ,&nbsp;Chandrasekhar Byravakunta (Data curation) ,&nbsp;Pavan Kumar Reddy Bandla (Data curation) ,&nbsp;Anil Kumar Bojja (Writing – review & editing)","doi":"10.1080/00397911.2026.2636916","DOIUrl":"10.1080/00397911.2026.2636916","url":null,"abstract":"<div><div>A concise and efficient synthetic route to Macitentan (<strong>1</strong>), a potent endothelin receptor antagonist, has been developed. The strategy involves mono mesylation of 5-(4-bromophenyl) pyrimidine-4,6-diol (<strong>2</strong>), followed by <em>O</em>-alkylation with <em>O</em>-substituted ethylene chloride (<strong>13</strong>) to generate a key novel intermediate <strong>14</strong>, which is on nucleophilic substitution with <em>n</em>-propyl sulfamide (<strong>15</strong>), furnishes macitentan, effectively suppressing the generation of the highly potent disubstitution product. This approach involves the key novel intermediates, hydroxy <em>O</em>-mesyl (<strong>11</strong>), <em>O</em>-substituted ethylene chloride (<strong>13</strong>), and <em>O</em>-mesyl ethoxy pyrimidine (<strong>14</strong>). This approach enables complete control over disubstitution product formation, resulting in a significant improvement in overall yield (73%). The developed process offers operational simplicity and scalability, making it suitable for commercial manufacturing of macitentan.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 6","pages":"Pages 451-458"},"PeriodicalIF":1.8,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147553712","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":"Iridium-mediated N–H alkylation of pyrrolo[2,3-d] pyrimidines with trifluoromethylcyclo[1.1.1]pentylthianthrenium salts","authors":"Bin Liu (Investigation Methodology Writing – original draft) ,&nbsp;Jiangrong Wang (Investigation Methodology Writing – original draft) ,&nbsp;Jiaqi Tong (Investigation) ,&nbsp;Xingxian Zhang (Conceptualization Funding acquisition Project administration Supervision Writing – review & editing)","doi":"10.1080/00397911.2026.2633767","DOIUrl":"10.1080/00397911.2026.2633767","url":null,"abstract":"<div><div>A variety of novel CF₃BCP-substituted pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was synthesized <em>via</em> visible light-induced Iridium-catalyzed N–H alkylation using CF₃BCP^-TT⁺ salt as the alkylating reagent in moderate to good yields under mild reaction conditions. This protocol provides a practical and effective strategy for the functional modification of pyrrolo[2,3-<em>d</em>]pyrimidines scaffold for the further biological evaluation.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 6","pages":"Pages 475-483"},"PeriodicalIF":1.8,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147553714","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":"Recent advances for the synthesis of dihydropyrimidines through Biginelli-like reactions based on in situ prepared aldehydes","authors":"Samir Y. Abbas (Data curation Investigation Project administration Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2026.2619481","DOIUrl":"10.1080/00397911.2026.2619481","url":null,"abstract":"<div><div>Dihydropyrimidinones have a variety of pharmacological and ­therapeutic uses. The Biginelli reaction is the cyclocondensation of aldehydes, urea, and acetoacetic ester that produces 3,4-dihydropyrimidine-2-ones. Because of the substantial biological and pharmacological benefits of dihydropyrimidinones, the Biginelli reaction has consistently received attention. The dihydropyrimidines were synthesized <em>via</em> modification of classical Biginelli substrates using aldehyde alternatives. The alcohols, halogenated and methyl arenes, are inexpensive and abundant in nature. Therefore, the alcohols, halogenated and methyl arenes, were used as surrogates of aldehydes in the environmentally friendly production of dihydropyrimidines. So, the topic of this review is the synthesizing of dihydropyrimidines using a Biginelli-like reaction based on <em>in situ</em>-prepared aldehydes and urea/thiourea.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 6","pages":"Pages 437-450"},"PeriodicalIF":1.8,"publicationDate":"2026-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147553716","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}