Synthetic Communications最新文献

{"title":"New thiazole-based pyrazolo[1,5-a]pyrimidine hybrids: One-pot synthesis of potential MRSA and VRE inhibitors","authors":"Ahmed A. M. Ahmed (Conceptualization Data curation Formal analysis Funding acquisition Supervision) ,&nbsp;Ahmed E. M. Mekky (Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) ,&nbsp;Sherif M. H. Sanad (Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2475901","DOIUrl":"10.1080/00397911.2025.2475901","url":null,"abstract":"<div><div>Synthesis of new heterocyclic hybrids that are capable of fighting methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) and vancomycin-resistant <em>Enterococcus</em> (VRE) strains is still a challenging task for organic chemists. In the current study, we examined the protocol involving the reaction of 2-(4-arylthiazol-2-yl)acetonitriles and benzaldehyde in pyridine at reflux for 2 h. The reaction mixture was then treated with 1<em>H</em>-pyrazole-3,5-diamines and heated at reflux for an additional 3-4 h. The reaction afforded 15 new thiazole-linked pyrimidines in good to excellent yields. Product <strong>3e</strong>, which is linked to 4-methoxybenzyl and 4-(4-methoxyphenyl)thiazol-2-yl) units at C3 and C6, respectively, displayed the best antibacterial efficacy, especially against <em>Staphylococcus aureus</em> and <em>Enterococcus faecalis</em>, with an MIC/MBC up to 1.8/3.6 µM. Moreover, it possessed comparable efficacy to linezolid with an MIC/MBC of 3.6/7.3 µM against VRE ATCC:51299 and ATCC:51575, whereas it had an MIC/MBC of 7.3/14.6 µM against MRSA ATCC:33591 and ATCC:43300.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 7","pages":"Pages 550-562"},"PeriodicalIF":1.8,"publicationDate":"2025-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609233","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":"Green synthesis of oxadiazolo[2,3-b]quinazolin-5-ones based on iodine-catalyzed cyclodesulfurization in water","authors":"Yuuki Tomotani (Investigation) ,&nbsp;Shinji Tanimori (Methodology Project administration)","doi":"10.1080/00397911.2025.2473056","DOIUrl":"10.1080/00397911.2025.2473056","url":null,"abstract":"<div><div>Oxadiazolo[2,3-<em>b</em>]quinazolin-5-ones are a rare class of heterocycles exhibiting herbicidal and fungicidal activities. We found that the cyclodesulfurization of 2-thioxo-3(2<em>H</em>)-quinazolinyl)benzamides prepared from methyl 2-isothiocyanatobenzoates and benzoylhydrazines afforded oxadiazolo[2,3-<em>b</em>]quinazolin-5-ones by the mediation of catalytic iodine in moderate to excellent yields. The reactions proceeded smoothly in water with the presence of terminal oxidant and base under mild reaction conditions.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 7","pages":"Pages 544-549"},"PeriodicalIF":1.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609232","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":"Microwave assisted, one-pot four component designing of 1-butyl-4,5-bis(4-chlorophenyl)-2-aryl-1H-imidazoles","authors":"Antar A. Abdelhamid (Conceptualization Data curation Formal analysis Investigation Methodology Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) ,&nbsp;Raafat A. El-Eisawy (Conceptualization Investigation Methodology Writing – review & editing) ,&nbsp;Nawaf I. Alsenani (Funding acquisition Project administration Resources Validation) ,&nbsp;Esam A. Alqurashi (Funding acquisition Project administration Software) ,&nbsp;Abdulrahman A. Alsimaree (Conceptualization Funding acquisition Methodology Writing – review & editing) ,&nbsp;Musa E. Mohamed Babiker (Investigation Methodology Supervision Validation) ,&nbsp;Amer A. Amer (Conceptualization Data curation Investigation Methodology Resources Writing – original draft Writing – review & editing) ,&nbsp;Faleh Z. Alqahtany (Formal analysis Funding acquisition Project administration Resources Validation Writing – review & editing) ,&nbsp;Mohamed G. Badrey (Data curation Investigation Methodology Writing – review & editing)","doi":"10.1080/00397911.2025.2472375","DOIUrl":"10.1080/00397911.2025.2472375","url":null,"abstract":"<div><div>A novel series of 1-butyl-4,5-bis(<em>p</em>-chlorophenyl)-2-phenyl-1H-imidazole derivatives <strong>5–14</strong> were prepared via one-pot cyclo-condensation of aryl aldehyde derivatives, butylamine, 1,2-bis(4-chlorophenyl)-1,2-ethanedione &amp; CH₃COONH₄, undergo microwave irradiation employing 4-methylbenzenesulfonic acid (PTSA) as acidic catalyst. Also, the same compounds 1,2,4,5-tetrasubstituted-1H-imidazole products <strong>5–14</strong> were designed under thermal reaction condition. By optimizing the two-reaction method, it was found that under conventional condition (reflux method), the identical products <strong>5–14</strong> were generated in good yields (68–87%) in about 10 h. While using the microwave irradiation is an effective and clean technique than the traditional thermal method and gives the same products with higher yields (71–89%) and purity in less time (7–9 min). Additionally, we find that the concentration of <em>p</em>-toluenesulfonic acid affects both the reaction time and the yield. The structures of the prepared components were approved via Infrared spectra, Nuclear Magnetic Resonance and elementals analysis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 7","pages":"Pages 536-543"},"PeriodicalIF":1.8,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609231","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 efficient synthesis of novel tricyclic fused pyrido[3,2-e]thiazolo[3,2-a]pyrimidines via one-pot three-component reaction in a green media","authors":"Sajedeh Alizadeh (Data curation Methodology Writing – original draft) ,&nbsp;Abbas Ali Esmaeili (Investigation Project administration Supervision Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2470850","DOIUrl":"10.1080/00397911.2025.2470850","url":null,"abstract":"<div><div>In this study, we report the development of an efficient and facile synthetic approach for the preparation of novel pyrido[3,2-e]thiazolo[3,2-a]pyrimidines via a tandem Knoevenagel–Michael cyclo-condensation reaction. This transformation employs heterocyclic enamine, aromatic aldehydes, and malononitrile in the presence of DABCO as an organocatalyst under ethanol reflux conditions. The reactions proceed to completion within 1.0–1.5 h, affording the desired products in good to high yields (75%–82%). The main goal of this study is to design and synthesize heterocyclic scaffolds that exhibit promising biological activity. Notable benefits of this approach include a simple work-up procedure, environmentally friendly conditions, and the use of an inexpensive and readily accessible catalyst. The structures of the target compounds (<strong>4a–j</strong>) were validated using IR, ¹H, and ¹³C NMR spectroscopy, mass spectrometry, and elemental analysis, demonstrating the effectiveness and practicality of the method developed.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 7","pages":"Pages 563-575"},"PeriodicalIF":1.8,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609229","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, computational studies and in-silico antimicrobial evaluation of novel N-(substituted) sulfonyl carboxamide bearing pyrrolidine-2,5-dione","authors":"Chafika Bougheloum ,&nbsp;Soumaya Bouskia","doi":"10.1080/00397911.2025.2468985","DOIUrl":"10.1080/00397911.2025.2468985","url":null,"abstract":"<div><div>Novel <em>N</em>-(substituted) sulfonyl carboxamides containing pyrrolidine-2,5-dione or alkyl(aryl)amine moieties, along with some of the intramolecular cyclization derivatives, have been synthesized, designed, and predicted as effective antimicrobial agents. All structures were confirmed by mass spectroscopy,¹H NMR, ¹³C NMR, IR and elemental analysis. Using the DMol³/DFT tool in the Material Studio package, the new carboxamide structures were optimized. The HOMO-LUMO energy gap and the molecular electrostatic potential (MEP) are assessed through density functional calculations. In molecular docking, the studied compounds demonstrated good binding score values (up to −10.0 Kcal/mol) for the active site of tyrosyl-tRNA synthetase protein (PDB ID: 1JIJ) when compared to drugs ciprofloxacin and sulfamethoxazole (−8.5 and −8.0 Kcal/mol, respectively). Notably, compound 2,5-dioxo-<em>N</em>-((4-phenylpiperazin-1-yl)sulfonyl)pyrrolidine-1-carboxamide (<strong>1e</strong>) demonstrated the highest efficiency, making it a promising antibacterial candidate according to DFT and molecular docking studies. Pharmacological characteristics, including drug similarity and oral bioavailability, have been ascertained using Lipinski’s rule of five. Also, some web tools were used to predict the biological activity of synthesized compounds. The findings indicated potential biological targets and good bacterial activity.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 6","pages":"Pages 496-520"},"PeriodicalIF":1.8,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521108","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":"Room-temperature aerobic oxidation of alcohols into carbonyl compounds using VO@GO catalyst","authors":"Sahana Raju ,&nbsp;Kothanahally S. Sharath Kumar ,&nbsp;Yarabhally R Girish ,&nbsp;Turuvekere Krishnamurthy Chaitra ,&nbsp;Mohd Sajid Ali ,&nbsp;Hamad A. Al-Lohedan","doi":"10.1080/00397911.2025.2461114","DOIUrl":"10.1080/00397911.2025.2461114","url":null,"abstract":"<div><div>A reusable catalyst is better alternative to the transition metal-free conditions promoted organic transformations. Herein, we present a VO@GO catalyst for the specific conversion of alcohols into aldehydes or ketones. The catalyst works at room temperature and enables controlled oxidation. The catalyst activity is attributed to the synergistic effect of combining graphene oxide (GO) with vanadium. This method stands out for its high yields, single-step process, broad substrate scope, gentle reaction conditions, wide functional groups tolerance, catalyst reusability, and easy purification.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 6","pages":"Pages 465-475"},"PeriodicalIF":1.8,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521104","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":"Three-component one-pot construction of 2-aryl-3-benzylbenzo[4,5]imidazo[1,2-a]pyrimidines using solid calcium carbide as an alkyne source","authors":"Jiao Wang ,&nbsp;Zhiqiang Wang ,&nbsp;Botao Wang ,&nbsp;Zheng Li ,&nbsp;Jinhui Yang","doi":"10.1080/00397911.2025.2466015","DOIUrl":"10.1080/00397911.2025.2466015","url":null,"abstract":"<div><div>A concise method for the construction of 2-aryl-3-benzylbenzo[4,5]imidazo[1,2-<em>a</em>]pyrimidines using solid calcium carbide as an alkyne source, 2-aminobenzimidazoles, and (hetero)aromatic aldehydes as substrates through one-pot three-component procedure is described. The target products were effectively obtained through A³ coupling, 6-<em>endo-dig</em> cyclization, isomerization, and dehydration cascade processes. The salient features of this protocol are the use of an inexpensive, abundant and easy-to-handle solid alkyne source instead of flammable and explosive gaseous acetylene, low-cost catalyst, wide functional tolerance, satisfactory yield, and simple workup procedure. The reactions can also be carried out on a gram scale.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 6","pages":"Pages 485-495"},"PeriodicalIF":1.8,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521105","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":"Visible light induced deaminative alkylation of pentafluorostyrene promoted by EDA complex","authors":"Bei-Lei Wang ,&nbsp;Lin-Yuan Zeng ,&nbsp;Pei-Zhen Qu ,&nbsp;De-Zhi Yang","doi":"10.1080/00397911.2025.2462668","DOIUrl":"10.1080/00397911.2025.2462668","url":null,"abstract":"<div><div>Polyfluoroaromatic compounds are important components in medicinal and material science, however, methodologies for the synthesis of alkylated pentafluoroarenes remains limited. Here we developed a deaminative coupling reaction of Katritzky salts with pentafluorostyrene to construct C₆F₅-C(sp³) bonds promoted by the photochemical activity of electron donor-acceptor (EDA) complexes. This method features simple reaction conditions, a broad substrate scope, and good functional group tolerance.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 6","pages":"Pages 476-484"},"PeriodicalIF":1.8,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521106","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 antiproliferative evaluation of novel chrysin selenocyanates","authors":"Zhiping Liu ,&nbsp;Lijie Che ,&nbsp;Yunlong Ban ,&nbsp;Maixia Liu ,&nbsp;Xiyan Tang ,&nbsp;Yanmin Huang ,&nbsp;Jianguo Cui ,&nbsp;Chunfang Gan","doi":"10.1080/00397911.2024.2445860","DOIUrl":"10.1080/00397911.2024.2445860","url":null,"abstract":"<div><div>Selenocyano fragments with distinct structural characteristics were successfully incorporated into the 5- and 7-positions of chrysin via etherification and esterification of its hydroxyl groups. Eleven novel chrysin selenocyanates were synthesized, and their structures characterized by NMR and HRMS. The activities of all compounds were evaluated against human cervical cancer cell lines HeLa, ovarian cancer cell lines SKOV-3, and breast carcinoma cell lines MCF-7 using MTT assays. Results indicated that esterified chrysin derivatives significantly inhibited HeLa cells, while alkylated chrysin ethers showed notable activity against SKOV-3 and MCF-7 cells. Compounds <strong>5c</strong> and <strong>5e</strong> exhibited the strongest inhibitory effects on SKOV-3 cells, with IC₅₀ values of 2.27 ± 0.19 μM and 2.51 ± 0.33 μM, respectively. The introduction of diselenocyanate at both the 5- and 7-positions demonstrated superior inhibitory activity compared to a single selenocyanate at the 7-position alone. The findings may aid in designing novel chemotherapeutic drugs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 259-269"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097177","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":"One-pot multicomponent reaction: Synthesis, characterization and antibacterial evaluation of novel tri and tetra-substituted imidazoles","authors":"Bahgat R. M. Hussein ,&nbsp;Hayam H. Mohammed ,&nbsp;Eman A. Ahmed ,&nbsp;Omran A. Omran","doi":"10.1080/00397911.2024.2447087","DOIUrl":"10.1080/00397911.2024.2447087","url":null,"abstract":"<div><div>Using one-pot multicomponent reactions, two new series of imidazoles (<strong>4a–o</strong> and <strong>6a–d</strong>), were synthesized due to their great biological activity. The first series was accomplished by the reaction of <em>O</em>-alkyl vanillins <strong>1a–c</strong>, ammonium acetate <strong>2</strong>, and benzil derivatives <strong>3a–e</strong> in ethanol, while the second series was obtained by reacting <em>O</em>-alkyl vanillins <strong>1a</strong>, ammonium acetate <strong>2</strong>, benzil <strong>3a</strong>, and amino compounds (aniline <strong>5a</strong> or amino acids <strong>5b–d</strong>) in acetic acid. The <em>in vitro</em> antibacterial activity of the novel synthetic imidazoles was assessed against strains of gram positive bacteria, such as <em>Bacillus cereus</em> and <em>Staphylococcus aureus</em>, and gram negative bacteria, such as <em>Pseudomonas aeruginosa</em> and <em>Escherichia coli</em>. The findings indicated that some of the evaluated items have promising antibacterial agents, especially imidazoles <strong>4d</strong> and <strong>4e</strong> for (+G) bacteria and imidazoles <strong>4c</strong> and <strong>4f</strong> for (−G) bacteria.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 270-280"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097171","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}