{"title":"Synthesis, crystal structures and antimicrobial activities of 3-methyl and 3-bromo substituted benzo[b]thiophene based thiosemicarbazones","authors":"Emine Öztürk , Elif Subaşı , Ece Su Çakmakçı , Aslı Şahiner , Betül Şen Yüksel","doi":"10.1080/17415993.2023.2260916","DOIUrl":null,"url":null,"abstract":"<div><p>A series of thiosemicarbazones (TSCs) (<strong>L</strong><sup>1–5</sup>) containing benzothiophen moiety were prepared via the reaction of 3-methyl/3-bromobenzo[b]thiophene-2-carboxaldehyde with appropriate thiosemicarbazides. The compounds were confirmed by elemental analysis, FT-IR, <sup>1</sup>H NMR, MALDI-TOF and single crystal X-Ray diffraction techniques. The compounds exist in the E conformation with respect to the azomethine C = N double bond as confirmed by their C8/C9/N1/N2 torsion angles being 178.4(2)° (<strong>L</strong><sup>1</sup>), – 175.2(5)/177.4(5)° (<strong>L</strong><sup>2</sup>), 177.5(2)° (<strong>L</strong><sup>3</sup>), 179.7(3)° (<strong>L</strong><sup>4</sup>), and – 177.4(7)° (<strong>L</strong><sup>5</sup>). These compounds were researched for their antibacterial activity against Gram-positive bacteria (<em>E. faecalis</em> and <em>S. aureus</em>), Gram-negative bacteria (<em>E. coli, P. aeruginosa</em> and <em>S. marcescens</em>) and antifungal activity against a yeast species <em>C. albicans</em>. The ligands possessed varying degrees of antimicrobial activity. Generally, the compounds demonstrated higher efficacy against gram-positive bacteria than gram-negative ones. The antifungal activity of the compounds against <em>C. albicans</em> was found to be lower in comparison to their activity against bacteria.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 1","pages":"Pages 101-119"},"PeriodicalIF":2.1000,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599323000946","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A series of thiosemicarbazones (TSCs) (L1–5) containing benzothiophen moiety were prepared via the reaction of 3-methyl/3-bromobenzo[b]thiophene-2-carboxaldehyde with appropriate thiosemicarbazides. The compounds were confirmed by elemental analysis, FT-IR, 1H NMR, MALDI-TOF and single crystal X-Ray diffraction techniques. The compounds exist in the E conformation with respect to the azomethine C = N double bond as confirmed by their C8/C9/N1/N2 torsion angles being 178.4(2)° (L1), – 175.2(5)/177.4(5)° (L2), 177.5(2)° (L3), 179.7(3)° (L4), and – 177.4(7)° (L5). These compounds were researched for their antibacterial activity against Gram-positive bacteria (E. faecalis and S. aureus), Gram-negative bacteria (E. coli, P. aeruginosa and S. marcescens) and antifungal activity against a yeast species C. albicans. The ligands possessed varying degrees of antimicrobial activity. Generally, the compounds demonstrated higher efficacy against gram-positive bacteria than gram-negative ones. The antifungal activity of the compounds against C. albicans was found to be lower in comparison to their activity against bacteria.
期刊介绍：
The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science.
Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
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