Synthesis, characterization and anti-microbiological evaluation of 2-[(2,6-diaryl piperidin-4-yl)hydrazono]-2,3-dihydrothiazoles as a new class of antimicrobial agents
{"title":"Synthesis, characterization and anti-microbiological evaluation of 2-[(2,6-diaryl piperidin-4-yl)hydrazono]-2,3-dihydrothiazoles as a new class of antimicrobial agents","authors":"N. Sarathi, S. L. Ashok Kumar, C. Sankar","doi":"10.1007/s13738-024-03090-y","DOIUrl":null,"url":null,"abstract":"<div><p>A series of 2-[(2,6-diarylpiperidin-4-yl)hydrazono]-2,3-dihydrothiazoles (<b>25–40</b>) were synthesized by the reaction of respective thiosemicarbazones (<b>9–24</b>) with phenacyl bromide in the presence of sodium acetate-acetic acid buffer and refluxing in ethanol for 12–16 h. The newly synthesized target compounds were characterized by elemental analysis, mass, FT-IR, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopic methods. A Structure activity relationship study was carried out for the title compounds against a panel of bacterial strains viz<i> Staphylococcus aureus</i>, <i>Escherichia coli</i>, <i>Pseudomonas aeruginosa</i>, <i>Salmonella typhi, Bacillus subtilis</i> and <i>Klebsiella pneumonia</i> and the fungal strains <i>Cryptococcus neoformans</i>, <i>Candida albicans</i>, <i>Rhizopus sp, Aspergillus niger and Aspergillus flavus</i>, respectively, using ciprofloxacin and amphotericin-B as standard drugs. These studies proved that compounds <b>26</b> and <b>34</b> against <i>Staphylococcus aureus</i>, <b>35</b> against <i>P. aeruginosa,</i> <b>38</b> against <i>B. subtilis</i>, and <b>27</b> against <i>K. pneumonia</i> showed maximum inhibitory potency at the lowest concentration (6.25 µg/mL), whereas <b>26</b>, <b>34</b> and <b>35</b> against <i>C. neoformans</i> and <b>26</b> and <b>27</b> against <i>Candida albicans</i> showed beneficial antifungal activity at a minimum concentration (MIC) of 6.25 µg/mL.</p></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-024-03090-y","RegionNum":4,"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 2-[(2,6-diarylpiperidin-4-yl)hydrazono]-2,3-dihydrothiazoles (25–40) were synthesized by the reaction of respective thiosemicarbazones (9–24) with phenacyl bromide in the presence of sodium acetate-acetic acid buffer and refluxing in ethanol for 12–16 h. The newly synthesized target compounds were characterized by elemental analysis, mass, FT-IR, 1H and 13C NMR spectroscopic methods. A Structure activity relationship study was carried out for the title compounds against a panel of bacterial strains viz Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Bacillus subtilis and Klebsiella pneumonia and the fungal strains Cryptococcus neoformans, Candida albicans, Rhizopus sp, Aspergillus niger and Aspergillus flavus, respectively, using ciprofloxacin and amphotericin-B as standard drugs. These studies proved that compounds 26 and 34 against Staphylococcus aureus, 35 against P. aeruginosa,38 against B. subtilis, and 27 against K. pneumonia showed maximum inhibitory potency at the lowest concentration (6.25 µg/mL), whereas 26, 34 and 35 against C. neoformans and 26 and 27 against Candida albicans showed beneficial antifungal activity at a minimum concentration (MIC) of 6.25 µg/mL.
期刊介绍:
JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.