Bulletin of the Korean Chemical Society

  • 제32권1호
  • /
  • Pages.229-238
  • /
  • 2011
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of Novel D-Glucose-derived Benzyl and Alkyl 1,2,3-Triazoles as Potential Antifungal and Antibacterial Agents

  • Wei, Jin-Jian (Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University) ;
  • Jin, Lei (School of Pharmaceutical Sciences, Southwest University) ;
  • Wan, Kun (Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University) ;
  • Zhou, Cheng-He (Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University)
  • 투고 : 2010.05.17
  • 심사 : 2010.11.15
  • 발행 : 2011.01.20
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초록

A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, $^1H$-$^1H$ and $^1H-^{13}C$ 2D NMR spectra for some compounds were also recorded. These compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis, Bacillus proteus, Pseudomonas aeruginosa, Escherichia coli ATCC 25922, and antifungal activities against Candida albicans and Aspergillus fumigatus. The bioactive data revealed that (3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis((1-octyl-1H-1,2,3-triazol-4-yl)methoxy)-tetrahydro-2H-pyran-3-ol 8a exhibited excellent antifungal activity against A. fumigatus with an MIC value of 0.055 mM compared to Fluconazole. It also showed broad inhibitory efficacy against tested bacterial strains with MIC values ranging from 0.049 mM to 0.39 mM.

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