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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 6, pp 630–637 | Cite as

Design, synthesis, and biological evaluation of new 1-aryl-4-(β-D-fructopyranos-3-O-yl)methyl-1H-1,2,3-triazole derivatives

  • Dinesh Kumar Reddy Vennam
  • Ranjith Kumar Thatipamula
  • Sharath Babu Haridasyam
  • Shiva Kumar Koppula
Article

New 1-aryl-4-(β-D-fructopyranos-3-O-yl)methyl-1H-1,2,3-triazole derivatives have been synthesized by a CuAAC reaction and their antibacterial and antifungal activity has been evaluated. Some of the derivatives showed remarkable in vitro antibacterial activity against Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, and Klebsiella pneumoniae and moderate antifungal activity. In addition, molecular docking studies of these compounds into the active site of Staphylococcus aureus tyrosyl-tRNA synthetase were performed. The docking study revealed that all compounds have considerable binding energies and good affinity toward the active site of the enzyme.

Keywords

arylazide 1-aryl-4-(β-D-fructopyranos-3-O-yl)methyl-1H-1,2,3-triazoles 3-O-propargyl-β-D-fructopyranose antibacterial activity antifungal activity click chemistry molecular docking simulation 

Notes

This work was funded by the University Grants Comission, New Delhi (MRP-Major-chem-2013-21956, 01.07.2015).

Authors thank Department of Chemistry, GITAM Deemed to be University for providing lab facilities; Althaf Hussain, Department of Biotechnology, Kakatiya University, for supporting biological evaluation; Prof. G. A. Ramarao and Dr. G. Rambabu, Department of Chemistry, GITAM Deemed to be University for the valuable suggestions.

Supplementary material

10593_2018_2319_MOESM1_ESM.pdf (21.7 mb)
ESM 1 (PDF 22251 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Dinesh Kumar Reddy Vennam
    • 1
  • Ranjith Kumar Thatipamula
    • 1
  • Sharath Babu Haridasyam
    • 1
  • Shiva Kumar Koppula
    • 1
  1. 1.Department of ChemistryGITAM Deemed to be UniversitySangareddyIndia

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