MAGNETIC SILICA NANOPARTICLE-SUPPORTED COPPER COMPLEX AS AN EFFICIENT CATALYST FOR THE SYNTHESIS OF NOVEL TRIAZOLOPYRAZINYLACETAMIDES WITH IMPROVED ANTIBACTERIAL ACTIVITY

Authors

  • Mohammad Sadegh Asgari School of Chemistry, College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran
  • Saghi Sepehri Department of Medicinal Chemistry, School of Pharmacy, Ardabil University of Medical Sciences, Ardabil, 5618953141, Iran
  • Saeed Bahadorikhalili School of Chemistry, College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran
  • Parviz Rashidi Ranjbar School of Chemistry, College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran
  • Rahmatollah Rahimi Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran 16846-13114, Iran
  • Ahmad Gholami Pharmaceutical Science Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  • Aboozar Kazemi Pharmaceutical Science Research Center, Shiraz University of Medical Sciences, Shiraz, Iran Department of Pharmaceutical Biotechnology, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
  • Mehdi Khoshneviszadeh Pharmaceutical Science Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  • Bagher Larijani Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Research Institute, Tehran University of Medical Sciences, Tehran, Iran
  • Mohammad Mahdavi Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Research Institute, Tehran University of Medical Sciences, Tehran, Iran

DOI:

https://doi.org/10.1007/5388

Keywords:

nanoparticle-supported copper catalyst, triazole, antibacterial agents, click reaction, structure–activity relationship.

Abstract

A novel superparamagnetic iron oxide modified with copper via 2-aminobenzamide is synthesized by the modification of Fe3O4@SiO2
with amine, followed by the reaction with isatoic anhydride. The catalyst is fully characterized by various methods. The catalytic activity of the catalyst is evaluated in the synthesis of a series of novel N-alkyl-2-aryl-2-(6-oxo-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazin-5(4H)-yl)acetamide analogs. Antibacterial activity of the synthesized compounds is evaluated. The catalyst is recoverable and shows excellent reusability in 10 sequential runs.

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Published

2020-04-30

Issue

Vol. 56 No. 4 (2020): Green chemistry of heterocycles

Section

Original Papers