Molecules (Nov 2018)

Synthesis of Carvone-Derived 1,2,3-Triazoles Study of Their Antioxidant Properties and Interaction with Bovine Serum Albumin

  • Armen S. Galstyan,
  • Armen I. Martiryan,
  • Karine R. Grigoryan,
  • Armine G. Ghazaryan,
  • Melanya A. Samvelyan,
  • Tariel V. Ghochikyan,
  • Valentine G. Nenajdenko

DOI
https://doi.org/10.3390/molecules23112991
Journal volume & issue
Vol. 23, no. 11
p. 2991

Abstract

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Natural L-carvone was utilized as a starting material for an efficient synthesis of some terpenyl-derived 1,2,3-triazoles. Chlorination of carvone, followed by nucleophilic substitution with sodium azide resulted in the preparation of 10-azidocarvone. Subsequent CuAAC click reaction with propargylated derivatives provided an efficient synthetic route to a set of terpenyl-derived conjugates with increased solubility in water. All investigated compounds exhibit high antioxidant activity, which is comparable with that of vitamin C. It was also found that serum albumin and the terpenyl-1,2,3-triazoles hybrids spontaneously undergo reversible binding driven by hydrophobic interactions, suggesting that serum albumin can transport the target triazoles.

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