New vitamin K3 (menadione) analogues: synthesis, characterization, antioxidant and catalase inhibition activities

DENİZ N. G. , Abdassalam A. F. S. , ÖZYÜREK M. , Yesil E. A. , Sayil C.

Journal of Chemical Sciences, cilt.132, sa.1, 2020 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 132 Konu: 1
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1007/s12039-020-01835-9
  • Dergi Adı: Journal of Chemical Sciences


© 2020, Indian Academy of Sciences.Abstract: In this study, derivatives of new vitamin K3 were synthesized by the reactions of 2-methyl-1,4-naphthoquinone 1 with some heterocyclic ring substituted nucleophiles: 1-piperonylpiperazine 2, 1-(2-furoyl)piperazine 5, 1-(2-aminoethyl)piperidine 8, 1-(2-aminoethyl)pyrrolidine 10 and 2,6-dimethyl morpholine 12 in chloroform/triethylamine (TEA) or ethanol at room temperature. Their structures were characterized by Fourier transform infrared spectroscopy (FT-IR), 1H nuclear magnetic resonance (1H NMR), attached proton test nuclear magnetic resonance (APT-NMR) and mass spectrometry (MS). Newly synthesized vitamin K3 derivatives (3, 4, 6, 7, 9, 11, 13, 14) have shown catalase inhibition activity and compound 13 has displayed remarkable potency against catalase enzyme. These compounds were also tested for their antioxidant capacity in vitro by CUPRAC method. Graphic abstract: New vitamin K3 (menadione) analogues.[Figure not available: see fulltext.]