One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study


DENİZ N. G. , ÖZYÜREK M. , TUFAN A. N. , APAK M. R.

MONATSHEFTE FUR CHEMIE, cilt.146, ss.2117-2126, 2015 (SCI İndekslerine Giren Dergi)

  • Cilt numarası: 146 Konu: 12
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1007/s00706-015-1517-5
  • Dergi Adı: MONATSHEFTE FUR CHEMIE
  • Sayfa Sayısı: ss.2117-2126

Özet

In the present study, we reported the one-pot synthesis of S,S- and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur- and oxygen-containing nucleophiles were investigated to obtain highly functionalized S,S- and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of H-1, F-19, and C-13 nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient.