Synthesis and biological evaluation of novel nitrogen- and sulfur-containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents


Ibis C., Tuyun A. F. , Ozsoy-Gunes Z. , Bahar H. , Stasevych M. V. , Musyanovych R. Y. , ...More

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.46, no.12, pp.5861-5867, 2011 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 46 Issue: 12
  • Publication Date: 2011
  • Doi Number: 10.1016/j.ejmech.2011.09.048
  • Title of Journal : EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Page Numbers: pp.5861-5867
  • Keywords: Antibacterial activity, Antifungal activity, 2,3-Dichloro-1,4-naphthoquinone, Amino-sulfinylnaphthoquinone, Quinone, SPECTRAL PROPERTIES, TETRAKIS(THIO)-SUBSTITUTED QUINONES, 1,4-NAPHTHOQUINONE DERIVATIVES, P-CHLORANIL, DESIGN

Abstract

1,4-Naphthoquinones are unique reagents in organic synthesis and have been employed in several well known and recently developed areas of application. Furthermore, these 1,4-naphthoquinones have demonstrated high reactivity in nucleophilic vinylic substitutions, in the preparation of sulfurated, (hetero)cyclic and several other transformations. This study describes the synthesis and biological evaluation of derivatives of monosulfurated naphthalene-1,4-dione (3), 3-chloro-2-ethoxy-naphthalene-1,4-dione (4), disulfurated naphthalene-1,4-dione (5), and symmetrical bis-1,4-naphthoquinones (7, 9) were obtained from the reaction of 2,3-dichloro-naphthaquinone (1) with S-, O-substituted mono-, di-, and tetrathiols, respectively. The structures of the novel products were characterized by spectroscopic methods. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.