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., ...Daha Fazla

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.46, sa.12, ss.5861-5867, 2011 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 46 Sayı: 12
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1016/j.ejmech.2011.09.048
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5861-5867
  • Anahtar Kelimeler: 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
  • İstanbul Üniversitesi Adresli: Evet

Özet

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.