Synthesis and biological evaluation of novel nitrogen- and sulfur-containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents.
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.
Istanbul University, Engineering Faculty, Department of Chemistry, Istanbul, Turkey. ibiscml@istanbul.edu.tr
Cemil
C
Ibis
Amac Fatih
AF
Tuyun
Zeliha
Z
Ozsoy-Gunes
Hakan
H
Bahar
Maryna V
MV
Stasevych
Rostyslav Ya
RY
Musyanovych
Olena
O
Komarovska-Porokhnyavets
Volodymyr
V
Novikov
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D001424:Bacterial Infections / Q000188:drug therapy; D005658:Fungi / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D009181:Mycoses / Q000188:drug therapy; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009584:Nitrogen / Q000737:chemistry / Q000494:pharmacology; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D009285:Naphthoquinones; D013457:Sulfur Compounds; D009584:Nitrogen