title: One-pot synthesis of 5-phenylimino, 5-thieno or 5-oxo-1,2,3-dithiazoles and evaluation of their antimicrobial and antitumor activity.
abstract: We here report the synthesis and biological evaluation of rare 4-substituted-5-phenylimino, 5-thieno- and 5-oxo-1,2,3-dithiazoles. Dithiazoles were selectively obtained in moderate to high yields (25-73%) via a one-pot reaction from various ethanoneoximes with sulfur monochloride, pyridine in acetonitrile followed by treatment by corresponding nucleophiles (aniline, thioacetamide and formic acid). All the synthesized compounds were screened for their antibacterial (against bacteria Escherichia coli, Salmonellaenterica serovar Typhimurium, Klebsiella pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Bacillus cereus and Listeria inocua), antifungal (against pathogenic strains Candida albicans, Candida glabrata, Candida tropicalis and Issatchenkia orientalis) and antitumor (on human cell lines MCF-7 and MDA-MB-231) activity. 4-(2-Pyridinyl)-5H-1,2,3-dithiazole-5-thione and 4-ethylcarboxyl-5H-1,2,3-dithiazole-5-thione (5d, 5h) that are active against Gram-positive bacteria are significantly active against fungi. 4-(2-Benzofuranyl)-5-phenylimino-5H-1,2,3-dithiazole (4e) exerts antiproliferative activity.
authors.affiliation: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
authors.forename: Lidia S
authors.initials: LS
authors.lastname: Konstantinova
authors.forename: Oleg I
authors.initials: OI
authors.lastname: Bol'shakov
authors.forename: Natalia V
authors.initials: NV
authors.lastname: Obruchnikova
authors.forename: Hélène
authors.initials: H
authors.lastname: Laborie
authors.forename: Annabelle
authors.initials: A
authors.lastname: Tanga
authors.forename: Valérie
authors.initials: V
authors.lastname: Sopéna
authors.forename: Isabelle
authors.initials: I
authors.lastname: Lanneluc
authors.forename: Laurent
authors.initials: L
authors.lastname: Picot
authors.forename: Sophie
authors.initials: S
authors.lastname: Sablé
authors.forename: Valérie
authors.initials: V
authors.lastname: Thiéry
authors.forename: Oleg A
authors.initials: OA
authors.lastname: Rakitin
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D006801:Humans; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D013844:Thiazoles