title: Novel Nucleoside Analogues: First Synthesis of Pyridine-4-Thioglycosides and Their Cytotoxic Evaluation.
abstract: The reaction of sodium 2,2-dicyanoethene-1,1-bis(thiolate) with 2-cyano-N-arylacetamides afforded sodium pyridine-4-thiolates, coupling of the latters with 2,3,4,6-tetra-O-acetyl-D-gluco- and D-galactopyranosyl bromides, respectively, afforded new pyridine-4-thioglycosides. Ammonolysis of the latter compounds afforded the free thioglycosides. The antitumor activities of the synthesized compounds were tested against human tumor cell lines; lung (A549), colon (HCT116), liver (HEPG2), and prostate (PC3).
authors.affiliation: a Chemistry Department, Faculty of Science, Helwan University , Helwan , Cairo , Egypt.
authors.forename: Galal
authors.initials: G
authors.lastname: Elgemeie
authors.affiliation: b Green Chemistry Department, National Research Center , Dokki , Cairo , Egypt.
authors.forename: Mamdouh
authors.initials: M
authors.lastname: Abou-Zeid
authors.affiliation: a Chemistry Department, Faculty of Science, Helwan University , Helwan , Cairo , Egypt.
authors.forename: Shahinaz
authors.initials: S
authors.lastname: Alsaid
authors.affiliation: a Chemistry Department, Faculty of Science, Helwan University , Helwan , Cairo , Egypt.
authors.forename: Ali
authors.initials: A
authors.lastname: Hebishy
authors.affiliation: a Chemistry Department, Faculty of Science, Helwan University , Helwan , Cairo , Egypt.
authors.forename: Hanaa
authors.initials: H
authors.lastname: Essa
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000633:toxicity; D045744:Cell Line, Tumor; D015195:Drug Design; D006801:Humans; D008297:Male; D011725:Pyridines / Q000138:chemical synthesis* / Q000633:toxicity; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000633:toxicity; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000633:toxicity
chemical_list: D000970:Antineoplastic Agents; D011725:Pyridines; D013865:Thioglycosides; D013872:Thionucleosides
keywords: Ketene dithioacetals; activated nitriles; pyridine-4-thioglycosides; sodium pyridine-4-thiolates