title: Synthesis of imidazo[1,2-a]pyridines as antiviral agents.
abstract: The synthesis of original imidazo[1,2-a]pyridines bearing a thioether side chain at the 3 position and their antiviral activity are reported. From the synthesized compounds, 4, 15, and 21 were highly active against human cytomegalovirus with a therapeutic index superior to 150. These compounds also showed pronounced activity against varicella-zoster virus. Their structure-activity relationship is discussed.
authors.affiliation: Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université de Tours, 31 Avenue Monge, 37200 Tours, France.
authors.forename: A
authors.initials: A
authors.lastname: Gueiffier
authors.forename: S
authors.initials: S
authors.lastname: Mavel
authors.forename: M
authors.initials: M
authors.lastname: Lhassani
authors.forename: A
authors.initials: A
authors.lastname: Elhakmaoui
authors.forename: R
authors.initials: R
authors.lastname: Snoeck
authors.forename: G
authors.initials: G
authors.lastname: Andrei
authors.forename: O
authors.initials: O
authors.lastname: Chavignon
authors.forename: J C
authors.initials: JC
authors.lastname: Teulade
authors.forename: M
authors.initials: M
authors.lastname: Witvrouw
authors.forename: J
authors.initials: J
authors.lastname: Balzarini
authors.forename: E
authors.initials: E
authors.lastname: De Clercq
authors.forename: J P
authors.initials: JP
authors.lastname: Chapat
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002522:Chlorocebus aethiops; D003587:Cytomegalovirus / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D006367:HeLa Cells; D014645:Herpesvirus 3, Human / Q000187:drug effects; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014709:Vero Cells
chemical_list: C116290:2-methyl-3-((phenylethyl)thiomethyl)imidazo(1,2-a)pyridine; C116291:6-bromo-8-methyl-3-((phenylethyl)thiomethyl)imidazo(1,2-a)pyridine; C116289:7-methyl-3-((phenylethyl)thiomethyl)imidazo(1,2-a)pyridine; D000998:Antiviral Agents; D007093:Imidazoles; D011725:Pyridines