title: Influence of 6 or 8-substitution on the antiviral activity of 3-phenethylthiomethylimidazo[1,2-a]pyridine against human cytomegalovirus (HCMV) and varicella-zoster virus (VZV).
abstract: The synthesis of original imidazo[1,2-a]pyridines bearing a phenethylthiomethyl side chain at the 3 position and a (hetero)aryl substituent on the 6 or 8 position, and their antiviral activities are reported. From the synthesized compounds, the 6-halogeno and 6-phenylimidazo[1,2-a]pyridine derivatives 4c-d and 5b were the most potent against human cytomegalovirus (CMV) and/or varicella-zoster virus (VZV), whereas several other congeners (i.e., 5e, 5g, 5i, 5l, 5n, 5p, 5q, and 5t), while less potent, were equally or more selective in their inhibitory activity against both VZV and CMV. These compounds showed similar activity against thymidine kinase competent (TK(+)) and deficient (TK(-)) VZV strains, demonstrating a mechanism of action independent of the viral thymidine kinase.
authors.affiliation: Laboratoire de chimie thérapeutique, Faculté de pharmacie, EA 3857, 31 avenue Monge, 37200 Tours, France.
authors.forename: Jean-Baptiste
authors.initials: JB
authors.lastname: Véron
authors.forename: Cécile
authors.initials: C
authors.lastname: Enguehard-Gueiffier
authors.forename: Robert
authors.initials: R
authors.lastname: Snoeck
authors.forename: Graciela
authors.initials: G
authors.lastname: Andrei
authors.forename: Erik
authors.initials: E
authors.lastname: De Clercq
authors.forename: Alain
authors.initials: A
authors.lastname: Gueiffier
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003587:Cytomegalovirus / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D014645:Herpesvirus 3, Human / Q000187:drug effects*; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C525717:3-phenethylthiomethylimidazo(1,2-a)pyridine; D000998:Antiviral Agents; D007093:Imidazoles; D011725:Pyridines