Synthesis of imidazo[1,2-a]pyridines as antiviral agents.
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.
Gueiffier
A
A
Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université de Tours, 31 Avenue Monge, 37200 Tours, France.
Mavel
S
S
Lhassani
M
M
Elhakmaoui
A
A
Snoeck
R
R
Andrei
G
G
Chavignon
O
O
Teulade
J C
JC
Witvrouw
M
M
Balzarini
J
J
De Clercq
E
E
Chapat
J P
JP
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
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