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.

Synthesis and Antiviral Activities of 3-Aralkyl-Thiomethylimidazo[1,2-b]Pyridazine Derivatives

“…Compounds 8, 9 and 10 showed slight activity against VZV, while compound 12 was inactive. Finally, as previously observed in the imidazo[1,2-a] series (Gueiffier et al, 1998), a phenethylthiomethyl group enhanced the antiviral activity against VZV and CMV in regard to a phenylthiomethyl.…”

Recent strategies in the development of new human cytomegalovirus inhibitors

“…79 SAR studies de®ned the nature of the thioether side chain which must contain an aromatic cyclic ring. 80 The fact that they show selective activity against these two viruses suggests that they are preferentially metabolized by the virus infected cells and/or show particular af®nity for virus-speci®c enzymes.…”

Tin(II) Chloride Dihydrate Catalyzed Groebke Condensation: An Efficient Protocol for the Synthesis of 3‐Aminoimidazo[1,2‐a]pyridines

“…Organic compounds containing the imidazo[1,2-a]-pyridine ring system have been shown to possess a broad range of useful pharmacological activities, including antibacterial, 1 antifungal, 2 anthelmintic, 3 antiviral, 4 antiprotozoal, 5 anti-inflammatory, 6 anticonvulsant, 7 anxiolytic (Alpidem), hypnotic (Zolpidem), 8 antiulcer (Zolmidine), 7 and immunomodulatory (Kifunensine) activities. 9 They have also been shown to be selective cyclin dependant kinase inhibitors, 10 GABA and benzodiazepine receptor antagonists, 11 and bradykinin B 2 receptor antagonists.…”