Isomeric phenylthioimidazo[1,2-alpha]pyridines as anthelmintics

J Med Chem. 1981 Dec;24(12):1483-7. doi: 10.1021/jm00144a022.

Abstract

A series of isomeric imidazo[1,2-alpha]pyridine-2-carbamates was prepared for testing as anthelmintics. The analogues were synthesized by reacting the appropriate 2-aminopyridine and methyl chloroacetylcarbamate. Steric hindrance in the 2,6-disubstituted derivative resulted in the formation of the isomeric 3-substituted analogue as the major product. Carbon-13 NMR proved useful in the structural assignments in this series. None of the analogues exhibited the potency of methyl 6-(phenylsulfinyl)imidazo[1,2-alpha]pyridine-2-carbamate when tested against Nematospiroides dubius in mice.

MeSH terms

  • Animals
  • Anthelmintics / chemical synthesis*
  • Carbamates / chemical synthesis
  • Carbamates / pharmacology
  • Chemical Phenomena
  • Chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology
  • Isomerism
  • Mice
  • Nematode Infections / drug therapy

Substances

  • Anthelmintics
  • Carbamates
  • Imidazoles