[Azoles. 27. Nitroimidazole derivatives, their antibacterial and fungicidal activity and electron affinity]

Pharmazie. 1989 Dec;44(12):817-20.
[Article in German]

Abstract

Nitroimidazole derivatives 3a-3g, 4a-4g and 5-8 were synthesized by treating 4,5-dinitro- and 2-methyl-4,5-dinitroimidazole (1,2) with phenacyl bromide, its p-substituted derivatives or epichlorohydrin. 1-(3-Chloro-2-hydroxypropyl)-4,5-dinitroimidazole (5) and its 2-methyl derivative 6 have been converted to imidazo-oxazoles 7 and 8 or amino imidazole derivatives 9-14 by the action of potassium carbonate or cyclic amines (pyrrolidine, piperidine, morpholine and N-methylpiperazine). Some of the newly synthesized nitroimidazole derivatives show antibacterial and fungicidal activity. The electron affinity of the nitroimidazole derivatives 1-24 is discussed on the basis of their half-wave potentials and in the connection with their eventual radiosensitizing properties.

MeSH terms

  • Anti-Bacterial Agents
  • Anti-Infective Agents / chemical synthesis*
  • Antifungal Agents / chemical synthesis*
  • Azoles / chemical synthesis*
  • Azoles / pharmacology
  • Bacteria / drug effects
  • Chemical Phenomena
  • Chemistry, Physical
  • Electrons
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Nitroimidazoles / chemical synthesis*
  • Nitroimidazoles / pharmacology

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Azoles
  • Nitroimidazoles