Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes

Novel 1-R-imidazole-5-amidoximes and 1-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observin...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2006-09, Vol.41 (9), p.1073-1079
Main Authors: Oresmaa, L., Kotikoski, H., Haukka, M., Oksala, O., Pohjala, E., Vapaatalo, H., Moilanen, E., Vainiotalo, P., Aulaskari, P.
Format: Article
Language:English
Subjects:
Amidoxime
Amination
Animals
Biological and medical sciences
Cyclic GMP
Cyclic GMP - blood
Eye
Eye - drug effects
Eye - metabolism
Female
Imidazole
Imidazoles - chemistry
Intraocular pressure
Isomerism
Male
Medical sciences
Molecular Structure
Nitrates - chemistry
Nitric oxide
Nitric Oxide - metabolism
Oximes - chemical synthesis
Oximes - chemistry
Oximes - pharmacology
Pharmacology. Drug treatments
Rabbits
Structure-Activity Relationship
Swine
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Summary:Novel 1-R-imidazole-5-amidoximes and 1-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observing the stimulation of formation of cyclic guanosine-3′,5′-monophosphate (cGMP) in the incubation of porcine iris-ciliary body. In the incubation experiments, 1-methylimidazole-5-amidoxime and 1( H)-imidazole-4(5)-amidoxime stimulated formation of cGMP indicating NO donating ability of these compounds. 1-Methylimidazole-5-amidoxime lowered IOP significantly after intravitreal injection.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2006.05.001