Synthesis, structure, and binding of some 2-imidazolines to rat brain alfa-1 and alfa-2-adrenergic receptors.
A series of novel 2-[(2-aminophenyl)imino]imidazolinium salts 3a-d and N-benzyl-N-(4,5-dihydro-imidazol-2-yl)-O-methylhydroxylamine hydrochloride 7a-c were prepared and their structure was determined by IR and NMR spectroscopic data as well as X-ray analysis of the imidazolinium azide salt 3e. Binding evaluation for both alpha 1- and alpha 2-adrenergic receptors in rat brain preparations of these compounds and the previously described alpha-hydroxy-2-aryliminoimidazolines 11a-d, N-(4,5-dihydroimidazol-2-yl)-1,3-2-oxodihydrobenzimidazoles 12a-b, 2-amino-N-(4,5-dihydroimidazol-2-yl)-benzimidazoles 13a-b, and N-(4,5-dihydroimidazol-2-yl)-indoles 14a-b was performed. Among the compounds tested, 2-[(2-amino-4,5-dichlorophenyl)imino]imidazolinium chloride 3c showed highest binding affinity to alpha 2-adrenoreceptors (Ki = 30 nM).
Saczewski
F
F
Department of Chemical Technology of Drug and Organic Chemistrys, Medical University of Gdańsk, Poland.
Kobierska
E
E
Debowski
T
T
Charakchiewa-Minol
S
S
Mokrosz
M
M
Gdaniec
M
M
Nowak
E
E
D000818:Animals; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D066298:In Vitro Techniques; D008968:Molecular Conformation; D011869:Radioligand Assay; D051381:Rats; D018340:Receptors, Adrenergic, alpha-1 / Q000378:metabolism*; D018341:Receptors, Adrenergic, alpha-2 / Q000378:metabolism*
D007093:Imidazoles; D018340:Receptors, Adrenergic, alpha-1; D018341:Receptors, Adrenergic, alpha-2