Preparation, structure and affinity for imidazoline I2 receptors and alpha2-adrenoceptors of 1-[(4,5-dihydroimidazolidin-2-yl)imino]indan-2-ols.
Two enantiomers IR, 2S-(+)-cis (3a) and IS, 2R-(-)-cis (3b) of 1-[(4,5-dihydroimidazolidin-2-yl)imino]indan-2-ol were prepared by reacting 2-chloro-4,5-dihydroimidazole (1) with corresponding 1-amino-indan-2-ols (2a-b). The compounds obtained are structural analogues of PMS 952 agent containing imino bridge in place of methylene group. Compound 3a exhibited moderate almost equal activity at both imidazoline I2 receptors and alpha2-adrenoceptors, while enantiomer 3b was found to be selective for alpha2-adrenoceptors (alpha2/I2 selectivity ratio = 10.4).
Department of Chemical Technology of Drugs, Medical University of Gdańsk, 107 Gen. J. Hallera AV., 80-416 Gdańsk, Poland. a.kornicka@amg.gda.pl
Anita
A
Kornicka
Franciszek
F
Saczewski
Robin J
RJ
Tyacke
Alan L
AL
Hudson
David J
DJ
Nutt
D000818:Animals; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D054755:Imidazoline Receptors; D007189:Indans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D051381:Rats; D017208:Rats, Wistar; D018341:Receptors, Adrenergic, alpha-2 / Q000378:metabolism*; D011955:Receptors, Drug / Q000378:metabolism*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C418770:1-(4',5'-dihydro-1'H-imidazol-2'-yl)methyl-2-hydroxyindane; D007093:Imidazoles; D054755:Imidazoline Receptors; D007189:Indans; D018341:Receptors, Adrenergic, alpha-2; D011955:Receptors, Drug; C487767:imidazoline receptor 2