Development of radioligands for the imaging of cardiac beta-adrenoceptors using SPECT. Part I: Asymmetric synthesis and structural characterization of five new iodine-containing beta-adrenoceptor antagonist derivatives.
The asymmetric synthesis of a series of iodinated beta-adrenoceptor ligands is described. One ligand, (S)-(-)-[1-(2-iodophenoxy)]-3'-(tert-butylamino)-2'-propanol (CYBL3), is based on the beta-adrenoceptor antagonist penbutolol. The other ligands are N-iodovinyl and N-iodoaryl analogues of the beta-adrenoceptor antagonist CGP12177. These have been synthesized from 2-amino-3-nitrophenol. Furthermore, radioiodinated [123I]CYBL3 and [123I](2'S,2"E)-[4-(3'-(1",1"-dimethyl-3"-iodo-2" propenylamino)-2'-hydroxy propoxy)]-benzimidazol-2-one have been prepared by radiolabelling the corresponding trialkyltin precursors using [123I]-NaI in the presence of hydrogen peroxide.
van den Bos
J C
JC
Eindhoven University of Technology, The Netherlands.
van Doremalen
P A
PA
Dubois
E A
EA
Somsen
G A
GA
Vekemans
J A
JA
Janssen
A G
AG
Boer
G J
GJ
Pfaffendorf
M
M
van Royen
E A
EA
van Zwieten
P A
PA
D000319:Adrenergic beta-Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D011412:Propanolamines / Q000737:chemistry; D011869:Radioligand Assay; D015899:Tomography, Emission-Computed, Single-Photon
D000319:Adrenergic beta-Antagonists; D006847:Hydrocarbons, Iodinated; D008024:Ligands; D011412:Propanolamines; C033394:CGP 12177