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

J C van den Bos; P A van Doremalen; E A Dubois; G A Somsen; J A Vekemans; A G Janssen; G J Boer; M Pfaffendorf; E A van Royen; P A van Zwieten

doi:10.1016/s0969-8051(96)00154-0

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

Nucl Med Biol. 1997 Jan;24(1):1-7. doi: 10.1016/s0969-8051(96)00154-0.

Authors

J C van den Bos¹, P A van Doremalen, E A Dubois, G A Somsen, J A Vekemans, A G Janssen, G J Boer, M Pfaffendorf, E A van Royen, P A van Zwieten

Affiliation

¹ Eindhoven University of Technology, The Netherlands.

PMID: 9080468
DOI: 10.1016/s0969-8051(96)00154-0

Abstract

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.

MeSH terms

Adrenergic beta-Antagonists / chemical synthesis*
Adrenergic beta-Antagonists / chemistry
Hydrocarbons, Iodinated / chemical synthesis*
Hydrocarbons, Iodinated / chemistry
Ligands
Molecular Structure
Propanolamines / chemistry
Radioligand Assay
Tomography, Emission-Computed, Single-Photon

Substances

Adrenergic beta-Antagonists
Hydrocarbons, Iodinated
Ligands
Propanolamines
CGP 12177