Synthesis of analogues of (-)-cytisine for in vivo studies of nicotinic receptors using positron emission tomography.
[formula: see text] 9-Substituted analogues of (-)-cytisine were synthesized in high yields via palladium-mediated couplings of either 9-(-)-bromocytisine and organostannanes or 9-(-)-trimethylstannylcytisine and fluorobromobenzene. The protection of the amine with a nitroso group and the use of PdCl2(PPh3)2 to carry out the Stille reaction allowed the rapid synthesis of 9-(4'-[18F]fluorophenyl)cytisine (18F: t1/2 = 109.7 min), a new promising radioligand (radiochemical yield: 10% from [18F]KF, 150 min, four steps) for positron emission tomography studies of alpha 4 beta 2 nicotinic receptors.
Marrière
E
E
Laboratoire de Chimie Moléculaire et Thio-Organique, UMR CNRS 6507, Institut des Sciences de la Matière et du Rayonnement, Université de Caen-Basse-Normandie, Caen, France.
Rouden
J
J
Tadino
V
V
Lasne
M C
MC
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001392:Azocines; D010165:Palladium / Q000737:chemistry; D011807:Quinolizines; D011978:Receptors, Nicotinic / Q000378:metabolism*; D014055:Tomography, Emission-Computed; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D001392:Azocines; D010165:Palladium; D011807:Quinolizines; D011978:Receptors, Nicotinic; C004712:cytisine; D000093843:Quinolizidine Alkaloids