ArticlesPreparation and Properties of (R)-(−)-1-Azabicyclo[2.2.2]Oct-3-yl-(R)-(+)-α-Hydroxy-α-(4-[125l]Iodophenyl)-α-Phenyl Acetate and (R)-(−)-1-Azabicyclo[2.2.2]Oct-3-Yl-(S)-(−)-α-hydroxy-α-(4-[125l]iodophenyl)-α-phenyl acetate as potential radiopharmaceuticals

Add time:08/16/2019    Source:sciencedirect.com

rac-4-Nitrobenzilic acid was synthesized and resolved with quinidine and quinine to give the corresponding (R)- and (S)-salts. The resolved diastereomeric salts were converted to (R)- and (S)-4-nitrobenzilic acids and subsequent esterification gave their corresponding ethyl esters. Transesterification with (R)-(−)-3-quinuclidinol afforded (R)-(−)-1-azabicyclo[2.2.2]oct-3-yl-(R)-(+)-α-hydroxy-α-(4-nitrophenyl)-α phenyl acetate and (R)-(−)-1-azabicyclo[2.2.2]oct-3-yl-(S)-(−)-α-hydroxy-α-(4-nitrophenyl)-α-phenyl acetate. After hydrogenation, the (R,R)- and (R,S)-amines were converted to the respective triazene derivatives. The triazene derivatives reacted with sodium [125l]iodide to give (R)-(−)-1-azabicyclo[2.2.2]oct-3-yl-(R)-(+)-α-hydroxy-α-(4-[125l]iodophenyl)-α-phenyl acetate and (R)-(−)-1-azabicyclo[2.2.2]oct-3-yl-(S)-(−)-α-hydroxy-α-(4-[125l]iodophenyl)-α-phenyl acetate. The evaluation of their affinities to muscarinic acetylcholine receptors (MAcChR) shows that (R)-(−)-1-azabicyclo[2.2.2]oct-3-yl-(S)-(−)-α-hydroxy-α-(4-[125 I]iodophenyl)-α-phenyl acetate exhibits an affinity for the MAcChR from corpus striatum that is approximately threefold lower than that of (R)-(−)-1-azabicyclo[2.2.2]oct-3-yl-(R)-(+)-α-hydroxy-α-(4-[125l]iodophenyl)-α-phenyl acetate.

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