Synthesis, chromatography and tissue distribution of 1‐[<sup>11</sup> C]‐hexobarbital

Kloster, G.; Müller‐Platz, C.

doi:10.1002/jlcr.2580180515

Cited by 6 publications

References 4 publications

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Potential cerebral perfusion agents. Synthesis and evaluation of new radioiodinated barbituric acid analogs

Srivastava

Guyer

Knapp

1983

Journal of Heterocyclic Chem

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Two new 125I‐labeled barbituric acid analogs, 5‐ethyl‐5‐(E‐1‐iodo‐1‐penten‐5‐yl)2‐thiobarbituric acid (4) and 5‐ethyl‐5‐(m‐iodophenyl)barbituric acid (7), have been prepared and evaluated in rats as potential cerebral perfusion agents. Annulation of 2‐ethyl‐2‐(E‐1‐iodo‐1‐penten‐5‐yl)malonate (3) with thiourea in the presence of sodium ethoxide gave the 5‐ethyl‐5‐(E‐1‐iodo‐1‐penten‐5‐y1)‐thiobarbituric acid (4). Diethyl 2‐ethyl‐2‐phenyl‐malonate was treated with thallium(III) trifluoroacetate followed by addition of aqueous potassium iodide to provide diethyl 2‐ethyl‐2‐(m‐iodophenyl)malonate (10). The malonic ester derivative 10 was condensed with urea in the presence of sodium hydride to give the desired 5‐ethyl‐5‐(m‐iodophenyl)barbituric acid (7), and a decarbethoxylation product, 2‐(m‐iodophenyl)butyric acid (11). Iodine‐125‐labeled 4 and 7 were synthesized in the same manner and the tissue distribution of these new agents evaluated in rats. Both [125I] 4 and [125I] 7 showed high brain uptake. Significant in vivo deiodination was detected with [125I] 4 whereas [125I] 7 was found to be stable to deiodination.

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