6 Tyrosine Hydroxylase Inhibitor,Oudenoneおよびその同族体の合成

概要

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In the course of the studies on enzyme inhibitors produced by micro-organisms in our laboratories, oudenone was discovered in a culture filtrate of Oudemansiella radicata in 1970, and it showed inhibition of tyrosine hydroxylase and exhibited significant hypotensive effect. Oudenone is structurally unique, existing as 2-[4,5-dihydro-5-propyl-2(3H)-furylidene]-1,3-cyclopentanedione (1) and 2-(4-hydroxyheptanoyl)-1,3-cyclopentanedione (2b) in solid state or acidic medium and basic solution, respectively. Oudenone has been synthesized by the reaction of 2-acetyl-1,3-cyclopentanedione and furfural followed by hydrogenation over Pt in the presence of 1 mol equiv. of sodium hydroxide and neutralization. 2-[3-(2-Tetrahydrofuryl)propionyl]-1,3-cyclopentanedione (8) has been transformed to 1 by treatment with HI followed by hydrogenation. Oudenone homologues 12, 13, 14, 15, 16, 17, 18, 19, 20 have been synthesized by various methods and their inhibitory activity to tyrosine hydroxylase was investigated. It has been shown that the most important part for the biological activity is attributed to β-trione moiety.
天然有機化合物討論会の論文
1972-10-01