31.ジャスモン酸生合成阻害剤JM-8686の不斉合成と生物活性(口頭発表)

概要

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The preparation of both enantiomers of 8-[1-(2, 4-dichlorophenyl)-2-imidazol-1-yl-ethoxy] octanoic acid heptyl ester (JM-8686), a potent inhibitor of allene oxide synthase, has been achieved from 2, 4-dichlorophenacyl bromide as a starting material. The key step was the asymmetric reduction of 1-(2, 4-dichlorophenyl)-2-imidazol-1-yl-ethanone. The synthesized optical active (R)-(-)-JM-8686 and (S)-(+)-JM-8686 were purified by chiral HPLC. The inhibitory activities and binding affinities of these enantiomers against allene oxide synthase were determined. We found that the inhibition potency of the (R)-(-)-JM-8686 was approximate 200 times to that of (S)-(+)-JM-8686, with an IC_<50> value approximate 5 ± 0.2 nM and 950 ±18 nM, respectively. The spectral dissociation contents of (R)-(-)-JM-8686 and (S)-(+)-JM-8686 to the recombinant allene oxide synthase were approximate 1.4 ± 0.3 μM and 4.8 ± 0.6 μM, respectively.
植物化学調節学会の論文
2007-10-05