Synthesis and biological activity of 6'-phenylgriseofulvin as analogs of antibiotic griseofulvin

항진균성항생물질 griseofulvin 유도체인 6'-phenylgriseofulvin의 합성과 항균활성

In order to study the influence of a 6'-methyl group in ring C of griseofulvin ${\underline{(1)}}$ on the fungicidal activity, 6'-methyl group was replaced with a larger phenyl group as $({\pm})-6'-phenylgriseofulvin$ ${\underline{(3)}}$, $({\pm})-6'-epiphenylgriseofulvin$ ${\underline{(4)}}$, synthesized by a Diels-Alder cycloaddition. Their biological activities were examined against Botrytis allii (IFO 9430) and B. cinerea (AHU 9573). $({\pm})-6'-Phenylgriseofulvin $ ${\underline{(3)}}$ showed high activity in $25\;{\mu}g/disc$.

Griseofulvin의 구조활성상관연구에서 6'-methyl기와 4'-oxo기가 생물활성에 있어서 중요한 인자라는 것이 예견되어, 6'-methyl기(基)를 phenyl기(基)로 치환한 6'-phenylgriseofulvin을 diels-alder부가환화로 합성하고 Botrytis allii 및 B. cinerea에 대한 항균활성을 paper disc 법으로 연구하였다. 6'-Phenylgriseofulvin은 $25\;{\mu}g/disc$에서 높은 항균활성을 나타냈다.