臺灣博碩士論文加值系統

為了得到強力的抗過敏與抗發炎之新型先導化合物，所以著手
進行 6,7,4'-substituted isoflavanquinone (Ⅶ1∼Ⅶ3) 之合成及其生
物活性之評估。 主要的中間體 6,7,4'-substituted
2'-benzyloxyisoflavone (Ⅴ1∼Ⅴ3) 係由 4,4',5'-substituted
2-benzyloxy-2'-hydroxychalcone (Ⅱ1∼Ⅱ3) 以 thallium(Ⅲ) 及
trimethyl orthoformate 處理，經由氧化性重排而獲得。繼而以 Pd/C
之催化性氫化反應將化合物Ⅴ1∼Ⅴ3 還原成相對應的
6,7,4'-substituted 2'-hydroxyisoflavan (Ⅵ1∼Ⅵ3)。最後利用
Fremy's salt 將 6,7,4'-substituted-2'-hydroxyisoflavan (Ⅵ1∼
Ⅵ3) 氧化成 6,7,4'-substituted isoflavanquinone (Ⅶ1∼Ⅶ3)
將目標化合物 6,7,4'-substituted isoflavanquinone (Ⅶ1∼Ⅶ3)及其
相關化合物進行抗過敏與抗發炎之活性評估，這些化合物中以具有
quinonyl 官能基之衍生物 4'-methoxyisoflavanquinone (Ⅶ1)、7-
methoxyisoflavanquinone (Ⅶ2)、6-fluoroisoflavanquinone (Ⅶ3)
、4'-methoxyisoflavonequinone (Ⅸ1)、7-methoxyisoflavonequinone
(Ⅸ2) 及 6-fluoroisoflavonequinone (Ⅸ3) 為最具潛力之物質，可做
為新型抗血小板、抗發炎及抗過敏藥物之基本架構。

In order to obtain novel lead compounds with potent
antiallergic and anti-inflammatory activities,
6,7,4'-substituted isoflavanquinones were synthesized and
evaluated for bioactivities. 6,7,4'-substituted
2'-benzyloxyisoflavone (Ⅴ1∼Ⅴ3), the key intermediate,was
synthesized through the oxidative rearrangement of
4,4',5'-substituted 2-benzyloxy-2'-hydroxychalcone (Ⅱ1∼Ⅱ3)
with thallium(Ⅲ) nitrate. The product Ⅴ1∼Ⅴ3 was then reduced
by catalytic hydrogenation on Pd/C to the corresponding
6,7,4'-substituted 2'-hydroxy-isoflavan (Ⅵ1∼Ⅵ3) with loss of
the benzyl group. 6,7,4'-Substituted 2'-hydroxyisoflavan (Ⅵ1∼
Ⅵ3) was furtheroxidized with Fremy's salt to give the target
compound 6,7,4'-substituted isoflavanquinone (Ⅶ1∼Ⅶ3). The
target compounds Ⅶ1∼Ⅶ3 and its related compounds were
evaluated for their antiallergic and anti-inflammatory
activities. Among compounds tested, 3-quinonyl derivatives,
namely 4'-methoxy-isoflavanquinone (Ⅶ1),
7-methoxyisoflavanquinone (Ⅶ2), 6-fluoro-isoflavanquinone
(Ⅶ3), 4'-methoxyisoflavonequinone (Ⅸ1), 7-methoxy-
isoflavonequinone (Ⅸ2) and 6-fluoroisoflavonequinone (Ⅸ3) were
the most promising agents, which provide a novel structural
prototype for antiallergic and anti-inflammatory agents.