| Summary: | 碩士 === 台北醫學院 === 藥學研究所 === 81 === Cafeetannins 及 polyphenolic caffeoylquinic acid 之衍生物,其廣泛
分佈於植物中,其中一種活性成分methyl 3,4-dicaffeoyl- quinate被發
現具強烈的抑制血小板凝集作用和抑制人類血小板throm- boxane之生合
成.為了評估其化學構造與血小板凝集及 thromboxane 之生成抑制作用關
係,擬以 methyl 3,4-dicaffeoylquinate 為化學合成目標, 製備多種類
似化合物.我們利用 cinnamic acid, 3,4-dimethoxycinnamic acid,
3,4- methylenedioxycinnamic acid and caffeic acid 之 acyl
chlorides 和一系列 aliphatic alcohols 和 phenolic alcohols 反應
而得 22 種產物. 1,3-dicinnamoylpropanediol (1), 1,3-di(3',4'-
dimethoxy- cinnamoyl)propanediol (2), 1,3-di(3',4'-
methlenedioxycinnamoyl) propanediol (3),
1,2-dicinnamoylpropanediol (4), 1,2-di(3',4'-
dimethoxycinnamoyl)propanediol (5), 1,2-di(3',4'-
methylenedioxy- cinnamoyl)propanediol (6),
1,2-dicinnamolcyclohexanediol (7), 1,2-di(3',4'-
dimethoxycinnamoyl)cyclohexanediol (8), 1,2-di(3',
4'-methylenedioxycinnamoyl)cyclohexanediol (9),
1,2-dicinnamoyl- glycerol (10), 1,2-di(3',4'-dimethoxycinnamoyl)
glycerol (12), methyl 3,4-dicinnamoylbenzoate (13),methyl
3,4-di(3',4'-methoxy- cinnamoyl)benzoate (14), methyl
3,4-di(3',4'-methylenedioxycin- namoyl)benzoate (15), methyl
3,4,5-tricinnamoylgallate (16), methyl 3,4,5-tri(3',4'-
dimethoxycinnamoyl)gallate (17), methyl 3,4,5-tri(3',4'-
methylenedioxycinnamoyl)gallate (18), methyl 3,4-dicinnamoyl-5-
methoxybenzoate (19), methyl 3,4-di-(3',4'-
dimethoxycinnamoyl)-5-methoxybenzoate (20), methyl
3,4-di(3',4'- methylenedioxycinnamoyl)-5-methoxybenzoate (21),
1,3-dicaffeoyl- propanediol (22).此 22 種目的化合物經紅外光譜,
氫譜, 碳譜及質譜光譜分析確定其化學結構, 其有關血小板凝集抑制之藥
理作用正在試驗中.
Cafeetannins are naturaly occurring polyphenolic caffeoyl-
quinic acid derivatives.One of these compounds, methyl 3,4-dic-
affeoylquinate,was found to be inhibitory toward platelet aggr-
egation and thromboxane biosynthesis on human platelet.
Therefore, several analoques modeled after methyl
3,4-dicaffeoylquinate were prepared by chemical synthesis in
order to evaluate the relationship between their structures and
antiplatelet and the thromboxane formation inhibitory activity.
The acyl chloride derivatives of the substituted cinnamic
acids, were reacted with a series dihydroxyl or trihydroxyl
compounds of alcohols and phenols to yield 22 cinnamic acid
esters. They are 1,3-dicinnamoylpropanediols (1),(2) and (3) ,
1,2-dicinnamoylpropanediols (4),(5) and (6),1,2-dicinnamoyl-
cyclohexanediols (7),(8) and (9),1,2-dicinnamoylglycerol (10),
(11) and (12),methyl 3,4-dicinnamoylbenzoates (13),(14) and
(15) , methyl 3,4,5-tricinnamoylgallates (16),(17) and (18),
methyl 3,4-dicinnamoyl-5-methoxybenzoates (19),(20) and (21),
1,3-dicaffeoylpropanediol (22). The structures of these 22
compounds are consistant with the spectral data (UV, IR, PMR,
CMR and Mass). The evaluation of platelet aggregation
inhibitory activity is under investi- gated.
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