莫若莹, 邵国贤, 朱丽莲, 贺文义. 阿魏酸衍生物的合成J. 药学学报, 1985, 20(8): 584-591.
引用本文: 莫若莹, 邵国贤, 朱丽莲, 贺文义. 阿魏酸衍生物的合成J. 药学学报, 1985, 20(8): 584-591.
MO Ruo-Ying, SHAO Guo-Xian, ZHU Li-Lian , HE Wen-Yi, . SYNTHESIS OF DERIVATIVES OF FERULIC ACIDJ. Acta Pharmaceutica Sinica, 1985, 20(8): 584-591.
Citation: MO Ruo-Ying, SHAO Guo-Xian, ZHU Li-Lian , HE Wen-Yi, . SYNTHESIS OF DERIVATIVES OF FERULIC ACIDJ. Acta Pharmaceutica Sinica, 1985, 20(8): 584-591.

阿魏酸衍生物的合成

SYNTHESIS OF DERIVATIVES OF FERULIC ACID

  • 摘要: 本文报道3种类型18个阿魏酸衍生物的化学合成:Ⅰ.氨基醇酯类化合物,Ⅱ.5-(烷胺基)一次甲基阿魏酸,Ⅲ.双分子阿魏酸的醚类化合物。药理筛选的初步结果表明:Ⅰ类化合物的体外抗凝作用比阿魏酸本身为强,Ⅱ类化合物作用很弱。

     

    Abstract: Ferulie acid is an ingredient of "Dang-Gui" (Angelica sinensis (Oliv.) Diels) and "Chuan Xiong" (Ligusticum wellichit Franch) which had been used for the treatment of thrombotic diseases in traditional Chinese medicine. Three types of derivatives related to ferulie acid have been synthesized. They are alkamine esters of ferulie acid (compounds Ⅰ1~9), 5-amino-methyl ferulic acids (compounds Ⅱ5~8) and bisferulie acid ethers (compounds Ⅲ6~9).Compounds (Ⅰ1~6) were synthesized from 4-0-carbethoxy-ferulie acids by treatment with thionyl chloride to give acid chlorides which were esterified with various amino-alcohols.Compounds (Ⅰ7~9) were obtained by treatment of compounds (Ⅰ1,3,4) with aminoethanol.Compounds (Ⅱ5~8) were prepared from vanillin which underwent Mannich Reaction to provide the intermediates, 5-substituted-amino-methyl-4-hydroxy-3-methoxybenzaldehydes, followed by condensation with malonie acid in pyridine to yield various 5-substituted-amino-methyl-ferulic acids.Vanillin was reacted with dibromopropane-(1,3), dibromohexane-(1,6) or xylylene bromide to form the corresponding ethers.Compounds Ⅲ1~4 underwent Knoevenagel Reaction to form derivatives of bisferulie acid ether (Ⅲ6~8). Vanillin was treated with 3-chloro-1,2-epoxypropane in dilute sodium hydroxide solution to form bis-vanillin-glycerin ether (Ⅲ4) which reacted with malonic acid in pyridine to afford bisferulie acid-glycerin ether (Ⅲ9).Preliminary pharmacological results showed that compounds in the (Ⅰ)series inhibited rat platelet aggregation in vitro at concentration much lower than that of ferulie acid itself.

     

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