Synthesis of Armepavine and Its Derivatives

• Main Authors: Ciou Su Ru, 邱素銣
• Other Authors: 游錫榕
• Format: Others
• Language: zh-TW
• Published: 2006
• Online Access: http://ndltd.ncl.edu.tw/handle/51174186975970128786

碩士 === 中國文化大學 === 應用化學研究所 === 95 === The immune system is a natural defense mechanism in the human body, providing protection against exogenous invasive agents (such as bacteria, virus, and so on), and suppression of growth of cancer cells within the body. Immune deficiency often leads to severe infection and cancer formation, while over-active immune responses can lead to allergy and autoimmune diseases. Evidence from literature suggests that one of the component from the extract of lotus seeds, namely (S)-armepavine, has suppressive effects on plant agglutinin-induced hyperplasia of human peripheral blood monocytes. In addition, (S)-armepavine can inhibit enlargement of lymph nodes. Most of T cells trigger the immune system by the interaction between antigen and T cell receptor on the surface of the membrane. Thus, (S)-armepavine can inhibit proliferation and activation of T-cells. In this thesis, 4-hydroxyphenylacetic acid was used as the starting material to synthesize armepavine, which reacted with 3,4-dimethoxy- phenethylamine after the protection of its hydroxyl group or the benzyl ether, followed by a cyclization reaction to give dihydroisoquinoline. This intermediate was reduced to give tetrahydroisoquinoline, and reacted further to afford armepavine by reductive amination and hydrogenolysis of the benzyl ether. The derivatives of armepavine were also synthesized by the similar method.