含氟修饰的姜黄素衍生物的设计及合成
毕业论文关键词：α-氨基酸；对氟苯甲酸；姜黄素；酯化反应；脂分解反应；L-苯丙氨酸；L-缬氨酸
Design and synthesis of the fluorine modified curcumin derivatives
Abstracts：Taking α-amino acid as raw material, the esterification reaction between α-amino acid and methanol generate Ester compounds to protect the carboxyl. Then the Ester compounds respond to 4-Fluorobenzoic acid and generate amide compounds. The ester decomposition reaction of the amide compound in alkaline environment release the carboxyl, generate carboxylic compounds containing fluorine atom. Finally, the esterification reaction between the fluorine modified carboxylic compound and curcumin generate the fluorine modified curcumin derivatives. This experiment take L - phenylalanine and L - valine as raw material through methanol esterification, amidation reaction, ester decomposition reaction and esterification reaction generate two kinds of target compounds, include single instead of curcumin derivatives and double instead of curcumin derivatives. Because it is difficult to isolate pure target compounds from the mixture compounds, only a small amount of double instead of the target compounds were isolated. The target compounds’ structure is characterized by IR and 1H-NMR.
Keywords：α-amino acid；4-Fluorobenzoic acid；curcumin；the esterification reaction；The ester decomposition reaction
目录
1绪论 1
1.1课题背景 1
1.2天然产物化学研究 2
1.3姜黄素药理活性简述 2
1.3.1抗炎作用 2
1.3.2抗氧化作用 3
1.3.3抗肿瘤作用 3
1.3.4其他药理活性 3
1.4姜黄素及其衍生物合成研究 4
1.4.1姜黄素的构效关系（SAR）研究 4
1.4.2姜黄素及其衍生物研究进展 4
1.5氟化学简介 7
1.6氟对药物分子的影响 8
1.6.1氟对药物分子酸碱度的影响 8
1.6.2氟对药物分子脂溶性的影响 9
1.6.3氟对药物药性的影响 9
1.7常用酯化反应的方法 10
1.8肽键的形成 10
1.9酯的水解机理 12
1.10本课题研究内容与方向 13
2实验部分 17
2.1主要实验试剂及主要实验仪器 17
2.1.1主要实验试剂 17
2.1.2主要实验仪器 17
2.2实验步骤 18
2.2.1以L-苯丙氨酸为原料的含氟修饰的姜黄素衍生物的合成 18
2.2.2以L-缬氨酸为原料的含氟修饰的姜黄素衍生物的合成 20
3结果与讨论 22
3.1酯水解反应条件的确定 22
3.2氟修饰姜黄素衍生分离条件的选择与确定 22