脱氢枞基伯胺衍生物的合成及其抗癌活性研究  

Synthesis and Anticancer Activity of Dehydroabietyl Primary Amine Derivatives

作　　者：齐志文 王成章[1,2,3,4] 蒋建新 QI Zhiwen;WANG Chengzhang;JIANG Jianxin(Institute of Chemical Industry of Forest Products,CAF;National Engineering Lab.for Biomass Chemical Utilization;Key and open Lab.of Forest Chemical Engineering,SFA;Key Lab.of Biomass Energy and Material,Jiangsu Province,Nanjing210042,China;College of Materials Science and Technology,Beijing Forestry University,Beijing100083,China)

机构地区：[1]中国林业科学研究院林产化学工业研究所 [2]生物质化学利用国家工程实验室 [3]国家林业局林产化学工程重点开放性实验室 [4]江苏省生物质能源与材料重点实验室,江苏南京210042 [5]北京林业大学材料科学与技术学院,北京100083

出　　处：《林产化学与工业》2018年第6期117-123,共7页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(31570564);江苏省生物质能源与材料重点实验室基本科研业务费项目(JSBEM-S-201509)

摘　　要：以左旋海松酸(0.3 mmol)为原料、三乙胺(TEA)为碱、1-(3-二甲胺基丙基)-3-乙基碳二亚胺盐酸盐(EDCI)为脱水剂、1H-苯并三唑-1-基氧三吡咯烷基六氟磷酸盐/4-二甲氨基吡啶(n(PyBOP)∶n(DMAP)=0.03 mmol∶0.01 mmol)为催化剂、乙腈(MeCN)为溶剂,简单、高效地合成了脱氢枞基伯胺衍生物:脱氢枞酰胺甲酸(1),脱氢枞酰胺乙酸(2),脱氢枞酰胺丙酸(3),脱氢枞酰胺丁酸(4),并对其结构进行了表征,其中化合物3产率可达78%。经伯胺酰胺化后的化合物3对人胃癌MKN-45细胞株具有较高的增殖抑制活性,IC50值为31.26μmol/L。The primary amine derivatives of dehydroabietic acid:dehydroabietic amide formic acid(1),dehydroabietic amide acetic acid(2),dehydroabietic amide propionic acid(3)and dehydroabietic amide butyric acid(4)were synthesized by a simple and efficient one-pot method with levopimaric acid(0.3 mmol)as raw material,triethylamine(TEA)as base,1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride(EDCI)as dehydrant,1H benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate/4-dimethylamino pyridine(n(PyBOP)∶n(DMAP)=0.03 mmol∶0.01 mmol)as catalyst and acetonitrile as solvent.The yield of the compound 3 were up to 78%.The compound 3 modified by primary amine had a high proliferation inhibitory activity toward human gastric cancer MKN-45 cell line with the IC50 of 31.26μmol/L.

关 键 词：左旋海松酸 脱氢枞酸 羧基 位阻 伯胺 酰胺化 

分 类 号：TQ35[化学工程]