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Citation: Ju Guo, Yi Gao, Shimin Hu, Ke Fan, Sihui Long. 6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸甲酯的制备——介绍一个大学药物化学综合实验[J]. University Chemistry, ;2022, 37(6): 220103. doi: 10.3866/PKU.DXHX202201038 shu

6,7-二甲氧基-1,2,3,4-四氢异喹啉-3-羧酸甲酯的制备——介绍一个大学药物化学综合实验

Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205, China

Corresponding author: Ju Guo, guoju1984@163.com
Received Date: 19 January 2022

介绍了我校制药工程专业和药物制剂专业开展的一个综合药物化学实验，该实验以合成PARP1抑制剂的关键中间体6，7-二甲氧基-1，2，3，4-四氢异喹啉-3-羧酸甲酯为目标分子，该化合物是作者课题组目前正在研究的PARP1抑制剂的关键中间体，其合成方法是以L-3，4-二甲氧基苯丙氨酸为原料，甲醇为溶剂，二氯亚砜为脱水剂，室温条件下合成L-3，4-二甲氧基苯丙氨酸甲酯，再以多聚甲醛为原料，二氯甲烷为溶剂，三氟乙酸为催化剂，经Pictet-Spengler反应合成6，7-二甲氧基-1，2，3，4-四氢异喹啉-3-羧酸甲酯，目标化合物的结构使用¹H NMR、MS等分析方法进行表征。本实验有益于激发学生独立思考能力和研究意识，训练学生的综合实验操作技能和有机化合物的结构鉴定能力，培养学生掌握药物合成科学研究的基本思路和基本方法。
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
  Faheem; Kumar, B. K.; Sekhar, K. V. G. C.; Chander, S.; Kunjiappan, S.; Murugesan, S. Expert. Opin. Drug. Discov. 2021, 16 (10), 1119.
6. [6]
  Pietro, C.; Isabel, G.; Teresa, L.; Ettore, N.; Paolo, G. Molec. Diver. 2004, 8, 42.
7. [7]
  Xu, G.; Liu, Z. Z. Chin. Chem. Lett. 2009, 20, 1393.
8. [8]
  Guo, J.; Dong, W.-F.; Liu, W.; Yan, Z.; Wang, N.; Liu, Z.-Z. Eur. J. Med. Chem. 2013, 62, 670.
9. [9]
  Guo, J.; Yang, Y.; Wang, N.; Liu, Z.-Z. Tetrahedron Lett. 2018, 33, 3202.
1. [1]
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