Citation: Jingyuan He, Zekai Wang, Xianwei Qi, Kaiyuan Chen, Jiang Bian. Application and Prospect of Molecular Skeletal Editing in Drug Synthesis[J]. University Chemistry, ;2023, 38(10): 313-323. doi: 10.3866/PKU.DXHX202301033 shu

Application and Prospect of Molecular Skeletal Editing in Drug Synthesis

1.
College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;
2.
School of Physics, Peking University, Beijing 100871, China

Corresponding author: Jiang Bian, bj@pku.edu.cn
Received Date: 26 January 2023
Revised Date: 8 May 2023

Molecular editing, including peripheral and skeletal editing, is an area of interest in the field of organic synthesis. Typically, the peripheral editing of C―H bonds is conventionally used for molecular editing. By contrast, skeletal editing is a novel method, which has broader applications in total synthesis and drug development, with advantages of easy operation, high specificity, and simple synthetical routes. This review introduces two skeletal editing examples using common reactions. By comparisons with conventional methods, the applications of molecular editing in drug synthesis are revealed. Moreover, this review predicts the future applications of molecular editing by presenting some state-of-the-art developments in this field.
- Molecular editing,
- Skeletal editing,
- Drug synthesis,
- Drug development
1. [1]
  Kennedy, S. H.; Dherange, B. D.; Berger, K. J.; Levin, M. D. Nature 2021, 593, 223.
2. [2]
  Dherange, B. D.; Kelly, P. Q.; Liles, J. P.; Sigman, M. S.; Levin, M. D. J. Am. Chem. Soc. 2021, 143, 11337.
3. [3]
  -499.
4. [4]
  Woo, J.; Christian, A. H.; Burgess, S. A.; Yuan, J.; Mansoor, U. F.; Levin, M. D. Science 2022, 376, 527.
5. [5]
  Reisenbauer, J. C.; Green, O.; Franchino, A.; Finkelstein, P.; Morandi, B. Science 2022, 377, 1104.
6. [6]
  Qin, H.; Cai, W.; Wang, S.; Guo, T.; Li, G.; Lu, H. Angew. Chem. Int. Ed. 2021, 60, 20678.
7. [7]
  Zippel, C.; Seibert, J.; Bräse, S. Angew. Chem. Int. Ed. 2021, 60, 19522.
8. [8]
  Lyu, H.; Kevlishvili, I.; Yu, X.; Liu, P.; Dong, G. Science 2021, 372, 175.
9. [9]
  Patel, S. C.; Burns, N. Z. J. Am. Chem. Soc. 2022, 144, 17797.
10. [10]
  Hui, C.; Antonchick, A. P. Bioorg. Med. Chem. 2022, 67, 116817.
11. [11]
  Ma, D.; Martin, B. S.; Gallagher, K. S.; Saito, T.; Dai, M. J. Am. Chem. Soc. 2021, 143, 16383.
12. [12]
  Yuan, P.; Gerlinger, C. K. G.; Herberger, J.; Gaich, T. J. Am. Chem. Soc. 2021, 143, 11934.
13. [13]
  Fu, C.; Zhang, Y.; Xuan, J.; Zhu, C.; Wang, B.; Ding, H. Org. Lett. 2014, 16, 3376.
14. [14]
  Fischer, D. F.; Sarpong, R. J. Am. Chem. Soc. 2010, 132, 5926.
15. [15]
16. [16]
  Kröhnk, F. Angew. Chem. Int. Ed. 1963, 2, 225.
17. [17]
  Yuan, C.; Chang, C.; Siegel, D. J. Org. Chem. 2013, 78, 5647.
18. [18]
  Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Am. Chem. Soc. 2010, 132, 5924.
19. [19]
  Nakamura, M.; Chi, Y.; Yan, W.; Yonezawa, A.; Nakasugi, Y.; Yoshizawa, T.; Hashimoto, F.; Kinjo, J.; Nohara, T.; Sakurada, S.Planta Med. 2001, 67, 114.
20. [20]
  Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076.
21. [21]
  Hu, J.; Feng, L.; Wang, L.; Xie, Z.; Tang, Y.; Li, X. J. Am. Chem. Soc. 2016, 138, 13151.
22. [22]
  Pachaly, B.; West, R. Angew. Chem. Int. Ed. 1984, 23, 454.
23. [23]
  Jurczyk, J.; Woo, J.; Kim, S. F.; Dherange, B. D.; Sarpong, R.; Levin, M. D. Nat. Synth. 2022, 1, 352.
24. [24]
  Golding, B. T. The Story of Rucaparib (Rubraca). In Successful Drug Discovery; Fischer, J., Klein, C., Childers, W. E., Eds.; Wiley-VCH:Weinheim, Germany, 2019; pp. 201-223.
25. [25]
  Fout, A. R.; Bailey, B. C.; Tomaszewski, J.; Mindiola, D. J. J. Am. Chem. Soc. 2007, 129, 12640.
26. [26]
  Morofuji, T.; Inagawa, K.; Kano, N. Org. Lett. 2021, 23, 6126.
27. [27]
  Holovach, S.; Melnykov, K. P.; Poroshyn, I.; Iminov, R. T.; Dudenko, D.; Kondratov, I.; Levin, M.; Grygorenko, O. O. Chem. Eur. J. 2023, 29, e202203470.
28. [28]
  Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
1. [1]
  Yuanyuan Zeng , Xiaoti Chang , Jingru Li , Qilin Wang . 骨架编辑策略：异喹啉到2-氨基-1-萘甲醛的转化. University Chemistry, 2026, 41(10): 309-315. doi: 10.12461/PKU.DXHX202510028
2. [2]
  Fen Tan , Cong Xiong , Yu-Xuan Ni , Zhihan Zhang , Ke Gao , Wen-Jing Xiao , Liang-Qiu Lu . Carbene chemistry teaching integrated with cutting-edge single-atom skeletal editing of indoles: a case study in organic chemistry education under the “101 Plan”. University Chemistry, 2026, 41(6): 53-59. doi: 10.12461/PKU.DXHX202506066
3. [3]
  Yuxia Luo , Xiaoyu Xie , Fangfang Chen . 药物递送魔法师——分子印迹聚合物. University Chemistry, 2025, 40(8): 202-210. doi: 10.12461/PKU.DXHX202409129
4. [4]
  Xiuya Ma , Yu Chen , Yan Zhang . Stories about Pharmaceuticals. University Chemistry, 2025, 40(7): 232-240. doi: 10.12461/PKU.DXHX202408003
5. [5]
  Weizhe Liu , Minghui Shi , Ruiqi Zhu , Bin Pan , Guofu Huang . 抗癌药物艾乐替尼的生物电子等排体的合成. University Chemistry, 2026, 41(5): 210-221. doi: 10.12461/PKU.DXHX202510066
6. [6]
  Ziheng Zhuang , Xiao Xu , Kin Shing Chan . Superdrugs for Superbugs. University Chemistry, 2024, 39(9): 128-133. doi: 10.3866/PKU.DXHX202309040
7. [7]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
8. [8]
  Zheqi Wang , Yawen Lin , Shunliu Deng , Huijun Zhang , Jinmei Zhou . Antiviral Strategies: A Brief Review of the Development History of Small Molecule Antiviral Drugs. University Chemistry, 2024, 39(9): 85-93. doi: 10.12461/PKU.DXHX202403108
9. [9]
  Zhifang SU , Zongjie GUAN , Yu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290
10. [10]
  Peng Zhan . Practice and Reflection in Training Medicinal Chemistry Graduate Students. University Chemistry, 2024, 39(6): 112-121. doi: 10.3866/PKU.DXHX202402022
11. [11]
  Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039
12. [12]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
13. [13]
  Tangsheng Guan , Ruizhi Yang , Pingyue Geng , Yuhong Lin , Shui Hu , Xiaojuan Chen , Houjin Li , Yong Shen . Innovative Digital Experiments for Glutathione-Targeted Anticancer Drugs in Redox Systems. University Chemistry, 2026, 41(1): 144-158. doi: 10.12461/PKU.DXHX202505028
14. [14]
  Qiang MA , Yiming ZHU , Meiqi HUA , Guangyu LU , Xingdong WANG , Hailong YU , Huan PANG , Yuping LI . Research progress on metal-organic frameworks as comprehensive carrier platforms for delivering anti-glioma drugs. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 657-667. doi: 10.11862/CJIC.20250250
15. [15]
  Qin Liu , Shuang Wu , Wenlong Xu , Xuyue Zhang , Huili Fan , Junze Song , Bo Wu , Chuanrun Li . 中药秘方还是化学激素——探究药物化学成分的综合性实验设计. University Chemistry, 2026, 41(10): 326-335. doi: 10.12461/PKU.DXHX202510046
16. [16]
  Hujun Qian , Rui Shi , Guanglu Wu , Xuanbo Zhu . A Preliminary Study on the Development of a Virtual Simulation Platform for Polymer Physics Teaching and Its Teaching Practice. University Chemistry, 2025, 40(4): 147-153. doi: 10.12461/PKU.DXHX202409009
17. [17]
  Xiaoxuan Yu , Wukun Liu . Practice of Ideological and Political Education in Medicinal Chemistry for Pharmacy Administration Major: A Case Study on the Discovery of Cisplatin’s Anticancer Function. University Chemistry, 2025, 40(4): 408-414. doi: 10.12461/PKU.DXHX202405200
18. [18]
  Lin LI , Jiaxue LI , Meixia YANG , Jiayu DING , Jiaqi JING , Ruiping ZHANG . Preparation of mitoxantrone self-assembled carrier-free nanodrugs regulated by sodium acetate for apoptosis induction of human breast carcinoma cells. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2536-2548. doi: 10.11862/CJIC.20250138
19. [19]
  Peihong Fan , Hongxiang Lou . 研究生高等天然药物化学课程的教学改革探索——导学互促式混合课堂教学与自主学习能力培养. University Chemistry, 2025, 40(6): 16-21. doi: 10.12461/PKU.DXHX202407078
20. [20]
  . Synthesis and properties of metal‐organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1-2.

Get Citation

PDF

XML

Metrics

PDF Downloads(26)
Abstract views(2145)
HTML views(284)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142