Citation: Zhen-Gang Li, Guo-Qiang Dong, Sheng-Zheng Wang, Zhen-Yuan Miao, Jian-Zhong Yao, Wan-Nian Zhang, Chun-Quan Sheng. Optical evodiamine derivatives: Asymmetric synthesis and antitumor activity[J]. Chinese Chemical Letters, ;2015, 26(3): 267-271. doi: 10.1016/j.cclet.2014.11.011 shu

Optical evodiamine derivatives: Asymmetric synthesis and antitumor activity

1.
School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Corresponding author: Chun-Quan Sheng,
Received Date: 22 September 2014
Available Online: 23 October 2014
Fund Project: This work was supported by National Natural Science Foundation of China (Nos. 81222044, 81373278) (Nos. 81222044, 81373278)

Evodiamine and its derivatives have an asymmetric center at the C13b position. Herein, isomers of evodiamine derivatives 2 and 3 were obtained by straightforward asymmetric total synthesis. Their inhibitory activities toward topoisomerases I and II and their cytotoxicities in cancer cell lines were evaluated. All the four isomers exhibited good to excellent antitumor potency and the (S)-isomers were generally more active than the (R)-isomers. The binding modes of (S)-2 with topoisomerases I and II were also clarified by molecular docking.
- Evodiamine derivatives,
- Topoisomerase I,
- Topoisomerase II,
- Asymmetric synthesis,
- Antitumor activity
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沈阳化工大学材料科学与工程学院沈阳 110142