Citation: Li Sicong, Ji Shaocong, Zhao Liang, Liao Xiaoyu, Liu Chuanfeng, Tang Haodong, Shu Zhengning, Yang Peng, Pei Yuehu. Syntheses and Property Evaluation of N-Salicylaldehyde Hydrazone Modified 11-Azaartemisinins and Their Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2860-2866. doi: 10.6023/cjoc201902024 shu

Syntheses and Property Evaluation of N-Salicylaldehyde Hydrazone Modified 11-Azaartemisinins and Their Derivatives

a.
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016
b.
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016

Corresponding author: Yang Peng, yangpeng@syphu.edu.cn Pei Yuehu, peiyueh@vip.163.com
Received Date: 22 February 2019
Revised Date: 29 April 2019
Available Online: 6 October 2019
Fund Project: the Natural Science Foundation of Liaoning Province No. 20180550874Project supported by the Natural Science Foundation of Liaoning Province (No. 20180550874)

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N-Salicylaldehyde hydrazone modified 11-azaartemisinins and their deoxy analogues were designed and synthesized. By using various techniques including UV-vis, fluorescence, NMR as well as molecular modeling, the conformations of (3R, 5aS, 6R, 8aS, 9R, 12S, 12aR)-11-(((E)-2-hydroxy-5-(4-hydroxy-3-((E)-(((3R, 5aS, 6R, 8aS, 9R, 12R, 12aR)-3, 6, 9-trimethyl-10-oxodecahydro-3, 12-epoxy[1, 2]dioxepino[4, 3-i]isoquinolin-11(12H)-yl)imino)methyl)benzyl)benzylidene)amino)-3, 6, 9-trimethyldecahydro-3, 12-epoxy[1, 2]dioxepino[4, 3-i]isoquinolin-10(3H)-one (3) was analyzed, the binding behavior between 3 and hemin was measured, and the solubility-enhancing property of 3 by calix[4]carbazole was evaluated. The results show that the intramolecular hydrogen binding between the N atom of Schiff base in N-salicylaldehyde hydrazone bond and the OH favors the formation of tweezer-like conformation of 3, which enables it to interact with hemin in 1:1 ratio. Moreover, the poor solubility of 3 in water could be enhanced due to its interaction with calix[4]carbazole, which pave the way for the further evaluation of the bioactivities of 3 in the future.
- macrocycle,
- molecular recognition,
- carbazole,
- artemisinin,
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