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Citation: XING Zhi-Heng, LYU Na, HE Zhong-Mei, GAO Yu-Gang, ZHAO Yan, ZHU Hong-Yan, YANG He, ZHANG Lian-Xue. Synthesis of Fibrauretin Derivatives and Their Inhibition on Acetylcholinesterase Activity[J]. Chinese Journal of Analytical Chemistry, ;2018, 46(5): 684-689. doi: 10.11895/j.issn.0253-3820.171239 shu

Synthesis of Fibrauretin Derivatives and Their Inhibition on Acetylcholinesterase Activity

College of Chinese Medicine Materials, Jilin Agricultural University, Changchun 130118, China

Received Date: 9 September 2017
Revised Date: 16 March 2018

Fund Project: This work was supported by the Jilin Province Science and Techndogy Development Plan Projeet (No.2018414072GH) and the First Batch of Young Talents Support Plan of Jilin Agricultural University.

The structure of fibrauretin made by our lab was modified. Fibrauretin was demethylated at 9-site under high temperature pyrolysis at 160℃-180℃ and was reacted with a series of acid chlorides. Twele derivatives of fibrauretin were obtained. The structure of each derivative was determined by¹H-NMR and¹³C-NMR. The derivatives were 9-O-benzoyl-fibrauretin, 9-O-(2-methylbenzoyl)-fibrauretin, 9-O-(4-methylbenzoyl)-fibrauretin, 9-O-(3,5-dimethylbenzoyl)-fibrauretin, 9-O-(4-(chloromethyl)benzoyl)-fibrauretin and other derivatives. The 12 derivatives are all new chemical compounds. Taking ATCI as substrate, the inhibitory activity on acetylcholinesterase (AChE) from the head of flies of the fibrauretin and its derivatives were screened. The results showed that most of the derivatives had improved their inhibitory activity on AChE through esterification reaction. Compounds 9-O-(4-methylbenzoyl)-fibrauretin, 9-O-(3,5-dimethylbenzoyl)-fibrauretinand 9-O-(4-(chloromethyl)benzoyl)-fibrauretin had significant inhibitory effect on AChE, and the inhibitory activity was stronger than the that of donepezil.
- Fibrauretin,
- Esterification reaction,
- Acetylcholinesterase,
- Inhibitory activity
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