Design, Synthesis, and Biological Activity of Novel 1,3,5-Triazine–1,2,4-Triazine Hybrids as Cholinesterase Inhibitors

Fourteen 1,3,5-triazine–1,2,4-triazine hybrids were designed and synthesized. Their structures were confirmed by IR, NMR, and high-resolution mass spectra, as well as by single crystal X-ray diffraction. The cholinesterase inhibitory activities of the hybrids were assayed by Ellman’s method. Five of...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-09, Vol.59 (9), p.1610-1619
Main Authors: Dong, Chang-E., Li, Rui, Pan, Zai-Xiu, Li, He, Qian, Jing-Jing, Liu, Wei-Wei, Cao, Zhi-Ling, Shi, Da-Hua
Format: Article
Language:English
Subjects:
Biological activity
Chemistry
Chemistry and Materials Science
Cholinesterase
Mass spectra
Molecular docking
NMR
Nuclear magnetic resonance
Organic Chemistry
Single crystals
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Summary:Fourteen 1,3,5-triazine–1,2,4-triazine hybrids were designed and synthesized. Their structures were confirmed by IR, NMR, and high-resolution mass spectra, as well as by single crystal X-ray diffraction. The cholinesterase inhibitory activities of the hybrids were assayed by Ellman’s method. Five of the fourteen hybrids inhibited acetylcholinesterase by more than 50% at a concentration of 50 μM. Only two hybrids inhibited butyrylcholinesterase by more than 50% at a concentration of 50 μM. Compound 5c possessed the best acetyl­cholinesterase and butyrylcholinesterase inhibitory activities with IC 50 of 6.80±0.14 μM and 1.91±0.12 μM, respectively. Molecular docking showed that compound 5c interacted with both catalytic active site and peripheral anionic site of acetylcholinesterase.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023090191