Design, synthesis and bioevaluation of two series of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines

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Title
Design, synthesis and bioevaluation of two series of 3-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines
Author(s)
T T Lan; D T Anh; H Pham-The; D T M Dung; E J Park; S D Jang; Joo Hee KwonJong Soon Kang; N T Thuan; S B Han; N H Nam
Bibliographic Citation
Chemistry & Biodiversity, vol. 17, no. 7, pp. e2000290-e2000290
Publication Year
2020
Abstract
Two series of 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines were designed initially as potential acetylcholine esterase inhibitors. Biological evaluation demonstrated that N-(1-benzylpiperidin-4-yl)quinazolin-4-amines significantly inhibited AChE activity. Especially, two compounds of them were found to be the most potent with relative AChE inhibition percentages of 87 % in comparison to donepezil. The docking studies with AChE showed similar interactions between donepezil and four derivatives. N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines also exhibited significant DPPH scavenging effects. The two series of compound also exerted moderate to good cytotoxicity against three human cancer cell lines, including SW620 (human colon cancer), PC-3 (prostate cancer), and NCI-H23 (lung cancer), with 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one being the most cytotoxic agent. 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one significantly induced early apoptosis and arrested the SW620 cells at G2/M phase. From this study, two compounds of N-(1-benzylpiperidin-4-yl)quinazolin-4-amines could serve as new leads for further design and AChE inhibitors, while 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one could serve as a new lead for the design and development of more potent anticancer agents.
Keyword
acetylcholine esterase inhibitorsquinazolin-4(3H)-onequinazolin-4-aminecytotoxicitydocking simulation
ISSN
1612-1872
Publisher
Wiley
DOI
http://dx.doi.org/10.1002/cbdv.202000290
Type
Article
Appears in Collections:
Ochang Branch Institute > Division of Bioinfrastructure > Laboratory Animal Resource Center > 1. Journal Articles
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