Synthesis, characterization and biological activity of 3-aryl-6-(4-fluorobenzyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as novel acetylcholinesterase inhibitors

Henan Xu, Lan Zhang, Hongmin Liu, Sijie Liu, Huangquan Lin, Yan Wang, David Chi Cheong Wan, Chun Hu

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Acetylcholinesterase (AChE) inhibitors play an important role in the treatment of Alzheimer's disease. To study the effect of the presence of a fluoro group on inhibitory activity against AChE, a series of 3-aryl-6-(4-fluorobenzyl)-7H-thiazolo[3,2]-1,2,4-triazin-7-one derivatives have been synthesized, in which a hydrogen atom has been substituted by a fluorine in the aromatic nucleus of 6-arylmethyl-3-phenyl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives, a series of compounds previously reported by us to have inhibitory activity against acetylcholinesterase. From the molecular docking studies, it was found that, in general, a key hydrogen bond of target compounds to the OH of Tyr341 and a close contact with relevant residues in the catalytic site are prerequisites for high inhibitory activity.

Original languageEnglish (US)
Pages (from-to)953-959
Number of pages7
JournalLatin American Journal of Pharmacy
Volume32
Issue number7
StatePublished - Sep 10 2013

Fingerprint

Cholinesterase Inhibitors
Acetylcholinesterase
Hydrogen
Fluorine
Catalytic Domain
Alzheimer Disease
7H-thiazolo(3,2-b)-1,2,4-triazin-7-one

Keywords

  • 7H-thiazolo[32-b]-124-triazin-7-one derivatives
  • Acetylcholinesterase inhibitor
  • Docking
  • Fluorine substitution
  • Heterocycle
  • Synthesis

Cite this

Synthesis, characterization and biological activity of 3-aryl-6-(4-fluorobenzyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as novel acetylcholinesterase inhibitors. / Xu, Henan; Zhang, Lan; Liu, Hongmin; Liu, Sijie; Lin, Huangquan; Wang, Yan; Wan, David Chi Cheong; Hu, Chun.

In: Latin American Journal of Pharmacy, Vol. 32, No. 7, 10.09.2013, p. 953-959.

Research output: Contribution to journalArticle

Xu, Henan ; Zhang, Lan ; Liu, Hongmin ; Liu, Sijie ; Lin, Huangquan ; Wang, Yan ; Wan, David Chi Cheong ; Hu, Chun. / Synthesis, characterization and biological activity of 3-aryl-6-(4-fluorobenzyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as novel acetylcholinesterase inhibitors. In: Latin American Journal of Pharmacy. 2013 ; Vol. 32, No. 7. pp. 953-959.
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AU - Wan, David Chi Cheong

AU - Hu, Chun

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AB - Acetylcholinesterase (AChE) inhibitors play an important role in the treatment of Alzheimer's disease. To study the effect of the presence of a fluoro group on inhibitory activity against AChE, a series of 3-aryl-6-(4-fluorobenzyl)-7H-thiazolo[3,2]-1,2,4-triazin-7-one derivatives have been synthesized, in which a hydrogen atom has been substituted by a fluorine in the aromatic nucleus of 6-arylmethyl-3-phenyl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives, a series of compounds previously reported by us to have inhibitory activity against acetylcholinesterase. From the molecular docking studies, it was found that, in general, a key hydrogen bond of target compounds to the OH of Tyr341 and a close contact with relevant residues in the catalytic site are prerequisites for high inhibitory activity.

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